Construction of dihydropyrimidine skeleton using 1,2,4-trisubstituted-1,3-diaza-1,3-butadienes
Construction of dihydropyrimidine skeleton using 1,2,4-trisubstituted-1,3-diaza-1,3-butadienes
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DOI：
10.1016/j.tetlet.2011.12.111
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发表时间：
2012-02-29
影响因子：
1.8
通讯作者：
Yamaguchi, Masahiko
中科院分区：
文献类型：
--
作者：
Cho, Hidetsura;Nishimura, Yoshio;Yamaguchi, Masahiko
二氢嘧啶环的构建涉及具有 N-保护基团（N-Cbz、N-Boc、N-烷基或 N-苄基）的 1,3-二氮杂-1,3-丁二烯与 α,β-不饱和羰基化合物（例如丙烯酸乙酯和对氯苯基乙烯基酮）的环化。因此，以良好的收率合成了4-二甲基氨基-2苯基-1,4,5,6-四氢嘧啶。随后，用MeI或SiO2进行二甲基氨基的β-消除，以良好的收率得到各种N-保护的2,5-二取代-1,6-二氢嘧啶。值得注意的是，使用4-氯苯基乙烯基酮以优异的产率直接提供二氢嘧啶，而无需四氢嘧啶中间体。 (C) 2011 Elsevier Ltd. 保留所有权利。
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 alpha,beta-unsaturated carbonyl compounds such as ethyl acrylate and p-chlorophenyl vinyl ketone. Consequently, 4-dimethylamino-2phenyl-1,4,5,6-tetrahydropyrimidines were synthesized in good yields. Subsequently, the beta-elimination of the dimethylamino group was carried out with MeI or SiO2 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. (C) 2011 Elsevier Ltd. All rights reserved.