Skip to main content
SpringerLink
Log in

Camps Reaction and Related Cyclizations

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The review presents analysis of the literature on the intramolecular cyclization of N-(2-acylaryl)amides, known as the Camps reaction, as well as close analogs of these compounds, N-(3-oxoalkenyl)- and N-(3-oxoalkyl)amides, which contain an amide and a carbonyl groups and react by the aldol–crotonic type. The potential, limitations, and regularities of these reactions leading to quinoline-2(1H)-ones, quinoline-4(1H)-ones, pyridin-2-ones, pyridin-4-ones, as well as their hydrogenated derivatives are highlighted.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Prajapati, S.M., Patel, K.D., Vekariya, R.H., Panchal, S.N., and Patel, H.D., RSC Adv., 2014, vol. 4, p. 24463. https://doi.org/10.1039/C4RA01814A

    Article  CAS  Google Scholar 

  2. Heeb, S., Fletcher, M.P., Chhabra, R.S., Diggle, S.P., Williams, P., and Camara, M., FEMS Microbiol. Rev., 2011, vol. 35, p. 247. https://doi.org/10.1111/j.1574-6976.2010.00247

    Article  CAS  PubMed  Google Scholar 

  3. Horta, P., Secrieru, A., Coninckx, A., and Cristiano, M.L.S., Targets Heterocycl. Syst., 2018, vol. 11, p. 260. https://doi.org/10.17374/targets.2019.22.260

    Article  CAS  Google Scholar 

  4. Beteck, R.M., Smit, F.J., Haynes, R.K., and N’Da, D.D., Malar. J., 2014, vol. 13, p. 339. https://doi.org/10.1186/1475-2875-13-339

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Charushin, V.A., Nosova, E.V., Lyapunova, G.N., and Chupakhin, O.N., Ftorkhinoliny: sintez i primenenie (Fluoroquinolones: Synthesis and Application), Moscow: FIZMATLIT, 2013.

  6. Manske, R.H., Chem. Rev., 1942, vol. 30, p. 113. https://doi.org/10.1021/cr60095a006

    Article  CAS  Google Scholar 

  7. Jones, G., Comprehensive Heterocyclic Chemistry, Katritzky, A.R. and Rees, C.W., Eds. New York: Pergamon. 1997, vol. 2, p. 316.

  8. Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Comprehensive Heterocyclic Chemistry III, Amsterdam: Elsevier, 2008, vol. 7, p. 217.

  9. Sharma, R., Kour, P., and Kumar, A., J. Chem. Sci., 2018, vol. 130, p. 73. https://doi.org/10.1007/s12039-018-1466-8

    Article  CAS  Google Scholar 

  10. Kouznetsov, V.V., Méndez, L.Y.V., and Gómez, C.M.M., Curr. Org. Chem., 2005, vol. 9, p. 141. https://doi.org/10.2174/1385272053369196

    Article  CAS  Google Scholar 

  11. Camps, R., Ber. Dtsch. Chem. Ges., 1899, vol. 32, p. 3228. https://doi.org/10.1002/cber.18990320389

    Article  CAS  Google Scholar 

  12. Camps, R., Arch. Pharm., 1899, vol. 237, p. 659. https://doi.org/10.1002/ardp.18992370902

    Article  CAS  Google Scholar 

  13. Camps, R., Arch. Pharm., 1901, vol. 239, p. 591. https://doi.org/10.1002/ardp.19012390805

    Article  Google Scholar 

  14. Camps, R., Arch. Pharm., 1902, vol. 240, p. 135. https://doi.org/10.1002/ardp.19022400204

    Article  CAS  Google Scholar 

  15. Vatsuro, K.V. and Mishchenko, G.V., Imennye reaktsii v organicheskoi khimii (Name Reactions in Organic Chemistry), Moscow: Kimiya, 1976.

  16. Pflum, D.A., Name Reactions in Heterocyclic Chemistry, Li, J.J. and Corey, E.J., Eds. Hoboken: Wiley and Sons, 2005, p. 386.

  17. Li, J.J., Name Reactions. A Collection of Detailed Mechanisms and Synthetic Applications, 4th Edn. Berlin: Springer-Verlag, 2009, p. 92. https://doi.org/10.1007/978-3-642-01053-84

  18. Elderfield, R.C., Todd, W.H., and Gerber, S., Heterocyclic Compounds, Elderfield, R.C., Ed. New York: Wiley and Sons, 1957, p. 576.

