EventsThe 4th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-4-01854
This submission belongs to the session a. General Organic Synthesis of the event The 4th International Electronic Conference on Synthetic Organic Chemistry
Published date
11 Sep, 2000
Citation
Anatoly D. Shutalev, A New Approach to the Synthesis of Hydrogenated Pyrimidine-2-imines, in Proceedings of The 4th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2000, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-4-01854
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A New Approach to the Synthesis of Hydrogenated Pyrimidine-2-imines

Anatoly D. Shutalev 1
1. Department of Organic Chemistry, State Academy of Fine Chemical Technology, Vernadsky Avenue 86, Moscow 117571, Russia
Abstract
A new convenient method for the synthesis of hydrogenated 2-cyaniminopyrimidines has been developed. This method is based on preparation of a-tosyl substituted N-cyanoguanidines 11 followed by reaction with enolates of a-functionally substituted ketones to give 5-functionalized 2-cyanimino-4-hydroxypyrimidines 12, 13, 15, 16. All the obtained hydroxypyrimidines are readily converted into the corresponding 5-functionalized 2-cyanimino-1,2,3,4-tetrahydrohydropyrimidines 17-20 by heating in the presence of acids. Treatment of 5-acetyl-4-hydroxypyrimidines 12 with aq. KOH gives 4-hydroxypyrimidines 21 in result of removing the acetyl group
Keywords
N-cyanoguanidine
N-cyano-N'-(1-tosyl-1-alkyl)guanidines
a-functionally substituted ketones
2-cyanimino-4-hydroxyhexahydropyrimidines
2-cyanimino-1,2,3,4-tetrahydropyrimidines
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