Synthesis and Reactions of 3‐Oxobutyl Isothiocyanate (OB ITC)

Abstract

AbstractIn this review an attempt has been made to compile all the existing comprehensive literature for the synthesis of 3‐oxobutyl isothiocyanate (OB ITC), also known as 4‐isothiocyanato‐2‐butanone, and its reactions with compounds possessing different functional groups, such as amines, diamines, amino alcohols, amino thiols, amino phenols, amino thiophenols, and amino acids. The peculiar behavior of OB ITC is due to its sensitivity towards acids, different products being obtained when the reaction is performed in the absence and in the presence of an acid. The pH of the reaction conditions also plays an important role. Normally, OB ITC gives thiourea derivatives when treated with amines, but reactions become interesting with compounds possessing an amino group together with another functional group (NH2, OH, SH, COOH) in the ortho position, providing condensed bicyclic or tricyclic heterocycles of biological importance, with ring nitrogen and/or sulfur. (© Wiley‐VCH Verlag GmbH & Co KGaA, 69451 Weinheim, Germany, 2003)