THE CONJUGATE ADDITION OF BENZOYL(THIOACETANILIDES) TO NITROALKENES -SYNTHESIS OF FUNCTIONALIZED THIOPHENES AND PYRROLES

Authors
BOGDANOWICZSZWED K GROCHOWSKI J PALASZ A RYS B SERDA P SOJA D
Citation
K. Bogdanowiczszwed et al., THE CONJUGATE ADDITION OF BENZOYL(THIOACETANILIDES) TO NITROALKENES -SYNTHESIS OF FUNCTIONALIZED THIOPHENES AND PYRROLES, Liebigs Annalen, (9), 1996, pp. 1457-1462
Citations number
19
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
9
Year of publication
1996
Pages
1457 - 1462
Database
ISI
SICI code
0947-3440(1996):9<1457:TCAOBT>2.0.ZU;2-3
Abstract
Reaction of benzoyl(thioacetanilides) 1 with (E)-beta-nitrostyrenes 2 yields enzoyl-5-hydroxyimino-2,3,4,5-tetrahydrothiophenes 7. In PPA me dium the oxime function of 7 undergoes dehydration and hydrolysis lead ing to -2-arylimino-3-benzoyl-2,5-dihydro-5-oxothiophenes 9. Reaction of 7 with hydrochloric acid involves dehydration, hydrolysis and ring transformation to iaryl-3-benzoyl-2,5-dihydro-5-oxo-2-thioxopyrroles 1 0. Acetic anhydride reacts with 7 to yield 4-aryl-2-arylimino-3-benzoy l-2,5-dihydrothiophenes 11.