An expedient synthesis of poly-substituted pyrroles from γ-ketonitriles via indium-mediated Barbier reaction strategy

Tetrahedron Letters

Volumn 50, Issue 41, 2009, Pages 5744-5747

  Kim, Sung Hwan ^a   Kim, Se Hee ^a   Lee, Ka Young ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Ketonitriles; Barbier reaction; Indium; Pyrroles

Indexed keywords

ACETIC ACID DERIVATIVE; CHLORIDE; DESYL CHLORIDE; ENAMINE; GAMMA KETONITRILE DERIVATIVE; INDIUM; KETONE DERIVATIVE; LACTONE DERIVATIVE; METHYL CYANOACETATE; NITRILE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; LACTONIZATION; POLYMERIZATION; SYNTHESIS;

EID: 68949214015     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.140     Document Type: Article

References (33)

1. For the general review on indium-mediated reactions, see:. Auge J., Lubin-Germain N., and Uziel J. Synthesis (2007) 1739-1764
2. Li C.-J., and Chan T.-H. Tetrahedron 55 (1999) 11149-11176
3. Pae A.N., and Cho Y.S. Curr. Org. Chem. 6 (2002) 715-737
4. For the indium-mediated Barbier type allylation of imine, acylimine, sulfonimine and related compounds, see:. Vilaivan T., Winotapan C., Banphavichit V., Shinada T., and Ohfune Y. J. Org. Chem. 70 (2005) 3464-3471
5. Schneider U., Chen I.-H., and Kobayashi S. Org. Lett. 10 (2008) 737-740
6. Kumar H.M.S., Anjaneyulu S., Reddy E.J., and Yadav J.S. Tetrahedron Lett. 41 (2000) 9311-9314
7. Piao X., Jung J.-K., and Kang H.-Y. Bull. Korean Chem. Soc. 28 (2007) 139-142
8. Ritson D.J., Cox R.J., and Berge J. Org. Biomol. Chem. 2 (2004) 1921-1933
9. Lu W., and Chan T.H. J. Org. Chem. 65 (2000) 8589-8594
10. Ranu B.C., and Das A. Tetrahedron Lett. 45 (2004) 6875-6877
11. Fujiwara N., and Yamamoto Y. Tetrahedron Lett. 39 (1998) 4729-4732
12. Fujiwara N., and Yamamoto Y. J. Org. Chem. 64 (1999) 4095-4101
13. Kim S.H., Lee H.S., Kim K.H., and Kim J.N. Tetrahedron Lett. 50 (2009) 1696-1698
14. For the synthesis and biological activities of pyrrole derivatives, see:. Fan H., Peng J., Hamann M.T., and Hu J.-F. Chem. Rev. 108 (2008) 264-287
15. Gupton J.T. Top. Heterocycl. Chem. 2 (2006) 53-92
16. Roy A.K., Pathak R., Yadav G.P., Maulik P.R., and Batra S. Synthesis (2006) 1021-1027
17. Singh V., Kanojiya S., and Batra S. Tetrahedron 62 (2006) 10100-10110
18. Bellina F., and Rossi R. Tetrahedron 62 (2006) 7213-7256
19. Knight D.W., and Sharland C.M. Synlett (2004) 119-121
20. Knight D.W., and Sharland C.M. Synlett (2003) 2258-2260
21. Foley L.H. Tetrahedron Lett. 35 (1994) 5989-5992
22. Lee H.S., Kim J.M., and Kim J.N. Tetrahedron Lett. 48 (2007) 4119-4122
23. Kim S.J., Kim H.S., Kim T.H., and Kim J.N. Bull. Korean Chem. Soc. 28 (2007) 1605-1608
24. Kim J.M., Lee S., Kim S.H., Lee H.S., and Kim J.N. Bull. Korean Chem. Soc. 29 (2008) 2215-2220 and further references cited therein
25. For the synthesis and biological activities of pyrrole-containing compounds, see:. Thasana N., Worayuthakarn R., Kradanrat P., Hohn E., Young L., and Ruchirawat S. J. Org. Chem. 72 (2007) 9379-9382
26. Su S., and Porco Jr. J.A. J. Am. Chem. Soc. 129 (2007) 7744-7745
27. Dhawan R., and Arndtsen B.A. J. Am. Chem. Soc. 126 (2004) 468-469
28. Pandey P.S., and Rao T.S. Bioorg. Med. Chem. Lett. 14 (2004) 129-131
29. 8 Compounds 1i and 1j were prepared according to the references, see:. Lev I.J., Ishikawa K., Bhacca N.S., and Griffin G.W. J. Org. Chem. 41 (1976) 2654-2656
30. Sakai T., Amano E., Kawabata A., and Takeda A. J. Org. Chem. 45 (1980) 43-47
31. 3, 300 MHz) δ 3.97 (s, 3H), 4.08 (dt, J = 6.6 and 1.2 Hz, 2H), 5.30-5.37 (m, 2H)
32. For the similar enaminobutyrolactones, see:. Duron S.G., and Gin D.Y. Org. Lett. 3 (2001) 1551-1554
33. Bower J.F., Szeto P., and Gallagher T. Org. Lett. 9 (2007) 4909-4912