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Synthesis and anti-inflammatory activity of 8H-1-thia-8-aza-dibenzo[e,h]azulenes

✍ Scribed by Ivana Ozimec Landek; Dijana Pešić; Mladen Merćep; Barbara Stanić; Milan Mesić

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
162 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Synthesis of a novel class of fused heterotetracyclic compounds, 8__H__‐1‐thia‐8‐aza‐dibenzo[e,h]azulenes (VII), is described. Starting N‐benzoyl‐protected 5__H__‐dibenzo[b,f]azepine (XI, PG = Bz) was oxidized to 5‐benzoyl‐10,11‐epoxy‐10,11‐dihydro‐5__H__‐dibenzo[b,f]azepine (2), which subsequently rearranged in Lewis acid‐induced epoxide ring opening to give 5‐benzoyl‐5,11‐dihydro‐10__H__‐dibenzo[b,f]azepin‐10‐one (3). Vilsmeier reaction of 3 provided β‐chlorovinyl aldehyde 4 that readily cyclized with ethyl 2‐mercaptoacetate to form dibenzazepino[4,5]‐fused thiophene structure 5. Further transformation of substituent at C‐2 position of 5 and N‐deprotection led to final aminoalkoxy derivatives 9. All compounds with tetracyclic skeleton were tested in vitro for their anti‐inflammatory activity. J. Heterocyclic Chem., (2011).

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