Abstract
Synthesis of 2, 8-dithia-dibenzo[e, h]azulenes (III, X = S) and their 8-oxa analogs (III, X = O), 1 two novel classes of fused heterocyclic compounds, is described. Starting 11H-dibenzo[b, f]thiepin-10-one, 11H-dibenzo[b, f]oxepin- 10-one and its 2-chloro derivative (1a-c) were oxidized to 1, 2-diketones (2a-c) which subsequently reacted with 2, 2’ -dimethyl thiodiglycolate to form fused thiophene ring by Hinsberg cyclization reaction. Substituents at positions C(1) and C(3) were then further transformed in order to obtain aminoalkoxy derivatives 8-11. Structures of regioisomers 6c and 6d were elucidated using two-dimensional NMR techniques. All compounds with tetracyclic skeleton were tested in vitro for their anti-inflammatory activity.
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