Thieno azepinones

Other examples of mono-alkylation include thieno azepinone 118 (Scheme 23, Section 2.1.3.3 (1999PHA645)), benzodiazepine dione 221 (Scheme 46, Section 3.1.1.2 (1993MI249)) and 7,12-dihydro-6H-[l]benzothiepino[5,4- 7]indole (2006BMCL3233). 

Alkylation of 1 with phenacyl bromide derivatives in the presence of sodium ethoxide gave tricarbonyl 145, which were cyclized to ben-zo[fr]thiophenes 146 upon treatment with La wesson s reagent (99JHC687). Tetrahydrobenzothiophenes 146 with hydroxylamine hydrochloride afforded syn/antioximes 147, which upon treatment with PPA underwent a regiospecific ring expansion to thieno[3,2-c]azepinones 148 (99JHC687). 

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