Abstract
A series of new push-pull compounds were synthesised by reaction of 5-aryl- furan-2-carboxaldehydes and furo[b]pyrrole type aldehydes with benzothiazolium salts. These new condensation products represent highly conjugated systems that have potential biological activity. The reaction of furo[b]pyrrole type aldehydes with benzothiazolium salts give potential precursors of cyanine dyes.
Highlights
Many compounds containing the benzothiazole moiety are reported to be biologically active and good structure-activity relations have been found using QSAR studies [1,2]
In the past we have been interested in the synthesis and reactions of 5-arylfuran-2-carboxaldehydes 1 [5]
We have recently published in this journal the results of the study of the reactions of substituted furan-2-carboxaldehydes and furo[b]pyrrole type aldehydes with hippuric acid [14]
Summary
Many compounds containing the benzothiazole moiety are reported to be biologically active and good structure-activity relations have been found using QSAR studies [1,2]. Many of the published condensation products of 5-arylfuran-2-carboxaldehydes are reported to be biologically active compounds [6,7] or can be used as intermediates in organic synthesis [8,9]. Furo[b]pyrrole type aldehydes 2 and 3 are heteroanalogues of the pentalene dianion [10]. Their full synthesis and properties were described recently [11]. A few condensation products of furo[b]pyrrole type aldehydes have been described [12, 13]. We have recently published in this journal the results of the study of the reactions of substituted furan-2-carboxaldehydes and furo[b]pyrrole type aldehydes with hippuric acid [14]
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