A thioannulation approach to substituted thiophenes from morita-baylis-hillman acetates of acetylenic aldehydes

Journal of Organic Chemistry

Volumn 78, Issue 13, 2013, Pages 6495-6502

  Reddy, Chada Raji ^a   Valleti, Reddi Rani ^a   Reddy, Motatipally Damoder ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC SUBSTITUTION; DIHYDROQUINOLINE; METAL-FREE REACTIONS; MORITA-BAYLIS-HILLMAN; NEW PROTOCOL; SUBSTITUTED THIOPHENE;

RATE CONSTANTS; THIOPHENE;

ALDEHYDES;

ACETIC ACID DERIVATIVE; ALDEHYDE; CHROMENE DERIVATIVE; DIHYDROQUINOLINE DERIVATIVE; POTASSIUM; THIOPHENE DERIVATIVE;

ANNULATION REACTION; ARTICLE; ISOMERIZATION; SUBSTITUTION REACTION; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY;

ACETATES; ALDEHYDES; MOLECULAR STRUCTURE; THIOPHENES;

EID: 84880031564     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400567h     Document Type: Article

References (53)

1. Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles; Wiley-VCH: New York, 2003; Chapter 5, section 5.6.
2. Russell, R. K.; Press, J. B. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. W. F., Padwa, A., Eds.; Pergamon: New York, 1996; Vol. 2, p 6790.
3. Wu, C.; Decker, C. E. R.; Blok, N.; Bui, H.; You, T. J.; Wang, J.; Bourgoyne, A. R.; Knowles, V.; Berens, K. L.; Holland, G. W.; Brock, T. A.; Dixon, R. A. F. J. Med. Chem. 2004, 47, 1969
4. Dore, K.; Dubus, S.; Ho, H. A.; Levesque, I.; Brunette, M.; Corbeil, G.; Boissinot, M.; Boivin, G.; Bergeron, M. G.; Boudreau, D.; Leclerc, M. J. Am. Chem. Soc. 2004, 126, 4240
5. Bohlmann, F.; Zdero, C. Naturally Occuring Thiophenes. Chemistry of Heterocyclic Compounds; John Wiley and Sons Inc.: New York, 1985; Vol. 44, p 261.
6. Derridj, F.; Larbi, K. S.; Roger, J.; Djebbar, S.; Doucet, H. Tetrahedron 2012, 68, 7463
7. Wolf, J. J.; Wortmann, R. Adv. Phys. Org. Chem. 1999, 32, 121
8. Morrison, J. J.; Murray, M. M.; Li, X. C.; Holmes, A. B.; Morrati, S. C.; Friend, R. H.; Sirringhaus, H. Synth. Met. 1999, 102, 987
9. Li, X. C.; Sirringhaus, H.; Garrier, F.; Holmes, A. B.; Morrati, S. C.; Feeder, N.; Clegg, W.; Teat, S. J.; Friend, R. H. J. Am. Chem. Soc. 1998, 120, 2206
10. Kiani, M. S.; Mitchell, G. R. Synth. Met. 1992, 46, 293
11. Greenham, N. C.; Morratti, S. C.; Bradley, D. D. C.; Friend, R. Y.; Holmes, A. B. Nature (London) 1993, 365, 628
12. Bheeter, C. B.; Bera, J. K.; Doucet, H. J. Org. Chem. 2011, 76, 6407
13. Lethu, S.; Dubois, J. Eur. J. Org. Chem. 2011, 3920
14. Dolman, N. P.; More, J. C. A.; Alt, A.; Knauss, J. L.; Pentikainen, O. T.; Glasser, C. R.; Bleakman, D.; Mayer, M. L.; Collingridge, G. L.; Jane, D. E. J. Med. Chem. 2007, 50, 1558
15. Bayh, O.; Awad, H.; Mongin, F.; Hoarau, C.; Trécourt, F.; Quéquiner, F.; Marsais, F.; Blanco, F.; Abarca, B.; Ballesteros, R. Tetrahedron 2005, 61, 4779
16. Gewald, K. Angew. Chem. 1961, 73, 114
17. Revelant, G.; Dunand, S.; Hesse, S.; Kirsch, G. Synthesis 2011, 2935
