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Halogenoarylation of allyl isothiocyanate: Synthesis of 2,5-disubstituted 2-thiazolines

โœ Scribed by Mykola D. Obushak; Volodymyr V. Karpyak; Mykola I. Ganushchak

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
239 KB
Volume
10
Category
Article
ISSN
1042-7163

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โœฆ Synopsis

A new approach to the synthesis of 2-R-5-benzyl-2-thiazolines with the use of chloro-and bromoarylation products of allyl isothiocyanate with arenediazonium halides was elaborated. The isothiocyanates obtained were reacted with ammonia, aliphatic or aromatic amines, and sodium methoxide. The use of ammonia or weakly basic amines in this reaction allowed. Intermediate thioureas to be isolated. On the basis of 1 H NMR spectra, amino-imino tautomerism of the synthesized 2,5-disubstituted 2thiazolines were analyzed. 2-Arylamino-5-benzyl-2thiazolines exist mainly in the Z-configuration of the imino form.

๐Ÿ“œ SIMILAR VOLUMES

ChemInform Abstract: Preparation of 2,5-
ChemInform Abstract: Preparation of 2,5-Disubstituted 2-Thiazolines.
โœ V. V. KARPYAK; N. D. OBUSHAK; N. I. GANUSHCHAK ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 29 KB ๐Ÿ‘ 1 views

Preparation of 2,5-Disubstituted 2-Thiazolines. -A new synthetic access to the title thiazolines is presented. The isothiocyanates (I) and (VI), prepared by chloroarylation of allylisothiocyanate with aryldiazonium chlorides, undergo cyclization in the presence of bases to afford the target thiazol

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However, many side reactions occur, in contrast to the cyclization of nitrosouracils. When, for instance, a solution of 4-methylamino-5-p-nitrobenzylideneaminouracil(Ia) in nitrobenzene is refluxed for only a short time (2-5 min), fractional crystallization of the product leads to a 40 % yield of 7-