One-Pot Synthesis of Benzoxazole/Benzothiazole-Substituted Esters by Michael Addition: A Selective Construction of C-N/C-S Bonds

Abstract

An efficient and convenient synthesis of benzoxazole/benzothiazole-substituted esters in a one-pot strategy is reported. In this investigation, a selective construction of C-N and C-S bonds via simple addition is performed. Thus, using substituted 2-aminophenols/2-aminobenzenethiols, TMTD (tetramethylthiuram disulfide) and α,β-unsaturated esters as starting substrates, C-N and C-S bonds can be selectively constructed by means of the Michael addition reaction. This protocol features high selectivity, high atomic economy, mild conditions, good functional tolerance and good to excellent yields, showing the potential value for the preparation of some biologically and pharmaceutically active compounds.