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Diazapyrenes. (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Published data on methods for the synthesis of isomeric diazapyrenes and their properties are reviewed.

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REFERENCES

  1. A. J. Blacker,J. Jazwinski,J.-M. Lehn, andF. X. Wilhels, J. Chem. Soc., Chem. Commun., 1035 (1986).

  2. J. Blacker,J. Jazwinski, andJ.-M. Lehn, US Patent 4925937; Chem. Abstr., 110, 75468 (1990).

    Google Scholar 

  3. H. Ikeda,K. Fuji, andK. Tanaka, Bioorg. Med. Chem. Lett., 6, 101 (1996).

    Google Scholar 

  4. A. Okamoto,T. Nakamura,K. Yoshida,K. Nakatani, andJ. Saito, Org. Lett., 21, 3249 (2000).

    Google Scholar 

  5. H.-C. Becker andB. Norden, J. Am. Chem. Soc., 119, 5798 (1997).

    Google Scholar 

  6. H.-C. Becker,A. Broo, andB. Norden, J. Phys. Chem., 101, 8853 (1997).

    Google Scholar 

  7. A. M. Brun andA. Harriman, J. Am. Chem. Soc., 113, 8153 (1991).

    Google Scholar 

  8. A. M. Brun andA. Harriman, J. Am. Chem. Soc., 114, 3656 (1992).

    Google Scholar 

  9. A. D. Andricopolo,L. A. Muller,V. C. Filho,G.-N. R. J. Cani, andR. A. Yunes, Farmaco, 55, 319; Chem. Abstr., 133, 217586 (2000).

    Google Scholar 

  10. H. E. Katz,J. Johnson,A. J. Lovinger, andW. Li, J. Am. Chem. Soc., 122, 7787 (2000).

    Google Scholar 

  11. S. Alp,S. Erten,C. Karapire,B. Koz,A. O. Doroshenko, andS. Icli, J. Photochem. Photobiol., A, 135, 103; Chem. Abstr., 133, 259160 (2000).

    Google Scholar 

  12. K. Kitamura,G. Matsushita, andT. Sato, Jpn. Patent 191, 937; Chem. Abstr., 133, 90774 (2000).

    Google Scholar 

  13. N. Leventis,I. A. Elder,D. R. Rolison,M. L. Anderson, andC. I. Merzbacher, Chem. Mater., 11, 2837 (1999); Chem. Abstr., 131, 337552 (1999).

    Google Scholar 

  14. I. Piantanida,V. Tomisic, andM. Zinic, J. Chem. Soc., Perkin Trans. 2, 375 (2000).

  15. B. S. Palm,I. Piantanida,M. Zinic, andH.-J. Schneider, J. Chem. Soc., Perkin Trans. 2, 385 (2000).

  16. S. Roknic,L. Glavas-Obrovac,I. Karner,I. Piantanida,M. Zinic, andK. Pavelic, Chemotherapy, 46, 143 (2000).

    Google Scholar 

  17. I. Piantanida,B. S. Palm,M. Zinic, andH.-J. Schneider, J. Chem. Soc., Perkin Trans. 2, 1808 (2001).

  18. I. Steiner-Biocic,L. Glavas-Obrovac,I. Karner,I. Piantanida,M. Zinic,K. Pavelic, andJ. Pavelic, Anticancer Res., 16, 3705 (1996).

