TY - JOUR
T1 - Construction of dihydropyrimidine skeleton using 1,2,4-trisubstituted-1,3- diaza-1,3-butadienes
AU - Cho, Hidetsura
AU - Nishimura, Yoshio
AU - Yasui, Yoshizumi
AU - Yamaguchi, Masahiko
N1 - Funding Information:
We appreciate the financial support of the Tohoku University G-COE program ‘IREMC’. This work was also carried out with the financial support of Japan Tobacco Inc. to H.C. We thank Mr. Satoshi Kobayashi for technical support.
Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.
PY - 2012/2/29
Y1 - 2012/2/29
N2 - Construction of a dihydropyrimidine ring was developed that involved the cyclization of 1,3-diaza-1,3-butadienes having an N-protecting group (N-Cbz, N-Boc, N-alkyl, or N-benzyl) with α,β-unsaturated carbonyl compounds such as ethyl acrylate and p-chlorophenyl vinyl ketone. Consequently, 4-dimethylamino-2-phenyl-1,4,5,6-tetrahydropyrimidines were synthesized in good yields. Subsequently, the β-elimination of the dimethylamino group was carried out with MeI or SiO 2 to afford various N-protecting-2,5- disubstituted-1,6-dihydropyrimidines in good yields. Remarkably, the use of 4-chlorophenyl vinyl ketone directly provided the dihydropyrimidine without the tetrahydropyrimidine intermediate in excellent yield.
AB - Construction of a dihydropyrimidine ring was developed that involved the cyclization of 1,3-diaza-1,3-butadienes having an N-protecting group (N-Cbz, N-Boc, N-alkyl, or N-benzyl) with α,β-unsaturated carbonyl compounds such as ethyl acrylate and p-chlorophenyl vinyl ketone. Consequently, 4-dimethylamino-2-phenyl-1,4,5,6-tetrahydropyrimidines were synthesized in good yields. Subsequently, the β-elimination of the dimethylamino group was carried out with MeI or SiO 2 to afford various N-protecting-2,5- disubstituted-1,6-dihydropyrimidines in good yields. Remarkably, the use of 4-chlorophenyl vinyl ketone directly provided the dihydropyrimidine without the tetrahydropyrimidine intermediate in excellent yield.
KW - Cyclization
KW - Cycloaddition
KW - Dienes
KW - Dihydropyrimidine
KW - Heterocycles
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U2 - 10.1016/j.tetlet.2011.12.111
DO - 10.1016/j.tetlet.2011.12.111
M3 - Article
AN - SCOPUS:84856211454
VL - 53
SP - 1177
EP - 1179
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 9
ER -