  19. Fisyuk, A.S. and Bundel’, Yu.G., Chem. Heterocycl. Compd., 1999, vol. 35, p. 125. https://doi.org/10.1007/BF02251699

    Article  CAS  Google Scholar 

  20. Konovalov, A.I., Antipin, I.S., Burilov, V.A., Madzhidov, T.I., Kurbangalieva, A.R., Nemtarev, A.V., Solovieva, S.E., Stoikov, I.I., Mamedov, V.A., Zakharova, L.Ya., Gavrilova, E.L., Sinyashin, O.G., Balova, I.A., Vasilyev, A.V., Zenkevich, I.G., Krasavin, M.Yu., Kuznetsov, M.A., Molchanov, A.P., Novikov, M.S., Nikolaev, V.A., Rodina, L.L., Khlebnikov, A.F., Beletskaya, I.P., Vatsadze, S.Z., Gromov, S.P., Zyk, N.V., Lebedev, A.T., Lemenovskii, D.A., Petrosyan, V.S., Nenaidenko, V.G., Negrebetskii, V.V., Baukov, Yu.I., Shmigol’, T.A., Korlyukov, A.A., Tikhomirov, A.S., Shchektikhin, A.E., Traven’, V.F., Voskresenskii, L.G., Zubkov, F.I., Golubchikov, O.A., Semeikin, A.S., Berezin, D.B., Stuzhin, P.A., Filimonov, V.D., Krasnokutskaya, E.A., Fedorov, A.Yu., Nyuchev, A.V., Orlov, V.Yu., Begunov, R.S., Rusakov, A.I., Kolobov, A.V., Kofanov, E.R., Fedotova, O.V., Egorova, A.Yu., Charushin, V.N., Chupakhin, O.N., Klimochkin, Yu.N., Osyanin, V.A., Reznikov, A.N., Fisyuk, A.S., Sagitullina, G.P., Aksenov, A.V., Aksenov, N.A., Grachev, M.K., Maslennikova, V.I., Koroteev, M.P., Brel’, A.K., Lisina, S.V., Medvedeva, S.M., Shikhaliev, Kh.S., Suboch, G.A., Tovbis, M.S., Mironovich, L.M., Ivanov, S.M., Kurbatov, S.V., Kletskii, M.E., Burov, O.N., Kobrakov, K.I., and Kuznetsov, D.N., Russ. J. Org. Chem., 2018, vol. 54, p. 157. https://doi.org/10.1134/S107042801802001X

    Article  CAS  Google Scholar 

  21. Lechel, T. and Reissig, H.-U., Targets in Heterocyclic Systems – Chemistry and Properties, Attanasi, O.A., Merino, P., and Spinelli, D., Eds., Rome: Italian Society of Chemistry, 2016, vol. 20, p. 1. https://doi.org/10.17374/targets.2017.20.1

  22. Bischler, A. and Howell, F.J., Ber. Dtsch. Chem. Ges., 1893, vol. 26, p. 1384. https://doi.org/10.1002/cber.18930260239

    Article  Google Scholar 

  23. Bieshler, A. and Lang, Y., Ber. Dtsch. Chem. Ges., 1895, vol. 28, p. 279. https://doi.org/10.1002/cber.18950280169

    Article  Google Scholar 

  24. Hewawasam, P., Fan, W., Ding, M., Flint, K., Cook, D., Goggins, G.D., Myers, R.A., Gribkoff, V.K., Boissard, C.G., Dworetzky, S.I., Starrett, J.E., and Lodge, N.J., J. Med. Chem., 2003, vol. 46, p. 2819. https://doi.org/10.1021/jm030005h

    Article  CAS  PubMed  Google Scholar 

  25. Wang, J.J., Discordia, R.P., Crispino, G.A., Li, J., Grosso, J.A., Polniaszek, R., and Truc, V.C., Tetrahedron Lett., 2003, vol. 44, p. 4271. https://doi.org/10.1016/S0040-4039(03)00889-X

    Article  CAS  Google Scholar 

  26. Hameršak, Z., Litvić, M., Šepac, D., Lesac, A., Raza, Z., and Šunjić, V., Synthesis, 2002, vol. 15, p. 2174. https://doi.org/10.1055/s-2002-34835

    Article  Google Scholar 

  27. Patel, M., McHugh, R.J., Cordova, B.C., Klabe, R.M., Bacheler, L.T., Erickson-Viitanen, S., and Rodgers, J.D., Bioorg. Med. Chem. Lett. 2001, vol. 11, p. 1943. https://doi.org/10.1016/S0960-894x(01)00331-6

  28. Mitchell, L.H. and Samas, B., Synth. Commun., 2005, vol. 35, p. 955. https://doi.org/10.1081/Scc-200051700

    Article  CAS  Google Scholar 

  29. Brouillette, Y., Martinez, J., and Lisowski, V., J. Org. Chem., 2009, vol. 74, p. 4975. https://doi.org/10.1021/jo900627a

    Article  CAS  PubMed  Google Scholar 

  30. Rehwald, M., Bellmann, P., Jeschke, T., and Gewald, K., J. Prakt. Chem., 2000, vol. 342, p. 371. https://doi.org/10.1002/(Sici)1521-3897(200004)342:4<371::Aid-Prac371>3.0.Co;2-M

    Article  CAS  Google Scholar 

  31. Yanagisawa, H., Nakao, H., and Ando, A., Chem. Pharm. Bull., 1973, vol. 21, p. 1080. https://doi.org/10.1248/cpb.21.1080

    Article  CAS  Google Scholar 

  32. Manley, P.J. and Bilodeau, M.T., Org. Lett., 2004, vol. 6, p. 2433. https://doi.org/10.1021/ol049165t

    Article  CAS  PubMed  Google Scholar 

  33. Ban, H., Muraoka, M., Morisita, K., and Ohashi, N., Heterocycles, 2005, vol. 65, p. 2763. https://doi.org/10.3987/Com-05-10511

