2227-79-4Relevant articles and documents
MECHANISM OF THE REACTION OF DIPHENYLPHOSPHINODITHIOIC ACID WITH NITRILES
Benner, Steven A.
, p. 1855 - 1858 (1981)
Kinetic studies of the reaction of diphenylphosphinodithioic acid with nitriles support a two step mechanism, the first step being an "ene" reaction.
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Meinhardt,N.A. et al.
, p. 1991 - 1992 (1960)
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An efficient, one-pot, regioselective synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles under solvent-free conditions
Aggarwal, Ranjana,Claramunt, Rosa M.,Hooda, Mona,Jain, Naman,Rozas, Isabel,Sanz, Dionisia,Twamley, Brendan
, (2021/09/29)
In this article, we present an efficient, one-pot regioselective approach towards the synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles obtained during the reaction of α-bromo-1,3-diketones generated in situ by triturating unsymmetrical 1,3-diketones with N-bromosuccinimide, with various thioamides under solvent-free conditions. This environmentally benign protocol showed large functional group tolerance, resulted in the exclusive formation of a single isomer, out of the two possible regioisomers in admirable yields. The structure of the isomeric thiazole was assigned unambiguously on the basis of multinuclear NMR [(1H-13C) HMBC, (1H-13C) HMQC, (1H-15N) HMBC] and X-ray crystallographic studies. The entire protocol is ecologically desirable as it employs no organic solvent.
Transition-Metal-Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur
Chen, Xinzhi,Ge, Xin,Jin, Hao,Qian, Chao,Zhou, Shaodong
supporting information, p. 3403 - 3406 (2021/06/25)
A general method for one-pot synthesis of thioamides is developed through a three-component reaction involving chlorohydrocarbon, amide and elemental sulfur. Such a strategy does not only avoid residual transition metal in the product but also prevent the generation of C?N coupling by-product. The latter is prone to be generated when alkane halide and amine are present. With the protocol proposed in this work, both alkyl and aryl thioamides can be obtained in moderate to excellent yields with a high tolerance of various functional groups. External oxidants are not required in the reaction. In addition, the reaction mechanisms are addressed using a combination of controlling experiments and quantum chemical calculations.