CYCLOADDITION REACTIO.NS WITH CONDENSED THIOPHENS DERIVED FROM ALKYL HETEROAROMATIC CARBONITRILES

Abstract

This work has been carried out to investigate the reaction of 3-amino-Soxa-2- thia-cyclopenta[a]naphthdene-4-one 183 b with dimethyl -acetylenedicarboxylate (DMAD) at room temperature afforded C-1 alkylation product. On the other hand, reaction of 17-amino- l 5-methyl-11-oxa-16-thia-cyclopenta[a]pherianthrene-12-one 314 with DMAD afforded the condensed thienopyridine derivative 316 that cyclized further to J j 7 upon heating in xylene. The reaction of _314 with acrylonitrile and with 4-phenyl-

1,2,4-triazol ine-3,5-dione afforded compounds 3 22 and 330 with loss of

H2S via the expcted [4+2] cycloaddition sequence.