Synthesis and reactivities of 10‐S‐3 trithiadiazapentalene derivatives

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Abstract
1,3‐Bis(p‐substituted‐phenylthiocarbamoyl)‐2‐imidazolidinethiones 3a‐f reacted with bromine to give trithiadiazapentalene derivatives 5a‐f, bearing the exocyclic C‐N double bonds, in moderate yields. The molecular structure of 5b was elucidated by the X‐ray crystallographic analysis. The treatment of 5b‐f with hydrochloric acid gave the ring‐opening products, 1,3‐bis(p‐substituted‐phenylthiocarbamoyl)‐2‐imidazo‐lidinones 9b‐f, accompanied by the production of elemental sulfur. Reduction of 5b, 5d, and 5e with sodium borohydride gave the ring‐opening compounds, 1,3‐bis(p‐substituted‐phenylthiocarbamoyl)‐2‐imidazolidines 13b, 13d, and 13e respectively.