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Paper | Regular issue | Vol 78, No. 10, 2009, pp. 2489 - 2507
Published online: 15th July, 2009
DOI: 10.3987/COM-09-11755
2,8-Dithia-dibenzo[e,h]azulenes and Their 8-Oxa Analogs. Synthesis and Anti-inflammatory Activity

Ivana Ozimec Landek,* Dijana Pešić, Predrag Novak, Barbara Stanić, Krunoslav Nujić, Mladen Merćep, and Milan Mesić

*IRU Chemistry, GlaxoSmithKline Research Centre Zagreb Limited, Prilaz baruna Filipovića 29, 10000 Zagreb, Croatia

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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