A Versatile, Unexpected, One-Pot Regioselective Synthesis of a New Class of 1,3-Diazepinoindolones by Reaction of Pyranoindolones with Monosubstituted Ureas

Abstract

The regioselective one-pot synthesis of a new class of 4,6-dihydro[1,3]diazepino[5,6-b]indol-3(2H)-ones, in very good yields, via reaction of pyranoindolones with monosubstituted ureas is described. Reaction of N,N¢-disubstituted ureas with pyranoindolones, under similar conditions, gave the corresponding b-carbolinones. The reaction mechanisms leading to both types of product are discussed and the structures are confirmed by spectroscopic techniques.