Rajappa, Srinivasachari ; Nair, Mohan D. ; Advani, Bhagwan G. ; Sreenivasan, Ramaswami (1981) Unexpected substitution of the acyl group in isothiazole-ring formation. Attempted conversion of 1-acyl-2,2-diaminoethylenes into 2-acyl-3,3-diaminoacrylonitriles Journal of the Chemical Society, Perkin Transactions 1 . pp. 3161-3163. ISSN 0300-922X
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Official URL: http://pubs.rsc.org/en/content/articlelanding/1981...
Related URL: http://dx.doi.org/10.1039/P19810003161
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).
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 50320 |
| Deposited On: | 23 Jul 2011 07:17 |
| Last Modified: | 23 Jul 2011 07:17 |
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