    Article  CAS  Google Scholar 

  34. Amer, A.M., Monatsh. Chem., 2001, vol. 132, p. 859. https://doi.org/10.1007/s007060170075

    Article  CAS  Google Scholar 

  35. Gorelik, M.V., Titova, S.P., and Gordievskaya, E.V., Russ. Chem. Bull., 2006, vol. 55, p. 1487. https://doi.org/10.1007/s11172-006-0444-3

    Article  CAS  Google Scholar 

  36. Ibrahim, H.M., Behbehani, H., Makhseed, S., and Elnagdi, M.H., Molecules, 2011, vol. 16, p. 3723. https://doi.org/10.3390/molecules16053723

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Peters, J.U., Capuano, T., Weber, S., Kritter, S., and Sagesser, M., Tetrahedron Lett., 2008, vol. 49, p. 4029. https://doi.org/10.1016/j.tetlet.2008.04.088

    Article  CAS  Google Scholar 

  38. El Mariah, F., J. Chem. Res., 2009, p. 593. https://doi.org/10.3184/030823409x12508790019612

  39. Mochalov, S.S., Chasanov, M.I., Fedotov, A.N., and Zefirov, N.S., Chem. Heterocycl. Compd., 2011, vol. 47, p. 1105. https://doi.org/10.1007/s10593-011-0881-2

    Article  CAS  Google Scholar 

  40. Park, K.K. and Lee, J.J., Tetrahedron, 2004, vol. 60, p. 2993. https://doi.org/10.1016/j.tet.2004.02.001

    Article  CAS  Google Scholar 

  41. Mochalov, S.S., Fedotov, A.N., Trofimova, E.V., and Zefirov, N.S., Russ. J. Org. Chem., 2016, vol. 52, p. 956. https://doi.org/10.1134/S107042801607006x

    Article  CAS  Google Scholar 

  42. Park, K.K. and Jung, J.Y., Heterocycles, 2005, vol. 65, p. 2095. https://doi.org/10.3987/COM-05-10462

    Article  CAS  Google Scholar 

  43. Jones, C.P., Anderson, K.W., and Buchwald, S.L., J. Org. Chem., 2007, vol. 72, p. 7968. https://doi.org/10.1021/jo701384n

    Article  CAS  PubMed  Google Scholar 

  44. Wӧhnlich, E., Arch. Pharm., 1913, vol. 251, p. 526. https://doi.org/10.1002/ardp.19132510606

    Article  Google Scholar 

  45. Kutsumura, N., Numata, K., and Saito, T., Tetrahedron Lett., 2016, vol. 57, p. 5581. https://doi.org/10.1016/j.tetlet.2016.10.070

    Article  CAS  Google Scholar 

  46. Eidamshaus, C., Triemer, T., and Reissig, H.U., Synthesis, 2011, p. 3261. https://doi.org/10.1055/s-0030-1260198

  47. Witkop, B., Patrick, J.B., and Rosenblum, M., J. Am. Chem. Soc., 1951, vol. 73, p. 2641. https://doi.org/10.1021/ja01150a065

    Article  CAS  Google Scholar 

  48. Hayward, R.J. and Methcohn, O., J. Chem. Soc. Perkin Trans. 1, 1975, p. 212. https://doi.org/10.1039/p19750000212

  49. Afsah, E.M., Fadda, A.A., Bondock, S., and Hammouda, M.M., Z. Naturforsch. B, 2015, vol. 70, p. 385. https://doi.org/10.1515/znb-2014-0271

    Article  CAS  Google Scholar 

  50. Willemsens, B., Vervest, I., Ormerod, D., Aelterman, W., Fannes, C., Mertens, N., Marko, I.E., and Lemaire, S., Org. Process Res. Dev., 2006, vol. 10, p. 1275. https://doi.org/10.1021/op060099f

    Article  CAS  Google Scholar 

  51. Liu, S., Scotti, J.S., and Kozmin, S.A., J. Org. Chem. 2013, vol. 78, p. 8645. https://doi.org/10.1021/jo401262v

  52. Demerson, C.A. and Humber, L.G., Can. J. Chem., 1979, vol. 57, p. 3296. https://doi.org/10.1139/v79-538

    Article  CAS  Google Scholar 

  53. Lemaire, S., Willemsens, B., and Marko, I.E., Synlett, 2007, p. 709. https://doi.org/10.1055/s-2007-970769

  54. Barret, R., Ortillon, S., Mulamba, M., Laronze, J.Y., Trentesaux, C., and Levy, J., J. Heterocycl. Chem., 2000, vol. 37, p. 241. https://doi.org/10.1002/jhet.5570370204

    Article  CAS  Google Scholar 

  55. Desmaële, D., Tetrahedron Lett., 1996, vol. 37, p. 1233. https://doi.org/10.1016/0040-4039(96)00007-X

    Article  Google Scholar 

  56. Szamosvari, D. and Bottcher, T., Angew. Chem., Int. Ed., 2017, vol. 56, p. 7271. https://doi.org/10.1002/anie.201702944

    Article  CAS  Google Scholar 

  57. Abe, H., Kawada, M., Inoue, H., Ohba, S., Masuda, T., Hayashi, C., Igarashi, M., Nomoto, A., Watanabe, T., and Shibasaki, M., Tetrahedron, 2013, vol. 69, p. 7608. https://doi.org/10.1016/j.tet.2013.05.033

