Synthesis of 4,5-bridged carbazoles

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Abstract
Condensation of 2,2′-bis(bromomethyl)-6-nitrobiphenyl with sodium sulphide gives 5,7-dihydro-1-nitrodibenzo-[c,e]thiepin which, on heating with triphenylphosphine, undergoes reductive cyclisation through a nitrene intermediate to form 8,10-dihydrothiepino[3,4,5,6-def]carbazole. The N-diethylaminoethyl derivative was prepared for pharmacological examination. This route is extended to the synthesis of analogous oxepino-, azepino-, and cyclohepta-carbazoles. 1-Benzamido-5,7-dihydrodibenzo[c,e]thiepin is dehydrated by polyphosphoric acid to form 6,8-dihydro-2-phenylthiepino[3,4,5,6-lmn]phenanthridine but oxepino- and azepino-phenanthridines could not be prepared similarly.

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