    Google Scholar 

  19. V. Balzani,A. Credi,S. J. Langford,F. M. Raymo,J. F. Stoddart, andM. Venturi, J. Am. Chem. Soc., 122, 3542 (2000).

    Google Scholar 

  20. R. Cahn andO. Dermer, Introduction to Chemical Nomenclature [Russian translation], Khimiya, Moscow (1983), p. 116.

  21. A. E. S. Fairfull,D. A. Peak,W. F. Short, andT. I. Watkins, J. Chem. Soc., 4700 (1952).

  22. W. L. Mosby, J. Org. Chem., 22, 671 (1957).

    Google Scholar 

  23. R. Kiralj,B. Kojic-Prodic,I. Piantanida, andM. Zinic, Acta Crystallogr., B55, 55 (1999).

    Google Scholar 

  24. G. S. Matvelashvili,S. F. Belevskii,O. Ya. Fedotova, andG. S. Kolesnikov, Khim. Geterotsikl. Soedin., 1044 (1969).

  25. G. M. Badger andW. F. H. Sasse, J. Chem. Soc., 4 (1957).

  26. R. F. Robbins, J. Chem. Soc., 2553 (1960).

  27. Y. Mugnier andE. Laviron, Bull. Soc. Chim. France, 39 (1978).

  28. J. Kenner andW. V. Stubbing, J. Chem. Soc., 593 (1921).

  29. C. W. Muth,J. R. Elkins,M. L. DeMatte, andS. T. Chiang, J. Org. Chem., 32, 1106 (1967).

    Google Scholar 

  30. G. I. Migachev,A. M. Terent'ev, andV. I. Lisoded, Khim. Geterotsikl. Soedin., 1672 (1979).

  31. G. H. Christie andJ. Kenner, J. Chem. Soc., 470 (1926).

  32. G. I. Migachev,A. M. Andrievskii, andN. S. Dokunikhin, Khim. Geterotsikl. Soedin., 1699 (1975).

  33. G. I. Migachev,N. G. Grekhov, andA. M. Terent'ev, Khim. Geterotsikl. Soedin., 388 (1981).

  34. B. Coffin andR. F. Robbins, J. Chem. Soc., 3379 (1965).

  35. G. I. Migachev,L. V. Eremenko,Ya. G. Urman,A. Kh. Bulai, andK. M. Dyumaev, Zh. Org. Khim., 15, 1491 (1979).

    Google Scholar 

  36. W. Jenny andH. Holzrichter, Chimia, 22, 247 (1968).

    Google Scholar 

  37. W. Jenny andH. Holzrichter, Chimia, 21, 509 (1967).

    Google Scholar 

  38. E. F. Lier,S. Hunig, andH. Quasi, Angew. Chem., 80, 799 (1968).

    Google Scholar 

  39. S. Hunig,J. Gross,E. F. Lier, andH. Quasi, Liebigs Ann. Chem., 339 (1973).

  40. P. J. Slang,D. H. Cao,S. Sailo, andA. M. Arif, J. Am. Chem. Soc., 117, 6273 (1995).

    Google Scholar 

  41. C. Soliriou-Levenlis,Z. Mao, andA.-M. M. Rawashdeh, J. Org. Chem., 65, 6017 (2000).

    Google Scholar 

  42. J. Jazwinski,A. J. Blacker,J.-M. Lehn,M. Cesario,J. Guilhem, andC. Pascard, Tetrahedron Lett., 28, 6057 (1987).

    Google Scholar 

  43. K. Kishikawa,C. Iwashima,S. Kohmolo,K. Yamaguchi, andM. Yamamoto, J. Chem. Soc. Perkin Trans. 1, 2217 (2000).

  44. H.-D. Becker,B. W. Skellon, andA. H. White, Aust. J. Chem., 40, 625 (1987).

    Google Scholar 

  45. T. Kamata andN. Wasada, Jpn. Patent 11322, 747; Chem. Abstr., 131, 337016 (1999).

    Google Scholar 

  46. T. Kamala andN. Wasada, Synthesis, 967 (1990).

  47. C. Soliriou-Levenlis andZ. Mao, J. Heterocycl. Chem., 37, 1665 (2000).

    Google Scholar 

  48. M. Dufour,N. P. Buu-Hoi, andP. Jacquignon, J. Chem. Soc. C, 1415 (1967).