    Article  CAS  Google Scholar 

  58. Abe, H., Kawada, M., Igarashi, M., Ohba, S., Hayashi, C., Sakashita, C., Watanabe, T., and Shibasaki, M., J. Antibiot., 2018, vol. 71, p. 86. https://doi.org/10.1038/ja.2017.123

    Article  CAS  Google Scholar 

  59. Fackler, P., Huber, S.M., and Bach, T., J. Am. Chem. Soc., 2012, vol. 134, p. 12869. https://doi.org/10.1021/ja305890c

    Article  CAS  PubMed  Google Scholar 

  60. Mochalov, S.S., Fedotov, A.N., Trofimova, E.V., and Zefirov, N.S., Chem. Heterocycl. Compd., 2014, vol. 49, p. 1469. https://doi.org/10.1007/s10593-014-1398-2

    Article  CAS  Google Scholar 

  61. Clémence, F., Lemartret, O., and Collard, J., J. Heterocycl. Chem., 1984, vol. 21, p. 1345. https://doi.org/10.1002/jhet.5570210520

    Article  Google Scholar 

  62. Szamosvari, D., Sylvester, K., Schmid, P., Lu, K.Y., Derbyshire, E.R., and Bottcher, T., Chem. Commun., 2019, vol. 55, p. 7009. https://doi.org/10.1039/c9cc01689a

    Article  CAS  Google Scholar 

  63. Hadjeri, M., Mariotte, A.M., and Boumendjel, A., Chem. Pharm. Bull., 2001, vol. 49, p. 1352. https://doi.org/10.1248/cpb.49.1352

    Article  CAS  Google Scholar 

  64. Kumar, S., Verma, N., Zubair, S., Faisal, S.M., Kazmi, S., Chakraborty, S., Owais, M., and Ahmed, N., J. Heterocycl. Chem., 2017, vol. 54, p. 2242. https://doi.org/10.1002/jhet.2812

    Article  CAS  Google Scholar 

  65. Gao, H. and Kawabata, J., Bioorg. Med. Chem., 2005, vol. 13, p. 1661. https://doi.org/10.1016/j.bmc.2004.12.010

    Article  CAS  PubMed  Google Scholar 

  66. Nilsson, J., Nielsen, E.O., Liljefors, T., Nielsen, M., and Sterner, O., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 5713. https://doi.org/10.1016/j.bmcl.2008.09.092

    Article  CAS  PubMed  Google Scholar 

  67. Manfroni, G., Gatto, B., Tabarrini, O., Sabatini, S., Cecchetti, V., Giaretta, G., Parolin, C., Del Vecchio, C., Calistri, A., Palumbo, M., and Fravolini, A., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 714. https://doi.org/10.1016/j.bmcl.2008.12.034

    Article  CAS  PubMed  Google Scholar 

  68. Bera, S.S., Sk, M.R., and Maji, M.S., Chem. Eur. J., 2019, vol. 25, p. 1806. https://doi.org/10.1002/chem.201805376

    Article  CAS  PubMed  Google Scholar 

  69. Jiang, C., Yang, L., Wu, W.T., Guo, Q.L., and You, Q.D., Bioorg. Med. Chem., 2011, vol. 19, p. 5612. https://doi.org/10.1016/j.bmc.2011.07.029

    Article  CAS  PubMed  Google Scholar 

  70. Takami, H., Kishibayashi, N., Ishii, A., and Kumazawa, T., Bioorg. Med. Chem., 1998, vol. 6, p. 2441. https://doi.org/10.1016/S0968-0896(98)80018-7

    Article  CAS  PubMed  Google Scholar 

  71. Popova, N.N., Kulikov, S.V., and Piotrovskii, L.B., Russ. J. Gen. Chem., 2004, vol. 74, p. 1467. https://doi.org/10.1007/s11176-005-0037-0

    Article  CAS  Google Scholar 

  72. Chang, Y.H., Hsu, M.H., Wang, S.H., Huang, L.J., Qian, K., Morris-Natschke, S.L., Hamel, E., Kuo, S.C., and Lee, K.H., J. Med. Chem., 2009, vol. 52, p. 4883. https://doi.org/10.1021/jm900456w

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  73. Huang, J., Chen, Y., King, A.O., Dilmeghani, M., Larsen, R.D., and Faul, M.M., Org. Lett., 2008, vol. 10, p. 2609. https://doi.org/10.1021/ol800837z

    Article  CAS  PubMed  Google Scholar 

  74. Sui, Z.H., Nguyen, V.N., Altom, J., Fernandez, J., Hilliard, J.J., Bernstein, J.I., Barrett, J.F., and Ohemeng, K.A., Eur. J. Med. Chem., 1999, vol. 34, p. 381. https://doi.org/10.1016/S0223-5234(99)80087-7

    Article  CAS  Google Scholar 

  75. Beney, C., Hadjeri, M., Mariotte, A.M., and Boumendjel, A., Tetrahedron Lett., 2000, vol. 41, p. 7037. https://doi.org/10.1016/S0040-4039(00)01226-0

