Novel synthesis of naphtho[2,1-b]pyrano pyrrolizidines and indolizidines through intramolecular 1,3-dipolar cycloaddition reaction

Tetrahedron Letters

Volumn 51, Issue 23, 2010, Pages 3065-3070

  Kathiravan, Subban ^a   Vijayarajan, Devannah ^a   Raghunathan, Raghavachary ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

1,3 Dipolar cycloaddition; Azomethine ylides; Baylis Hillman adduct; Indolizidines; Pyrrolizidines

Indexed keywords

AZOMETHINE YLIDE; INDOLIZIDINE DERIVATIVE; PYRAN DERIVATIVE; PYRROLIZIDINE DERIVATIVE;

1,3 DIPOLAR CYCLOADDITION REACTION; ARTICLE; BAYLIS HILLMAN REACTION; BIOLOGICAL ACTIVITY; CHEMICAL REACTION; CROSS LINKING; CYCLOADDITION; DIPOLE; ONE POT SYNTHESIS; STEREOCHEMISTRY; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

EID: 77953123435     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.017     Document Type: Article

References (32)

1. Decosterd L.A., Parsons I.C., Gustafson K.R., Cardellina II J.H., McMahon J.B., Cragg G.M., Murata Y., Pannell L.K., Steiner J.R., Clardy J., and Boyd M.R. J. Am. Chem. Soc. 115 (1993) 6673-6679
2. Bukuru J.F., Van T.N., Puyvelde L.V., Mathenge S.G., Mudida F.P., and Kimpe N.D. J. Nat. Prod. 65 (2002) 783-785
3. Gemert B.V. Benzo and Naphthopyrans (Chromenes). In: Crano J.C., and Guglielmetti R. (Eds). Organic Photochromic and Thermochromic Compounds Vol. 1 (1999), Plenum Press, New York Chapter 3
4. Michael J.P. Nat. Prod. Rep. 18 (2001) 520-542 and references for previous reviews cited therein
5. For pyrrolizidine alkaloids, see:. Liddell J.R. Nat. Prod. Rep. 18 (2001) 441-447
6. Harborne J.B. Nat. Prod. Rep. 18 (2001) 361-379 and references therein
7. Driver H.D., and Mattocks A.R. Chem. Biol. Interact. 51 (1984) 201-208
8. Pyne S.G., and Tang M. Curr. Org. Chem. 9 (2005) 1393-1418
9. Coldham I., and Hufton R. Chem. Rev. 105 (2005) 2765-2810
10. Pandey G., Banerjee P., and Gadre S.R. Chem. Rev. 106 (2006) 4484-4517
11. Broggini G., and Zecchi G. Synthesis (1999) 905-917
12. Pandey G., Sahoo A.K., and Bagul T.D. Org. Lett. 2 (2000) 2299
13. Vedejs E., Klapers A., Naidu B.N., Piotrowski D.W., and Tucci F.C. J. Am. Chem. Soc. 122 (2000) 5401-5404
14. Li Y., and Marks T.J. J. Am. Chem. Soc. 120 (1998) 1757-1771
15. Back T.G., and Nakajima K. Org. Lett. 1 (1999) 261-264
16. Lesma G., Colombo A., Sacchetti A., and Silvani A. J. Org. Chem. 74 (2009) 590-596
17. Basaviah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811-891
18. Ciganek E. In Organic Reactions Vol. 51 (1997), Wiley, New York pp 201-350
19. Drews S.E., and Emsile N.D. J. Chem. Soc., Perkin Trans. 1 (1982) 2079-2083
20. Roush W.R., and Brown B.B. J. Org. Chem. 58 (1993) 2151-2161
21. Jenn T., and Heissler D. Tetrahedron 54 (1998) 97-106
22. Grassi D., Lippuner V., Aebi M., Brunnerm J., and Vasella A. J. Am. Chem. Soc. 119 (1997) 10992-10999
23. Mateus C.R., Feltrin M.P., Costa A.M., Coelho F., and Almeida W.P. Tetrahedron 57 (2001) 6901-6908
24. Basavaiah D., and Hyma R.S. Tetrahedron 52 (1996) 1253-1258
25. Kathiravan S., and Raghunathan R. Synlett (2009) 1126-1129
26. Purusothaman S., and Raghunathan R. Tetrahedron Lett. 50 (2009) 6848-6851
27. Suresh Babu A.R., Raghunathan R., and Satiskumar B.K. Tetrahedron Lett. 50 (2009) 2818-2821
28. Poornachandran M., and Raghunathan R. Tetrahedron 64 (2008) 6461-6474
29. Poornachandran M., and Raghunathan R. Tetrahedron: Asymmetry 19 (2008) 2177-2183
30. 3Br: C, 71.77; H, 5.55; N, 2.99. Found: C, 71.89; H, 5.49; N, 3.06.
31. Nirmala S., Theboral Sugi Kamala E., Sudha L., Kathiravan S., and Raghunathan R. Acta Crystallogr., Sect. E 65 (2009) o1938
32. Gunasekaran B., Kathiravan S., Raghunathan R., Chakkaravarthi G., and Manivannan V. Acta Crystallogr., Sect. E 65 (2009) o2550