Abstract
Methods for the synthesis of keto derivatives of the little studied naphtho[1,8-bc]thiophene system have been developed. Using the readily available benzothiophene derivative 6,7-dihydrobenzo[b]thiophen-4(5H)-one 4, a 3-keto-naphtho[1,8-bc]thiophene 14 was synthesized by a tin(IV) chloride catalyzed cyclization of the acid chloride derivative of the saturated acid 13b. The bicyclic ketone 4 was also used to prepare the keto-sulfoxide 7, which was cyclized to the 4-keto-naphtho[1,8-bc]thiophene system 9 in a Pummerer-type rearrangement. Key words: synthesis, organosulfur, naphtho[1,8-bc]thiophenones.
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