    Article  CAS  Google Scholar 

  76. Kobayashi, K., Nishikawa, K., and Nogi, T., Heterocycles, 2016, vol. 92, p. 2225. https://doi.org/10.3987/Com-16-13566

    Article  CAS  Google Scholar 

  77. Jensen, S. and Torssell, K.B.G., Acta Chem. Scand., 1995, vol. 49, p. 53. https://doi.org/10.3891/acta.chem.scand.49-0053

    Article  CAS  Google Scholar 

  78. Kapti, T., Dengiz, C., and Balci, M., Synthesis, 2017, vol. 49, p. 1898. https://doi.org/10.1055/s-0036-1588119

    Article  CAS  Google Scholar 

  79. Kim, G. and Keum, G., Heterocycles, 1997, vol. 45, p. 1979. https://doi.org/10.3987/COM-96-7676

    Article  CAS  Google Scholar 

  80. Kim, S.H., Jeong, J.U., Choi, D.O., and Lee, K.J., Bull. Korean Chem. Soc., 1993, vol. 14, p. 11. https://doi.org/10.1002/chin.199346179

    Article  CAS  Google Scholar 

  81. Alkhathlan, H.Z. and Al-Farhan, K.A. Heterocycles, 1998, vol. 48, p. 641. https://doi.org/10.3987/COM-97-7949

    Article  CAS  Google Scholar 

  82. Alkhathlan, H.Z., Al-Jaradah, M.A., Al-Farhan, K.A., and Mousa, A.A., Phosphorus, Sulfur Silicon Relat. Elem., 2004, vol. 179, p. 373. https://doi.org/10.1080/10426500490262513

    Article  CAS  Google Scholar 

  83. Khalikov, I.G., Galin, F.Z., Sakhautdinov, I.M., and Tukhvatullin, O.R., Baskir. Khim. Zh., 2007, vol. 14, p. 22.

    CAS  Google Scholar 

  84. Peifer, C., Urich, R., Schattel, V., Abadleh, M., Rottig, M., Kohlbacher, O., and Laufer, S., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 1431. https://doi.org/10.1016/j.bmcl.2007.12.073

    Article  CAS  PubMed  Google Scholar 

  85. Krayushkin, M.M., Lichitskii, B.V., Pashchenko, D.V., Antonov, I.A., Nabatov, B.V., and Dudinov, A.A., Russ. J. Org. Chem. 2007, vol. 43, p. 1357. https://doi.org/10.1134/S1070428007090163

  86. Mendez, M.V., Heredia, D.A., Larghi, E.L., Bracca, A.B.J., and Kaufman, T.S., RSC Adv., 2017, vol. 7, p. 28298. https://doi.org/10.1039/c7ra05349e

    Article  CAS  Google Scholar 

  87. Doleans-Jordheim, A., Veron, J.B., Fendrich, O., Bergeron, E., Montagut-Romans, A., Wong, Y.S., Furdui, B., Freney, J., Dumontet, C., and Boumendjel, A., ChemMedChem, 2013, vol. 8, p. 652. https://doi.org/10.1002/cmdc.201200551

    Article  CAS  PubMed  Google Scholar 

  88. Zheng, J., Li, Z., Wu, W.Q., and Jiang, H.F., Org. Lett., 2016, vol. 18, p. 6232. https://doi.org/10.1021/acs.orglett.6b02710

    Article  CAS  PubMed  Google Scholar 

  89. Yan, J., Pang, Y.Q., Chen, J., Sheng, J.F., Hu, J.H., Huang, L., and Li, X.S., RSC Adv., 2015, vol. 5, p. 98527. https://doi.org/10.1039/c5ra19270f

    Article  CAS  Google Scholar 

  90. Peifer, C., Kinkel, K., Abadleh, M., Schollmeyer, D., and Laufer, S., J. Med. Chem., 2007, vol. 50, p. 1213. https://doi.org/10.1021/jm061097o

    Article  CAS  PubMed  Google Scholar 

  91. Balasubramaniyan, V. and Argade, N.P., Synth. Commun., 1989, vol. 19, p. 3103. https://doi.org/10.1080/00397918908052708

    Article  CAS  Google Scholar 

  92. Huang, L.J., Hsieh, M.C., Teng, C.M., Lee, K.H., and Kuo, S.C., Bioorg. Med. Chem., 1998, vol. 6, p. 1657. https://doi.org/10.1016/S0968-0896(98)00141-2

    Article  CAS  PubMed  Google Scholar 

  93. Hellal, M. and Cuny, G.D., J. Org. Chem., 2010, vol. 75, p. 3465. https://doi.org/10.1021/jo1003339

    Article  CAS  PubMed  Google Scholar 

  94. Hellal, M. and Cuny, G.D., Org. Lett., 2010, vol. 12, p. 4628. https://doi.org/10.1021/ol101890t

    Article  CAS  PubMed  Google Scholar 

  95. González-Vera, J.A., Fueyo-Gonzalez, F., Alkorta, I., Peyressatre, M., Morris, M.C., and Herranz, R., Chem. Commun., 2016, vol. 52, p. 9652. https://doi.org/10.1039/c6cc04566a

