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Synthesis and Reactions of 3‐Oxobutyl Isothiocyanate (OB ITC)
Author(s) -
Verma Rajeshwar P.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390073
Subject(s) - chemistry , thiourea , isothiocyanate , amino acid , phenyl isothiocyanate , amine gas treating , bicyclic molecule , organic chemistry , medicinal chemistry , biochemistry
In 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 (NH 2 , 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)