Synthesis of heterocyclic compounds via enamines. Part 8. Acid-catalysed transformations in 4,4,6-trimethyl-1,4-dihydropyrimidine-2(3H)-thione derivatives and related compounds

Harjit Singh, ; Singh, Paramjit (1980) Synthesis of heterocyclic compounds via enamines. Part 8. Acid-catalysed transformations in 4,4,6-trimethyl-1,4-dihydropyrimidine-2(3H)-thione derivatives and related compounds Journal of the Chemical Society, Perkin Transactions 1 . pp. 1013-1018. ISSN 0300-922X

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Official URL: http://www.rsc.org/publishing/journals/P1/article....

Related URL: http://dx.doi.org/10.1039/P19800001013

Abstract

1-Substituted 4,4,6-trimethyl-1,4-dihydropyrimidine-2(3H)-thiones (2) on heating in 11M-HCl at 100-110° are converted into the corresponding 2-substituted-amino-4,6,6-trimethyl-6H-1,3-thiazines (4) and/or thioureas. But at 95-100°, Dimroth rearrangement products, e.g, the corresponding 2-substituted-amino-4,4,6-trimethyl 4H-1,3-thiazines (3) are formed.

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