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Paper | Regular issue | Vol 81, No. 10, 2010, pp. 2269 - 2290
Published online: 26th August, 2010
DOI: 10.3987/COM-10-12014
Synthesis of Naphtho[2,3-b]- and Naphtho[1,2-b]-fused Thieno[2,3-d][1]benzoxepins and Thieno[2,3-d][1]benzothiepins

Ivana Ozimec Landek,* Dijana Pešić, Rudolf Trojko, Maja Devčić Bogdanović, Mladen Merćep, and Milan Mesić

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

Abstract

Synthesis of four novel classes of structurally related fused hetero-pentacyclic compounds, naphtho[2,3-b]thieno[2,3-d][1]benzothiepins (Ia), naphtho[1,2-b]thieno[2,3-d][1]benzothiepins (IIa), naphtho[2,3-b]thieno[2,3-d][1]benzoxepins (Ib,c) and naphtho[1,2-b]thieno[2,3-d][1]benzoxepins (IIb,c), is described. The key intermediates were the tetracyclic ketones, benzo[b]-naphtho[f]-fused thiepinones 1a,b and oxepinones 1c-f, formed by intramolecular cyclization of the corresponding 2-naphthalenylthio- (2a,b) and 2-naphthalenyloxy-substituted (2c-f) phenylacetic acid derivatives. Reaction of ketones 1a-f with Vilsmeier reagent provided β-chlorovinyl aldehydes 10a-f that readily cyclized with ethyl 2-mercaptoacetate to form thieno[2,3-d]-fused derivatives of benzo-naphtho-thiepins 11a,b and benzo-naphtho-oxepins 11c-f. Reduction of ester group of 11a-f afforded final hydroxymethyl derivatives 12a-f.

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