Synthesis and characterization of 2-aminodihydropyrimidines : cyclization of guanidine derivatives with α,β-unsaturated carbonyl compounds2-아미노디히드로피리미딘들의 합성과 분석 : 구아니딘 유도체들과 α,β-불포화된 카아보닐 화합물과의 고리화 반응

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Guanidine ring compounds of 2-aminodihydropyrimidine derivatives were effectively synthesized by the cyclocondensation of free guanidine derivatives with $\alpha,\beta$ unsaturated carbonyl compounds such as benzalacetophenone, methylacrylate, and methylmethacrylate in good yields under mild conditions. The dihydropyrimidine was so unstable at high temperature and in protic solvents even at low temperature that its yield might be seriously effected by solvent and the reaction temperature. The new derivatives of 2-aminodihydropyrimidine were successfully synthesized in good yields under mild conditions and the structure was determined by spectroscopic methods. The steric effect for the cyclocondensation reaction was observed by the alkyl substituents not only in the guanidine derivatives but also in the $\alpha,\beta$-unsaturated carbonyl compounds. Pure 2-amino-3,4-dihydropyrimidine derivatives were isolated and they were found to be unstable in protic solvents such as water, methanol, and ethanol. Their unstability in protic solvents was monitored by $^1H$ nmr and UV spectra. The preferable condition for the synthesis of 2-aminodihydropyrimidine was to keep the reaction temperature low and to use sterically hindered alcohols such as i-propanol and t-butanol.
Advisors
Kim, Yong-Hae김용해
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1982
Identifier
63276/325007 / 000801187
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1982.2, [ iv, 67 p. ]

URI
http://hdl.handle.net/10203/32326
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=63276&flag=dissertation
Appears in Collection
CH-Theses_Master(석사논문)
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