18. Knorr, L. Ber. Dtsch. Chem. Ges. 1884, 17, 1635
19. Paal, C. Ber. Dtsch. Chem. Ges. 1885, 18, 367
20. Campaigne, E.; Foye, W. O. J. Org. Chem. 1952, 62, 1405
21. Minetto, G.; Raveglia, L. F.; Sega, A.; Taddei, M. Eur. J. Org. Chem. 2005, 5277
22. Swaroop, T. R.; Roopashree, R.; Ila, H.; Rangappa, K. S. Tetrahedron Lett. 2013, 54, 147
23. Liao, Q.; You, W.; Lou, Z.; Wen, L.; Xi, C. Tetrahedron Lett. 2013, 54, 1475
24. Mishra, P.; Maurya, H. K.; Kumar, B.; Tandon, V. K.; Ramc, V. J. Tetrahedron Lett. 2012, 53, 1056
25. Tang, J.; Zhao, X. RSC Adv. 2012, 2, 5488
26. Guilarte, V.; Fernandez-RodrIguez, M. A.; GarcIa-GarcIa, P.; Hernando, E.; Sanz, R. Org. Lett. 2011, 13, 5100
27. You, W.; Yan, Liao, Q.; Xi, C. Org. Lett. 2010, 12, 3930
28. Zhang, Y.; Bian, M.; Yao, W.; Gu, J.; Ma, C. Chem. Commun. 2009, 45, 4729
29. Thomae, D.; Perspicace, E.; Henryon, D.; Xu, Z.; Schneider, S.; Hesse, S.; Kirsch, G.; Seck, P. Tetrahedron 2009, 65, 10453
30. Teiber, M.; Muller, T. J. J. Chem. Commun. 2012, 48, 2080
31. Fang, Z.; Yuan, H.; Liu, Y.; Tong, Z.; Li, H.; Yang, J.; Barry, B.; Liu, J.; Liao, P.; Zhang, J.; Liu, Q.; Bi, X. Chem. Commun. 2012, 48, 8802
32. Jalani, H. B.; Pandya, A. N.; Pandya, D. H.; Sharma, J. A.; Sudarsanam, V.; Vasu, K. K. Tetrahedron Lett. 2012, 53, 6927
33. Nandi, G. C.; Samai, S.; Singh, M. S. J. Org. Chem. 2011, 76, 8009
34. Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 6480
35. Samuel, R.; Chandran, P.; Retnamma, S.; Sasikala, K. A.; Sreedevi, N. K.; Anabha, E. R.; Asokan, C. V. Tetrahedron 2008, 64, 5944
36. Wang, Y.; Dong, D.; Yang, Y.; Huang, J.; Ouyang, Y.; Liu, Q. Tetrahedron 2007, 63, 2724
37. Moghaddam, F. M.; Boinee, H. Z. Tetrahedron 2004, 60, 6085
38. Marshall, J. A.; DuBay, W. J. Synlett 1993, 209
39. Gabriele, B.; Salerno, G.; Fazio, A. Org. Lett. 2000, 2, 351
40. Gabriele, B.; Mancuso, R.; Salerno, G.; Larock, R. C. J. Org. Chem. 2012, 77, 7640
41. Gabriele, B.; Mancuso, R.; Veltri, L.; Maltese, V.; Salerno, G. J. Org. Chem. 2012, 77, 9905
42. Reddy, C. R.; Reddy, M. D.; Srikanth, B. Org. Biomol. Chem. 2012, 10, 4280
43. Reddy, C. R.; Kumaraswamy, P.; Reddy, M. D. Org. Biomol. Chem. 2012, 10, 9052
44. Reddy, C. R.; Reddy, M. D.; Srikanth, B.; Prasad, K. R. Org. Biomol. Chem. 2011, 9, 6027
45. Liu, Y.; Xu, D.; Xu, Z.; Zhang, Y. Heteroat. Chem. 2008, 19, 188
46. Cha, M. J.; Song, Y. S.; Lee, K. J. Bull. Korean Chem. Soc. 2006, 27, 1900
47. Xiao-Bo, X.; Jian, L.; Jian-Jian, Z.; Ya-Wen, W.; Yu, P. Org. Lett. 2013, 15, 550
48. Jiehao, C. C.; Craig, J. F. J. Am. Chem. Soc. 2003, 125, 8734
49. Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445
50. Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687
51. Gabriele, B.; Salerno, G.; Fazio, A. J. Org. Chem. 2003, 68, 7853
52. Katsiel, A. L.; Sharipova, A. N.; Fisyuk, A. S. Mendeleev Commun. 2008, 18, 169
53. Park, S. P.; Ahn, S. H.; Lee, K. J. Tetrahedron 2010, 66, 3490