    Article  Google Scholar 

  96. Tawada, H., Natsugari, H., Ishikawa, E., Sugiyama, Y., Ikeda, H., and Meguro, K., Chem. Pharm. Bull., 1995, vol. 43, p. 616. https://doi.org/10.1248/cpb.43.616

    Article  CAS  Google Scholar 

  97. Wang, L., Xie, S., Ma, L.J., Chen, Y., and Lu, W., Bioorg. Med. Chem., 2015, vol. 23, p. 1950. https://doi.org/10.1016/j.bmc.2015.03.031

    Article  CAS  PubMed  Google Scholar 

  98. Barile, E., De, S.K., Feng, Y.M., Chen, V., Yang, L., Ronai, Z., and Pellecchia, M., Chem. Biol. Drug. Des., 2013, vol. 82, p. 520. https://doi.org/10.1111/cbdd.12177

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  99. Robl, J.A., Synthesis, 1991, vol. 1, p. 56. https://doi.org/10.1055/s-1991-26379

    Article  Google Scholar 

  100. Yu, S.B., Huang, Q.Q., Luo, Y., and Lu, W., J. Org. Chem., 2012, vol. 77, p. 713. https://doi.org/10.1021/jo201974f

    Article  CAS  PubMed  Google Scholar 

  101. Yadav, J.S., Reddy, E.J., Madhavi, G., and Ramalingam, T., Heterocycl. Commun., 2000, vol. 6, p. 403. https://doi.org/10.1515/HC.2000.6.5.403

    Article  CAS  Google Scholar 

  102. Hewawasam, P., Fan, W.H., Cook, D.A., Newberry, K.S., Boissard, C.G., Gribkoff, V.K., Starrett, J., and Lodge, N.J., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 4479. https://doi.org/10.1016/j.bmcl.2004.06.051

    Article  CAS  PubMed  Google Scholar 

  103. Boy, K.M., Guernon, J.M., Sit, S.Y., Xie, K., Hewawasam, P., Boissard, C.G., Dworetzky, S.I., Natale, J., Gribkoff, V.K., Lodge, N., and Starrett, J.E., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 5089. https://doi.org/10.1016/j.bmcl.2004.07.080

    Article  CAS  PubMed  Google Scholar 

  104. Ribeiro, N., Tabaka, H., Peluso, J., Fetzer, L., Nebigil, C., Dumont, S., Muller, C.D., and Desaubry, L., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 5523. https://doi.org/10.1016/j.bmcl.2007.08.036

    Article  CAS  PubMed  Google Scholar 

  105. Prezent, M.A. and Dorokhov, V.A., Russ. Chem. Bull., 2003, vol. 52, p. 2454. https://doi.org/10.1023/B:Rucb.0000012369.78621.36

    Article  CAS  Google Scholar 

  106. Hashim, S.R. and Reddy, P.T., Indian J. Chem. B, 2001, vol. 40, p. 357.

    Google Scholar 

  107. Ruzi, R.H.G.L., Ma, J.Y., Yuan, X.A., Wang, W.L., Wang, S.S., Zhang, M.L., Dai, J., Xie, J., and Zhu, C.J., Chem. Eur. J., 2019, vol. 25, p. 12724. https://doi.org/10.1002/chem.201903816

    Article  CAS  PubMed  Google Scholar 

  108. Li, X.Y., Huo, X., Li, J.P., She, X.G., and Pan, X.F., Chin. J. Chem., 2009, vol. 27, p. 1379. https://doi.org/10.1002/cjoc.200990230

    Article  CAS  Google Scholar 

  109. Rehwald, M., Gewald, K., Lankau, H.J., and Unverferth, K., Heterocycles, 1997, vol. 45, p. 483. https://doi.org/10.3987/COM-96-7700

    Article  CAS  Google Scholar 

  110. Cheng, P., Zhang, Q., Ma, Y.B., Jiang, Z.Y., Zhang, X.M., Zhang, F.X., and Chen, J.J., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 3787. https://doi.org/10.1016/j.bmcl.2008.05.065

    Article  CAS  PubMed  Google Scholar 

  111. Esteve, M.E. and Gaozza, C.H., J. Heterocycl. Chem., 1981, vol. 18, p. 1061. https://doi.org/10.1002/jhet.5570180542

    Article  CAS  Google Scholar 

  112. Petersen, J.B. and Lakowitz, K.H., Acta Chem. Scand., 1969, vol. 23, p. 971. https://doi.org/10.3891/acta.chem.scand.23-0971

    Article  CAS  PubMed  Google Scholar 

  113. Sokolova, M.S., Lavrikova, T.I., and Gornostaev, L.M., Russ. J. Org. Chem., 2007, vol. 43, p. 625. https://doi.org/10.1134/S1070428007040252

    Article  CAS  Google Scholar 

  114. Kumar, S., Luxami, V., and Kumar, A., Org. Lett., 2008, vol. 10, p. 5549. https://doi.org/10.1021/ol802352j

    Article  CAS  PubMed  Google Scholar 

  115. Qian, W.Y., Wang, H., and Allen, J., Angew Chem., Int. Ed., 2013, vol. 52, p. 10992. https://doi.org/10.1002/anie.201305970

