The facile synthesis of 1-benzoazepine derivatives via gold-catalyzed regioselective cycloisomerization reactions of N-(o-alkynylaryl)-N-vinyl sulfonamides

Undeela, Sridhar; Ravikumar, Gurram; Nanubolu, Jagadeesh Babu; Singarapu, Kiran Kumar; Menon, Rajeev S.

The facile synthesis of 1-benzoazepine derivatives via gold-catalyzed regioselective cycloisomerization reactions of N-(o-alkynylaryl)-N-vinyl sulfonamides

2016

Undeela, Sridhar | Ravikumar, Gurram | Nanubolu, Jagadeesh Babu | Singarapu, Kiran Kumar | Menon, Rajeev S.

Gold-catalyzed, regioselective cycloisomerization of N-(o-alkynylaryl)-N-vinyl sulfonamides afforded high yields of 2-sulfonylmethyl-1-benzoazepine derivatives. This 7-endo-dig selective cyclization proceeds via the incorporation of an exocyclic double bond by a labile 1-benzoazepine intermediate. The cyclization substrates were assembled in two steps from readily available materials using Sonogashira coupling and a Cs₂CO₃-mediated formal vinylic substitution.

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