  49. A. Edel,P. A. Marnol, andJ. P. Sauvage, Tetrahedron Lett., 26, 727 (1985).

    Google Scholar 

  50. R. Neidlein andZ. Behzadi, Chem. Ztg., 102, 199 (1978).

    Google Scholar 

  51. R. Neidlein andZ. Behzadi, Chem. Ztg., 102, 150 (1978).

    Google Scholar 

  52. K.-D. Franz, Chemistry Lett., 221 (1979).

  53. A. F. Pozharskii andV. V. Dal'nikovskaya, Usp. Khim., 50, 1559 (1981).

    Google Scholar 

  54. R. M. Claramunl,J. Dolor, andJ. Elguero, An. Quim., 91, 151 (1995).

    Google Scholar 

  55. I. V. Borovlev,A. V. Aksenov, andA. F. Pozharskii, Khim. Geterotsikl. Soedin., 1579 (1997).

  56. I. V. Borovlev,O. P. Demidov, andA. F. Pozharskii, Khim. Geterotsikl. Soedin., 1109 (2002).

  57. O. Dimrot andH. Roos, Liebigs Ann. Chem., 456, 177 (1927).

    Google Scholar 

  58. F. Gerson, Helv. Chim. Acta, 47, 1484 (1964).

    Google Scholar 

  59. I. V. Borovlev,O. P. Demidov, andA. F. Pozharskii, Khim. Geterotsikl. Soedin., 278 (2002).

  60. I. V. Borovlev,O. P. Demidov,A. V. Chernyshev, andA. F. Pozharskii, Izv. Akad. Nauk. Ser. Khim., 132 (2002).

  61. O. P. Demidov,I. V. Borovlev, andA. F. Pozharskii, Khim. Geterotsikl. Soedin., 133 (2001).

  62. O. P. Demidov,I. V. Borovlev, andA. F. Pozharskii, Khim. Geterotsikl. Soedin., 1136 (2001).

  63. I. V. Borovlev,O. P. Demidov, andA. F. Pozharskii, Izv. Akad. Nauk. Ser. Khim., 794 (2002).

  64. I. V. Borovlev,O. P. Demidov, andA. F. Pozharskii, Khim. Geterotsikl. Soedin., 1247 (2002).

  65. I. V. Borovlev andA. F. Pozharskii, Khim. Geterotsikl. Soedin., 833 (1978).

  66. I. V. Borovlev andA. F. Pozharskii, USSR Inventor's Certificate 563417; Byull. Izobr., No. 24 (1977).

  67. I. V. Borovlev andA. F. Pozharskii, USSR Inventor's Certificate 596581; Byull. Izobr., No. 9 (1978).

  68. I. V. Borovlev andA. F. Pozharskii, Khim. Geterotsikl. Soedin., 1688 (1975).

  69. L. A. Summers andV. A. Pickles, Chem. Ind., 619 (1967).

  70. A. L. Black,L. A. Summers, andV. A. Pickles, Chem. Ind., 1836 (1967).

  71. I. C. Calder andW. H. F. Sasse, Aust. J. Chem., 21, 2951 (1968).

    Google Scholar 

  72. A. K. Sheinkman,M. M. Mestechkin,A. P. Kucherenko,V. V. Artemova,V. N. Poltavets, andYu. B. Vysotskii, Khim. Geterotsikl. Soedin., 537 (1974).

  73. E. W. Thulstrup,J. W. Downing, andJ. Michl, Chem. Phys., 23, 307 (1977).

    Google Scholar 

  74. E. W. Thulstrup andJ. Michl, J. Am. Chem. Soc., 104, 5594 (1982).

    Google Scholar 

  75. S. A. Tacker,H. Darmodjo,W. E. Acree,M. Zander, andE. C. Meisler,Appl. Spectrosc., 46, 1630 (1992).

    Google Scholar 

  76. M. Gawlak andR. F. Robbins, J. Chem. Soc., 5135 (1964).

  77. B. E. Zaitsev,G. I. Migachev,O. P. Koval'chukova, andV. V. Matyushenko, Khim. Geterotsikl. Soedin., 94 (1993).

  78. W. F. H. Sasse, in: A. Albert,G. M. Badger, andC. W. Shoppee (editors), Current Trends in Heterocyclic Chemistry, London, Butterworths, 1958, p. 83.

