Issue 0, 1981
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Unexpected substitution of the acyl group in isothiazole-ring formation. Attempted conversion of 1-acyl-2,2-diaminoethylenes into 2-acyl-3,3-diaminoacrylonitriles

Srinivasachari Rajappa,   Mohan D. Nair,   Bhagwan G. Advani  and  Ramaswami Sreenivasan  

Abstract

2-(Acylmethylene) hexahydropyrimidines (7) have been converted into the corresponding benzoyl isothiocyanate adducts (8), treatment of which with sulphuryl chloride gave the 3-chloroisothiazolo[2,3-a]pyrimidine (10) instead of the expected 3-acyl compound (9). Oxidation of the adduct (8c) by bromine gave the isothiazolo[2,3-a]-pyrimidine (9c) in low yield; this failed to undergo base-catalysed fragmentation to the nitrile (13c). Finally, the α-acyl-α-cyanomethylenehexahydropyrimidines (13) were prepared from the phenacyl- and 2-thenoylmethyl-cyanides (11) by condensation with 1-methyl-2-methylthio-1,4,5,6-tetrahydropyrimidine (12).

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/P19810003161
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 3161-3163

Permissions

Request permissions

Unexpected substitution of the acyl group in isothiazole-ring formation. Attempted conversion of 1-acyl-2,2-diaminoethylenes into 2-acyl-3,3-diaminoacrylonitriles

S. Rajappa, M. D. Nair, B. G. Advani and R. Sreenivasan, J. Chem. Soc., Perkin Trans. 1, 1981, 3161 DOI: 10.1039/P19810003161

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements