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Sulfated polyborate catalyzed Kindler reaction: a rapid, efficient, and green protocol

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Abstract

A rapid, green, and efficient one-pot, three-component Kindler reaction was developed using a sulfated polyborate catalyst. The method described the reaction of aldehydes, amines/ammonium acetate, and sulfur for the synthesis of thioamides using sulfated polyborate under a solvent free condition at 100 °C. The key features of the present protocol are high yields, short reaction time, easy workup, and recyclability of a catalyst which gives economical as well as ecological rewards. The present method also has an ability to tolerate a variety of functional groups.

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References

  1. Kindler K (1923) Justus Liebigs Ann Chem 431:187

    Article  CAS  Google Scholar 

  2. Suzuki Y, Iwata M, Yazaki R, Kumagai N, Shibasaki M (2012) J Org Chem 77:4496

    Article  CAS  Google Scholar 

  3. Murai T, Hori F, Maruyama T (2011) Org Lett 13:1718

    Article  CAS  Google Scholar 

  4. Gopinath P, Watanabe T, Shibasaki M (2012) J Org Chem 77:9260

    Article  CAS  Google Scholar 

  5. Shekarchi M, Pirali-Hamedani M, Navidpour L, Adib N, Shafiee A (2008) J Iran Chem Soc 5:150

    Article  CAS  Google Scholar 

  6. Nadeem S, Bolte M, Ahmad S, Fazeelat T, Tirmizi SA, Ahmed S, Rauf MK, Sattar SA, Siddiq S, Hameed A, Haider SZ Fazeelat T, Tirmizi SA, Ahmed S, Rauf MK, Sattar SA, Siddiq S, Hameed A, Haider SZ (2010) Inorg Chim Acta 363:3261

  7. Kuneš J, Balšánek V, Pour M, Waisser K, Kaustová J (2002) Farm 57:777

    Article  Google Scholar 

  8. Chernovyants MS, Aleshina NV (2012) J Anal Chem 67:214

    Article  CAS  Google Scholar 

  9. Kulandasamy R, Adhikari AV, Stables JP (2010) Bull Korean Chem Soc 31:3318

    Article  CAS  Google Scholar 

  10. Chernov’yants MS, Dolinkin AO (2010) J Struct Chem 51:1176

  11. Brunhofer G, Studenik C, Ecker GF, Erker T (2011) Eur J Pharm Sci 42:37

    Article  CAS  Google Scholar 

  12. Gibinski K (1981) Curr Med Res Opin 7:516

    Article  CAS  Google Scholar 

  13. Hu W-P, Yu H-S, Chen Y-R, Tsai Y-M, Chen Y-K, Liao C-C, Chang S-N, Wang J-J (2008) Bioorg Med Chem 16:5295

    Article  CAS  Google Scholar 

  14. Showalter HDH, Johnson JL, Werbel LM, Leopold WR, Jackson RC, Elslager EF (1984) J Med Chem 27:255

    Article  Google Scholar 

  15. Stauffer SR, Coletta CJ, Tedesco R, Nishiguchi G, Carlson K, Sun J, Katzenellenbogen SB, Katzenellenbogen JA (2000) J Med Chem 43:4934

