Iodine-catalyzed formation of aza-dienes: A novel synthesis of angularly fused hexahydropyrano- and furo[3,2-c]quinoline derivatives

Tetrahedron Letters

Volumn 52, Issue 7, 2011, Pages 761-763

  Reddy, B V Subba ^a   Grewal, Harish ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Angularly fused quinoline derivatives; Imino Diels Alder reaction; Molecular iodine

Indexed keywords

ALKADIENE; ANILINE DERIVATIVE; FURAN DERIVATIVE; IODINE; N METHYL HEXAHYDRO 2H PYRANO[3,2 C]QUINOLINE; N METHYL HEXAHYDROFURO[3,2 C]QUINOLINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST SUPPORT; CYCLOADDITION; SYNTHESIS;

ALNUS;

EID: 78651402694     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.12.003     Document Type: Article

References (40)

1. S.M. Weinreb B.M. Trost, I. Fleming, L.A. Paquette, Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford 401 449
2. D.L. Boger, and S.M. Weinreb Hetero-Diels-Alder Methodology in Organic Synthesis 1987 Academic San Diego Chapters 2 and 9
3. N. Yamada, S. Kadowaki, K. Takahashi, and K. Umezu Biochem. Pharmacol. 44 1992 1211
4. K. Faber, H. Stueckler, and T. Kappe Heterocycl. Chem. 21 1984 1177
5. J.V. Johnson, S. Rauckman, P.D. Baccanari, and B. Roth J. Med. Chem. 32 1989 1942
6. E.A. Mohammed Chem. Pap. 48 1994 261 Chem. Abstr. 1995, 123, 9315x
7. L.S. Povarov Russ. Chem. Rev. 36 1967 656
8. S. Murata, K. Teramoto, M. Miura, and M. Nomura Heterocycles 34 1992 1177
9. A.R. Katritzky, B. Rachwal, and S. Rachwal J. Org. Chem. 60 1995 2588
10. R. Chen, and C. Qian Synth. Commun. 32 2002 2543
11. J. Cabral, and P. Laszlo Tetrahedron Lett. 30 1989 7237
12. B. Crousse, J.P. Begue, and D.B. Delpon Tetrahedron Lett. 39 1998 5765
13. G. Babu, and P.T. Perumal Tetrahedron Lett. 39 1998 3225
14. J.S. Yadav, B.V.S. Reddy, K. Sadasiv, and P.S.R. Reddy Tetrahedron Lett. 43 2002 3853
15. X.-F. Lin, S.-L. Cui, and Y.-G. Wang Tetrahedron Lett. 47 2006 4509
16. D.F. Worth, S.C. Perricone, and E.F. Elsager J. Heterocycl. Chem. 7 1970 1353
17. Y. Ma, C. Qian, M. Xie, and J. Sun J. Org. Chem. 64 1999 6462
18. S. Kobayashi, M. Araki, H. Ishitani, S. Nagayama, and I. Hachiya Synlett 1995 233
19. M. Hadden, and P.J. Stevenson Tetrahedron Lett. 40 1999 1215
20. Y. Makioka, T. Shindo, Y. Taniguchi, K. Takaki, and Y. Fujwara Synthesis 1995 801
21. R.A. Batey, P.D. Simoncic, D. Lin, R.P. Smyj, and A.J. Lough Chem. Commun. 1999 651
22. R.A. Batey, D.A. Powell, A. Acton, and A.J. Lough Tetrahedron Lett. 42 2001 7935
23. H. Togo, and S. Iida Synlett 2006 2159
24. W.-Y. Chen, and J. Lu Synlett 2005 1337
25. L. Royer, S.K. De, and R.A. Gibbs Tetrahedron Lett. 46 2005 4595
26. B.K. Banik, M. Fernandez, and C. Alvarez Tetrahedron Lett. 46 2005 2479
27. S.-Y. Wang Synlett 2004 2642
28. S. Ko, M.N.V. Sastry, C. Lin, and C.-F. Yao Tetrahedron Lett. 46 2005 5771
29. J.S. Yadav, B.V.S. Reddy, and S.R. Hashim J. Chem. Soc., Perkin Trans. 1 2000 3082
30. J.S. Yadav, B.V.S. Reddy, K. Premalatha, and T. Swamy Tetrahedron Lett. 46 2005 2687
31. J.S. Yadav, B.V.S. Reddy, G. Sabitha, and G.S.K.K. Reddy Synthesis 2000 1532
32. J.S. Yadav, B.V.S. Reddy, C.V. Rao, P.K. Chand, and A.R. Prasad Synlett 2001 1638
33. J.S. Yadav, B.V.S. Reddy, M.S. Reddy, and A.R. Prasad Tetrahedron Lett. 43 2002 9703
34. Y. Sato, Y. Ban, T. Aoyama, and H. Shirai J. Org. Chem. 41 1976 1962
35. X.-M. Zhang, and P.S. Mariano J. Org. Chem. 56 1991 1655
36. J.R. Hwu, and K.Y. King Chem. Eur. J. 11 2005 3805
37. 3b,d Spectral data for new products, 3g-l are reported in Supplementary data.
38. B. Karimi, and B. Golshani J. Org. Chem. 65 2000 7228
39. J.S. Yadav, B.V.S. Reddy, A.S. Reddy, S.Ch. Reddy, and S.S. Raju Tetrahedron Lett. 50 2009 6631
40. J.S. Yadav, P.K. Chand, and S. Anjaneyulu Tetrahedron Lett. 43 2002 3783