Synthesis of heterocyclics via enamines--IX: reactions of 1-substituted-4,4, 6-trimethyl-1, 4-dihydropyrimidine-2(3h)thione derivatives with dihalocarbenes

Harjit Singh, ; Singh, Paramjit (1981) Synthesis of heterocyclics via enamines--IX: reactions of 1-substituted-4,4, 6-trimethyl-1, 4-dihydropyrimidine-2(3h)thione derivatives with dihalocarbenes Tetrahedron, 37 (6). pp. 1215-1219. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)92053-8

Abstract

Dichloroarbene with 1-substituted 4,4,6 trimethyl- 1,4 dihydropyrimidine 2(3H) thione derivatives (2) formed 7,7-dichloro 3 [(dichloromethyl)thio]-2-substituted-1,5,5-trimethyl-2,4-diazabicyclo[4,1.0] hept-3-ene (3) and 7,7-dichloro-2-substituted-1,5,5-trimethyl-2,4-diazabicyclo [4.1.0] heptane-3 thione (4). On heating as such or under acidic or basic conditions, 3 changed to the corresponding 4 quantitatively. Diiodocarbene with 2 (R=CH3, Ph) formed mainly the corresponding 1-substituted 4,4,6-trimethyl-1,4-dihydropyrimidine-2 one 7 (R=CH3 Ph) 7 (R=CH3).

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