    Article  CAS  Google Scholar 

  16. Hisano T, Yabuta Y (1973) Chem Pharm Bull 21:511

    Article  CAS  Google Scholar 

  17. Kamisuki S, Mao Q, Abu-Elheiga L, Gu Z, Kugimiya A, Kwon Y, Choo HYP (2009) Chem Biol 16:882

    Article  CAS  Google Scholar 

  18. Martin S, Lenz EM, Keene W, Clench MR (2014) Anal Chem 86:11281

    Article  CAS  Google Scholar 

  19. Brown K, Cater DP, Cavalla JF, Green D, Newberry RA, Wilson AB (1974) J Med Chem 17:1177

    Article  CAS  Google Scholar 

  20. Becker MA, Kisicki J, Khosravan R, Wu J, Mulford D, Hunt B, Joseph-Ridge N (2004) Nucleotides Nucleic Acids 23:1111

    Article  CAS  Google Scholar 

  21. Quemard A, Laneelle G, Lacave C (1992) Antimicrob Agents Chemother 36:1316

    Article  CAS  Google Scholar 

  22. Wang F, Langley R, Gulten G, Dover LG, Besra GS, Jacobs WR, Sacchettini JC (2007) J Exp Med 204:73

    Article  CAS  Google Scholar 

  23. DeMello WC, Re RN (2009) Renin angiotensin system and cardiovascular disease. Springer, New York, p 1

  24. Raucher S, Klein P (1981) J Org Chem 46:3558

    Article  CAS  Google Scholar 

  25. Cava MP, Levinson MI (1985) Tetrahedron 41:5061

    Article  CAS  Google Scholar 

  26. Wojtkowski PW, Dolfini JE, Kocy O, Cimarusti CM (1975) J Am Chem Soc 97:5628

    Article  CAS  Google Scholar 

  27. Hirabayashi T, Inoune K, Yokota K, Ishii Y (1975) J Organomet Chem 92:139

    Article  CAS  Google Scholar 

  28. Ogata M, Matsumoto H (1978) Heterocycles 11:139

    Article  CAS  Google Scholar 

  29. Okamoto K, Yamamoto T, Kanbara T (2007) Synlett 2687

  30. Poupaert JH, Duarte S, Colacino E, Dover LG, Besra GS, Jacobs WR, Sacchettini JC (2004) Phosphorus. Sulfur Silicon Relat Elem 179:1959

    Article  CAS  Google Scholar 

  31. Agnimonhan FH, Ahoussi L, Kpoviessi SDS, Gbaguidi FA, Kapanda CN, Moudachirou M, Accrombessi GC (2014) Int J Biol Chem Sci 8:386

    Article  Google Scholar 

  32. Kul’ganek VV, Yanovskaya LA (1979) Bull Acad Sci USSR Div Chem Sci 28:2402

  33. Pathare SP, Chaudhari PS, Akamanchi KG (2012) Appl Catal A Gen 425–426:125

    Article  Google Scholar 

  34. Yin Z, Zheng B (2013) J Sulfur Chem 34:527

    Article  CAS  Google Scholar 

  35. Yin Z, Zheng B, Ai F (2013) Phosphorus. Sulfur Silicon Relat Elem 188:1412

    Article  CAS  Google Scholar 

  36. Khatri CK, Rekunge DS, Chaturbhuj GU (2016) New J Chem 40:10412

    Article  CAS  Google Scholar 

  37. Khatri CK, Satalkar VB, Chaturbhuj GU (2017) Tetrahedron Lett 58:694

    Article  CAS  Google Scholar 

  38. Indalkar KS, Khatri CK, Chaturbhuj GU (2017) J Chem Sci 129:141

    Article  CAS  Google Scholar 

  39. Rekunge DS, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:1240

    Article  CAS  Google Scholar 

  40. Matloubi Moghaddam F, Hojabri L, Dohendou M (2003) Synth Commun 33:4279

    Article  CAS  Google Scholar 

  41. Okuma K, Komiya Y, Ohta H (1988) Chem Lett 17:1145

    Article  Google Scholar 

  42. Otten PA, Van der Gen A (2010) Recl Trav Chim Pays Bas 113:499

    Article  Google Scholar 

  43. Fazylov SD, Nurkenov OA, Akhmetkarimova ZS, Zhienbaeva DR (2012) Russ J Gen Chem 82:781

    Article  CAS  Google Scholar 

  44. Gompper R, Schmidt RR (1965) Chem Ber 98:1385

    Article  CAS  Google Scholar 

  45. Kuliev AB, Kurbanov MM, Mamedov AG, Kuliev FA (1985) J Appl Chem USSR 58:139

    Google Scholar 

  46. Chabrier P, Renard SH, Smarzewska K (1950) Bull Soc Chim Fr 17:1167

    Google Scholar 

  47. Shibuya I, Honda K, Gama Y, Shimizu M (2002) Heterocycles 57:429

    Article  CAS  Google Scholar 

  48. Nguyen TB, Ermolenko L, Al-Mourabit A (2012) Org Lett 14:4274

    Article  CAS  Google Scholar 

  49. Pace V, Castoldi L, Monticelli S, Safranek S, Roller A, Langer T, Holzer W (2015) Chem Eur J 21:18966

    Article  CAS  Google Scholar 

  50. Smith DC, Lee SW, Fuchs PL (1994) J Org Chem 59:348

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are grateful to University Grants Commission, New Delhi, India for their financial supports.

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Correspondence to Ganesh U. Chaturbhuj.

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Khatri, C.K., Mali, A.S. & Chaturbhuj, G.U. Sulfated polyborate catalyzed Kindler reaction: a rapid, efficient, and green protocol. Monatsh Chem 148, 1463–1468 (2017). https://doi.org/10.1007/s00706-017-1944-6

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  • DOI: https://doi.org/10.1007/s00706-017-1944-6

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