    Google Scholar 

  79. A. T. Hawkinson andA. A. Elston, US Patent 2371691; Chem. Abstr., 39, 4336 (1945).

    Google Scholar 

  80. L. P. Walls, J. Chem. Soc., 1405 (1935).

  81. S. Hunig andJ. Gross, Tetrahedron Lett., 2599 (1968).

  82. A. J. Blacker,J. Jazwinski, andJ.-M. Lehn, Helv. Chim. Acta, 70, 1 (1987).

    Google Scholar 

  83. J. Bruhin andF. Gerson, Helv. Chim. Acta, 58, 2422 (1975).

    Google Scholar 

  84. V. Podany,A. Vashalkova,S. Miertus, andL. Bahna, Neoplasma, 22, 5 (1975).

    Google Scholar 

  85. V. Podany,A. Vashalkova, andL. Bahna, Neoplasma, 23, 617 (1976).

    Google Scholar 

  86. D. Gosztola,M. P. Niemczyk,W. Svec,A. S. Lukas, andM. R. Wasielewski, J. Phys. Chem. A, 104, 6545 (2000).

    Google Scholar 

  87. P. R. Ashton,S. E. Boyd,A. Brindle,S. J. Langford,S. Menzer,L. Perez-Garcia,J. A. Preece,M. Raymo,N. Spencer,S. J. Fraser,A. J. P. White, andD. J. Williams, New J. Chem., 23, 587 (1999).

    Google Scholar 

  88. A. F. Pozharskii, Theoretical Principles of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985), p. 212.

  89. J. W. Bunting, Adv. Heterocycl. Chem., 25, 1 (1979).

    Google Scholar 

  90. L. F. Fieser andE. B. Hershberg, J. Am. Chem. Soc., 62, 1640 (1940).

    Google Scholar 

  91. G. I. Migachev andA. M. Terent'ev, Khim. Geterotsikl. Soedin., 394 (1981).

  92. B. E. Zaitsev,G. I. Migachev,L. V. Sakhashchik,Yu. P. Kobzev,D. N. Gromov,Z. K. Odinets,A. M. Terent'ev, andK. M. Dyumaev, USSR Inventor's Certificate 1388408; Byull. Izobr., No. 14, 117 (1988).

  93. A. Credi,V. Balzani,S. J. Langford,M. Montalti,F. M. Raymo, andJ. F. Stoddart, New J. Chem., 22, 1061 (1998).

    Google Scholar 

  94. R. Ballardini,V. Balzani,A. Credi,M. T. Gandolfi,S. J. Langford,S. Menzer,L. Prodi,J. F. Stoddart,M. Venturi, andD. J. Williams, Angew. Chem., Int. Ed. Engl., 35, 978 (1996).

    Google Scholar 

  95. N. N. Barashkov,I. V. Korotkova, andT. V. Sakhno, J. Luminesc., 87-89, 794 (2000).

    Google Scholar 

  96. E. Waldhoer,M. M. Zulu,S. Zalis, andW. Kaim, J. Chem. Soc., Perkin Trans. 2, 1197 (1996).

  97. A. J. Blake,N. R. Champness,A. N. Khlobystov,D. A. Lemenovskii,W.-S. Li, andM. Schroeder, J. Chem. Soc., Chem. Commun., 15, 1339 (1997).

    Google Scholar 

  98. A. J. Blake,G. Baum,N. R. Champness,S. S. M. Chung,P. A. Cooke,D. Fenske,A. N. Khlobystov,D. A. Lemenovskii,W.-S. Li, andM. Schroeder, J. Chem. Soc., Dalton Trans., 4285 (2000).

  99. T. Ito,T. Yamaguchi, andC. P. Kubiak, Macromol. Symposia, 156, 269 (2000).

    Google Scholar 

  100. G.-H. Lee,L. D. Ciana, andA. Haim, J. Am. Chem. Soc., 111, 2535 (1989).

    Google Scholar 

  101. P. J. Stang,B. Olenyuk,J. Fan, andA. M. Arif, Organometallics, 15, 904 (1996).

    Google Scholar 

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Borovlev, I.V., Demidov, O.P. Diazapyrenes. (Review). Chemistry of Heterocyclic Compounds 39, 1417–1442 (2003). https://doi.org/10.1023/B:COHC.0000014408.07085.75

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