Synthesis of benzopyranopyrrolidines via 1,3-dipolar cycloaddition of nonstabilized azomethine ylides with 3-substituted coumarins

Tetrahedron

Volumn 69, Issue 29, 2013, Pages 5884-5892

  Moshkin, Vladimir S ^a   Sosnovskikh, Vyacheslav Ya ^a   Röschenthaler, Gerd Volker ^b  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

^b JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

3 Substituted coumarins; Nonstabilized azomethine ylide 3+2 cycloaddition 1 Benzopyrano 3,4 c pyrrolidines; Regioselectivity; Stereoselectivity

Indexed keywords

AZOMETHINE YLIDE; COUMARIN DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CYCLOADDITION; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 84878833629     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.05.018     Document Type: Article

References (25)

1. O. Tsuge, and S. Kanemasa Adv. Heterocycl. Chem. 45 1989 231 344
2. G. Pandey, P. Banerjee, and S.R. Gadre Chem. Rev. 106 2006 4484 4517
3. C. Nájera, and J.M. Sansano Curr. Org. Chem. 7 2003 1105 1150
4. I. Coldham, and R. Hufton Chem. Rev. 105 2005 2765 2809
5. A. Padwa, and W.H. Pearson Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products Vol. 59 2002 Wiley New York, NY 169 252
6. G.P. Rizzi J. Org. Chem. 35 1970 2069 2072
7. R. Grigg, and S. Thianpatanagul J. Chem. Soc., Chem. Commun. 1984 180 181
8. R. Grigg, M.F. Aly, V. Sridharan, and S. Thianpatanagul J. Chem. Soc., Chem. Commun. 1984 182 183
9. R. Grigg, J. Idle, P. McMeekin, and D. Vipond J. Chem. Soc., Chem. Commun. 1987 49 51
10. R. Grigg, J. Idle, P. McMeekin, S. Surendrakumar, and D. Vipond J. Chem. Soc., Perkin Trans. 1 1988 2703 2713
11. R. Grigg, and D. Vipond Tetrahedron 45 1989 7587 7592
12. O. Tsuge, S. Kanemasa, M. Ohe, and S. Takenaka Bull. Chem. Soc. Jpn. 60 1987 4079 4089
13. T. Dubuffet, O. Muller, S.S. Simonet, J.-J. Descombes, M. Laubie, T.J. Verbeuren, and G. Lavielle Bioorg. Med. Chem. Lett. 6 1996 349 352
14. T. Dubuffet, A. Newman-Tancredi, D. Cussac, V. Audinot, A. Loutz, M.J. Millan, and G. Lavielle Bioorg. Med. Chem. Lett. 9 1999 2059 2064
15. US Patent 5,663,191, 1997
16. US Patent 6,046,207, 2000
17. H.G. Pars, F.E. Granchelli, R.K. Razdan, J.K. Keller, D.G. Teiger, F.J. Rosenberg, and L.S. Harris J. Med. Chem. 19 1976 445 454
18. A.R. Haight, A.E. Bailey, W.S. Baker, M.H. Cain, R.R. Copp, J.A. DeMattei, K.L. Ford, R.F. Henry, M.C. Hsu, R.F. Keyes, S.A. King, M.A. McLaughlin, L.M. Melcher, W.R. Nadler, P.A. Oliver, S.I. Parekh, H.H. Patel, L.S. Seif, M.A. Staeger, G.S. Wayne, S.J. Wittenberger, and W. Zhang Org. Process Res. Dev. 8 2004 897 902
19. T. Kiyoi, M. Reid, S. Francis, K. Davies, S. Laats, D. McArthur, A.-M. Easson, Y. Kiyoi, G. Tarver, W. Caulfield, K. Gibson, G. Wishart, A.J. Morrison, J.M. Adam, and P. Ray Tetrahedron Lett. 52 2011 3413 3416
20. V.S. Moshkin, V.Y. Sosnovskikh, P.A. Slepukhin, and G.-V. Röschenthaler Mendeleev Commun. 22 2012 29 31
21. V.S. Moshkin, V.Y. Sosnovskikh, and G.-V. Röschenthaler Tetrahedron Lett. 53 2012 3568 3572
22. V.S. Moshkin, and V.Y. Sosnovskikh Tetrahedron Lett. 54 2013 2455 2457
23. V.S. Moshkin, and V.Y. Sosnovskikh Tetrahedron Lett. 54 2013 2699 2702
24. F. Orsini, F. Pelizzoni, M. Forte, M. Sisti, F. Merati, and P. Gariboldi J. Heterocycl. Chem. 25 1988 1665 1673
25. S. Mataka, H. Kitagawa, T. Tsukinoki, M. Tashiro, K. Takahashi, and K. Kamata Bull. Chem. Soc. Jpn. 68 1995 1969 1979