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Communication | Regular issue | Vol 16, No. 1, 1981, pp.49-52
Published online, 1st January, 1970
DOI: 10.3987/R-1981-01-0049
Cyclization of Guanidines with α,β-Unsaturated Ketones: Improved Synthesis of 2-Aminodihydropyrimidine Derivatives Containing Guanidine Moiety

Yong Hae Kim,* Cheol Min Yoon, and Nam Jin Lee

*Department of Chemistry, The Korea Advanced Institute of Science, P. O. Box 150 Chong yang ni, Seoul, Korea


3,4-Dihydro-2-amino pyrimidine derivatives 4a, 4b, 4c, 4d, 4e and 4f containing guanidine moiety were successfully synthesized by cyclizatian of free N-monosubstituted guanidines with α,β-unsaturated ketones in tertiary butanol at 25°C. These products are the first examples to be isolated as pure compounds which are unstable in protic solvents such as water, methanol and ethanol. However they are stable in solid states or in aprotic solvents such as dimethyl sulfoxide, dimethyl formamide, pyridine and chloroform.