    Article  CAS  Google Scholar 

  116. He, B., Dai, J., Zherebetskyy, D., Chen, T.L., Zhang, B.A., Teat, S.J., Zhang, Q.C., Wang, L.W., and Liu, Y., Chem. Sci., 2015, vol. 6, p. 3180. https://doi.org/10.1039/c5sc00304k

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  117. Kumar, A., Vanita, V., Walia, A., and Kumar, S., Sens. Actuators B Chem., 2013, vol. 177, p. 904. https://doi.org/10.1016/j.snb.2012.11.093

    Article  CAS  Google Scholar 

  118. Kumar, A. and Kumar, S., Tetrahedron Lett., 2012, vol. 53, p. 2030. https://doi.org/10.1016/j.tetlet.2012.01.134

    Article  CAS  Google Scholar 

  119. Lv, D.J., Cui, J., Wang, Y.F., Zhu, G.H., Zhang, M.J., and Li, X.J., RSC Adv., 2017, vol. 7, p. 33494. https://doi.org/10.1039/c7ra04024e

    Article  CAS  Google Scholar 

  120. Elizbarashvili, E.N., Lagvilava, I.V., and Samsoniya, S.A., Chem. Heterocycl. Compd., 2005, vol. 41, p. 1868. https://doi.org/10.1021/ja305890c

    Article  CAS  Google Scholar 

  121. He, B., Pun, A.B., Klivansky, L.M., McGough, A.M., Ye, Y.F., Zhu, J.F., Guo, J.H., Teat, S.J., and Liu, Y., Chem Mater. 2014, vol. 26, p. 3920. https://doi.org/10.1021/cm5018272

  122. Gewald, K., Rehwald, M., Muller, H., and Bellmann, P., Liebigs Ann., 1995, vol. 1995, p. 787. https://doi.org/10.1002/jlac.1995199505115

    Article  Google Scholar 

  123. Goncharov, D.S., Kostuchenko, A.S., and Fisyuk, A.S., Chem. Heterocycl. Compd., 2009, vol. 45, p. 793. https://doi.org/10.1007/s10593-009-0358-8

    Article  CAS  Google Scholar 

  124. Fisyuk, A.S., Kulakov, I.V., Goncharov, D.S., Nikitina, O.S., Bogza, Y.P., and Shatsauskas, A.L., Chem. Heterocycl. Compd., 2014, vol. 50, p. 217. https://doi.org/10.1007/s10593-014-1464-9

    Article  CAS  Google Scholar 

  125. Kulakov, I.V., Matsukevich, M.V., Shulgau, Z.T., Sergazy, Sh., Seilkhanov, T.M., Puzari, A., and Fisyuk, A.S., Chem. Heterocycl. Compd., 2015, vol. 51, p. 991. https://doi.org/10.1007/s10593-016-1809-7

    Article  CAS  Google Scholar 

  126. Kulakov, I.V., Palamarchuk, I.V., Shulgau, Z.T., Seilkhanov, T.M., Gatilov, Y.V., and Fisyuk, A.S., J. Mol. Struct., 2018, vol. 1166, p. 262. https://doi.org/10.1016/j.molstruc.2018.04.036

    Article  CAS  Google Scholar 

  127. Shatsauskas, A.L., Abramov, A.A., Chernenko, S.A., Kostyuchenko, A.S., and Fisyuk, A.S., Synthesis, 2020, vol. 52, p. 227. https://doi.org/10.1055/s-0039-1690231

    Article  CAS  Google Scholar 

  128. Kulakov, I.V., Shatsauskas, A.L., Matsukevich, M.V., Palamarchuk, I.V., Seilkhanov, T.M., Gatilov, Y.V., and Fisyuk, A.S., Synthesis, 2017, vol. 49, p. 3700. https://doi.org/10.1055/s-0036-1590470

    Article  CAS  Google Scholar 

  129. Kulakov, I.V., Matsukevich, M.V., Levin, M.L., Palamarchuk, I.V., Seilkhanov, T.M., and Fisyuk, A.S., Synlett, 2018, vol. 29, p. 1741. https://doi.org/10.1055/s-0037-1610445

    Article  CAS  Google Scholar 

  130. Shatsauskas, A.L., Saibulina, E.R., Gatilov, Y.V., Kostyuchenko, A.S., and Fisyuk, A.S., Chem. Heterocycl. Compd., 2019, vol. 55, p. 1080. https://doi.org/10.1007/s10593-019-02581-8

    Article  CAS  Google Scholar 

  131. Fisyuk, A.S., Bogza, Y.P., Poendaev, N.V., and Goncharov, D.S., Chem. Heterocycl. Compd., 2010, vol. 46, p. 844. https://doi.org/10.1007/s10593-010-0592-0

    Article  CAS  Google Scholar 

  132. Goncharov, D.S., Kulakov, I.V., and Fisyuk, A.S., Chem. Heterocycl. Compd., 2017, vol. 53, p. 1335. https://doi.org/10.1007/s10593-018-2215-0

    Article  CAS  Google Scholar 

  133. Goncharov, D.S., Garkushenko, A.K., Savelieva, A.P., and Fisyuk, A.S., Arkivoc, 2015, vol. 5, p. 176. https://doi.org/10.3998/ark.5550190.p009.126

