Stereodefined ring contraction-rearrangement of thiocoumarins to new fused benzo[b]thiophene derivatives

Tetrahedron

Volumn 67, Issue 3, 2011, Pages 608-611

  Cordaro, Massimiliano ^a   Grassi, Giovanni ^a   Rescifina, Antonio ^b   Chiacchio, Ugo ^b   Risitano, Francesco ^a   Scala, Angela ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

1,3 Cycloaddition; 1,3 Oxazolium 5 oxides; Domino reaction; Stereoselectivity

Indexed keywords

BENZOTHIOPHENE DERIVATIVE; COUMARIN DERIVATIVE; THIOCOUMARIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY;

EID: 78650515652     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.061     Document Type: Article

References (21)

1. R. Huisgen, H. Gotthardt, H.O. Bayer, and F.C. Schaefer Chem. Ber. 45 1970 28 29
2. A. Padwa, R. Lim, J.G. MacDonald, H.L. Gingrich, and S.M. Kellar J. Org. Chem. 50 1985 3816 3823 and references therein
3. T.A. Keating, and R.W. Amstrong J. Am. Chem. Soc. 118 1996 2574 2583
4. N.K. Nayyar, D.R. Hutchinson, and M.J. Martinelli J. Org. Chem. 62 1997 982 991
5. M.T. Bilodeau, and A.M. Cunningham J. Org. Chem. 63 1998 2800 2801
6. G. Grassi, F. Risitano, F. Foti, M. Cordaro, G. Bruno, and F. Nicol Chem. Commun. 2003 1868 1869
7. H.L. Gingrich, and J.S. Baum I.J. Turchi, Oxazoles Vol. 45 1986 Wiley-Interscience New York, NY 731 961
8. K.T. Potts A. Padwa, 1,3-Dipolar Cycloadditions Chemistry Vol. 2 1986 Wiley-Interscience New York, NY 277 406
9. C. Cativiela, and M. Diaz-de-Villegas D.C. Palmer, The Chemistry of Heterocyclic Compounds Oxazoles, Synthesis, Reactions, and Spectroscopy, Part B Vol. 60 2004 John Wiley New York, NY
10. M. Cordaro, G. Grassi, F. Risitano, and A. Scala Tetrahedron 66 2010 2713 2717
11. G. Bruno, F. Nicol, A. Rotondo, M. Cordaro, F. Risitano, and G. Grassi Acta Crystallogr. C61 2005 610 612
12. The configuration of 4 has been assigned by inference.
13. X-ray data to be submitted to Acta Crystallogr.
14. -).
15. H. Hofmann, and G. Salbeck Angew. Chem., Int. Ed. Engl. 8 1969 456
16. D.D. MacNicol, and J.J. McKendrick Tetrahedron Lett. 28 1973 2593 2594
17. S. Peddibhotla, and J.J. Tepe J. Am. Chem. Soc. 126 2004 12776 12777
18. C.A. Maryanoff, and I.J. Turchi Heterocycles 35 1993 649 657
19. O. Meth-Cohn, and B. Tarnowski Synthesis 1978 56 58
20. R. Huisgen, H. Gotthardt, and H.O. Bayer Angew. Chem., Int. Ed. Engl. 3 1964 135 136
21. H.O. Bayer, H. Gotthardt, and R. Huisgen Chem. Ber. 103 1970 2356 2367