    Article  CAS  Google Scholar 

  134. Hommes, P., Berlin, S., and Reissig, H.U., Synthesis, 2013, vol. 45, p. 3288. https://doi.org/10.1055/s-0033-1338548

    Article  CAS  Google Scholar 

  135. Unger, L., Accorsi, M., Eidamshaus, C., Reich, D., Zimmer, R., and Reissig, H.U., Synthesis, 2018, vol. 50, p. 4071. https://doi.org/10.1055/s-0037-1609576

    Article  CAS  Google Scholar 

  136. Eidamshaus, C. and Reissig, H.-U., Eur. J. Org. Chem., 2011, p. 6056. https://doi.org/10.1002/ejoc.201100681

  137. Hommes, P., Jungk, P., and Reissig, H.-U., Synlett, 2011, p. 2311. https://doi.org/10.1055/s-0030-1260304

  138. Hommes, P., Fischer, C., Lindner, C., Zipse, H., and Reissig, H.-U., Angew. Chem., Int. Ed., 2014, vol. 53, p. 7647. https://doi.org/10.1002/anie.201403403

    Article  CAS  Google Scholar 

  139. Dash, J. and Reissig, H.-U., Chem. Eur. J., 2009, vol. 15, p. 6811. https://doi.org/10.1002/chem.200900939

    Article  CAS  PubMed  Google Scholar 

  140. Fyssiuk, A.S., Vorontsova, M.A., and Sagitullin, R.S., Mendeleev Commun., 1993, vol. 3, p. 249. https://doi.org/10.1070/MC1993v003n06ABEH000315

    Article  Google Scholar 

  141. Fisyuk, A.S., Vorontsova, M.A., and Ivanov, S.A., Chem. Heterocycl. Compd., 1994, vol. 30, p. 709. https://doi.org/10.1007/BF01166313

    Article  Google Scholar 

  142. Fisyuk, A.S. and Vorontsova, M.A., Chem. Heterocycl. Compd., 1998, vol. 34, p. 195. https://doi.org/10.1007/BF02315183

    Article  CAS  Google Scholar 

  143. Fisyuk, A.S. and Poendaev, N.V., Molecules, 2002, vol. 7, p. 119. https://doi.org/10.3390/70200119

    Article  CAS  PubMed Central  Google Scholar 

  144. Fissyuk, A.S., Vorontsova, M.A., and Temnikov, D.V., Tetrahedron Lett., 1996, vol. 37, p. 5203. https://doi.org/10.1016/0040-4039(96)01051-9

    Article  CAS  Google Scholar 

  145. Fisyuk, A.S., Berdovich, L.V., Temnlkov, D.V., and Knyaz’kova, L.N., Chem. Heterocycl. Compd., 1997, vol. 33, p. 805. https://doi.org/10.1007/BF02253030

    Article  CAS  Google Scholar 

  146. Fisyuk, A.S. and Vorontsova, M.A., Chem. Heterocycl. Compd., 1998, vol. 34, p. 65. https://doi.org/10.1007/BF02290614

    Article  CAS  Google Scholar 

  147. Fisyuk, A.S. and Poendaev, N.V., Molecules, 2002, vol. 7, p. 124. https://doi.org/10.3390/70200124

    Article  CAS  PubMed Central  Google Scholar 

  148. Chen, Q.-B., Xin, X.-L., Aisa, H.A., Phytochem. Lett., 2017, vol. 19, p. 168. https://doi.org/10.1016/j.phytol.2016.12.024

    Article  CAS  Google Scholar 

  149. Fisyuk, A.S. and Poendaev, N.V., Chem. Heterocycl. Compd., 2003, vol. 39, p. 895. https://doi.org/10.1023/A:1026146421293

    Article  CAS  Google Scholar 

  150. Fisyuk, A.S., Poendaev, N.V., and Bundel’, Yu.G., Mendeleev Commun., 1998, vol. 8, p. 12. https://doi.org/10.1070/MC1998v008n01ABEH000877

    Article  Google Scholar 

  151. Fisyuk, A.S., Poendaev, N.V., and Bundel’, Yu.G., Chem. Heterocycl. Compd., 1998, vol. 34, p. 258. https://doi.org/10.1007/BF02315198

    Article  CAS  Google Scholar 

  152. Fisyuk, A.S. and Poendaev, N.V., Chem. Heterocycl. Compd., 2003, vol. 39, p. 891. https://doi.org/10.1023/A:1026194204454

    Article  CAS  Google Scholar 

Download references

Funding

The review of the winners of the Ekspansiya Competition of the Russian Foundation for Basic Research 2019 (project no. 19-13-50277).

Author information

Authors and Affiliations

  1. Dostoevskii Omsk State University, 644077, Omsk, Russia

    A. S. Fisyuk & D. S. Goncharov

  2. Omsk State Technical University, 644050, Omsk, Russia

    A. S. Fisyuk & A. S. Kostyuchenko

Authors
  1. A. S. Fisyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. S. Kostyuchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. S. Goncharov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. S. Fisyuk.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fisyuk, A.S., Kostyuchenko, A.S. & Goncharov, D.S. Camps Reaction and Related Cyclizations. Russ J Org Chem 56, 1863–1892 (2020). https://doi.org/10.1134/S1070428020110019

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020110019

Keywords:

Search

Navigation