Protecting Group Free Synthesis of Carboxyl-substituted Dihydropyrimidines Through Biginelli Reaction

被引：8
|
作者：
Ostapchuk, Eugeniy N. [1 ,2 ]
Plaskon, Andrey S. [1 ,2 ]
Grygorenko, Oleksandr O. [1 ,2 ]
Tolmachev, Andrey A. [1 ,2 ]
Ryabukhin, Sergey V. [1 ,3 ]
机构：
[1] Enamine Ltd, UA-01103 Kiev, Ukraine
[2] Kyiv Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine
[3] Kyiv Natl Taras Shevchenko Univ, Inst High Technol, UA-03187 Kiev, Ukraine
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2013年 / 50卷 / 06期
关键词：
Biginelli reaction; multicomponent reaction; dihydropyrimidines; ureas; chlorotrimethylsilane; ONE-POT SYNTHESIS; COMBINATORIAL CHEMISTRY; MULTICOMPONENT REACTIONS; LIBRARY SYNTHESIS; DOMINO REACTIONS; CHLOROTRIMETHYLSILANE; CONDENSATION; ALDEHYDES; MOLECULES; THIOUREA;
D O I：
10.1002/jhet.1568
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chlorotrimethylsilane-promoted Biginelli-type reaction of benzaldehyde, acetoacetic acid derivatives, and various carboxyl-containing ureas was explored. It was found that the steric load of the urea substituents influenced strongly the reaction outcome; in particular, the method was efficient only in the case of unbranched mono-substituted ureas bearing either aliphatic or aromatic groups. The method allows performing a one-pot, protecting group free synthesis of dihydropyrimidines possessing carboxylic functionality.
引用
收藏
页码：1299 / 1303
页数：5
相关论文
共 50 条
  • [31] An efficient synthesis of β-ketoesters via transesterification and its application in Biginelli reaction under solvent-free, catalyst-free conditions
    Rao, G. B. Dharma
    Acharya, B. N.
    Kaushik, M. P.
    TETRAHEDRON LETTERS, 2013, 54 (48) : 6644 - 6647
  • [32] Strategies toward protecting group-free glycosylation through selective activation of the anomeric center
    Downey, A. Michael
    Hocek, Michal
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 1239 - 1279
  • [33] Ammonium tetrafluoroborate: Novel Unprecedented Catalyst for the Synthesis of 3,4-dihydropyrimidin-2(1H)-ones through Biginelli Reaction
    Verma, Aman
    Chaudhary, Gyanendra
    Verma, Deepti
    Prabhakar, Amit
    Behera, Kamalakanta
    CHEMISTRYSELECT, 2024, 9 (08):
  • [34] Protecting-Group-Free Synthesis of Glycopolymers Bearing Thioglycosides Via One-Pot Monomer Synthesis from Free Saccharides
    Tanaka, Tomonari
    Inoue, Genri
    Shoda, Shin-Ichiro
    Kimura, Yoshiharu
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2014, 52 (24) : 3513 - 3520
  • [35] MICROWAVE-ASSISTED AND IODINE-CATALYZED SYNTHESIS OF DIHYDROPYRIMIDIN-2-THIONES VIA BIGINELLI REACTION UNDER SOLVENT-FREE CONDITIONS
    Liu, Qingjian
    Pan, Ning
    Xu, Jiehua
    Zhang, Wenwen
    Kong, Fanpeng
    SYNTHETIC COMMUNICATIONS, 2013, 43 (01) : 139 - 146
  • [36] Revisit to the Biginelli reaction: a novel and recyclable bioglycerol-based sulfonic acid functionalized carbon catalyst for one-pot synthesis of substituted 3,4-dihydropyrimidin-2-(1H)-ones
    Konkala, Karnakar
    Sabbavarapu, Narayana Murthy
    Katla, Ramesh
    Durga, Nageswar Yadavalli Venkata
    Reddy, Vijai Kumar T.
    Devi, Bethala L. A. Prabhavathi
    Prasad, Rachapudi B. N.
    TETRAHEDRON LETTERS, 2012, 53 (15) : 1968 - 1973
  • [37] Protecting-Group-Free Synthesis of Meridianin A-G and Derivatives and Its Antibiofilm Evaluation
    Geng, Huidan
    Chen, Fei
    Zhao, Yonglong
    Guo, Bing
    Tang, Lei
    Yang, Yuan -Yong
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06) : 3927 - 3934
  • [38] Efficient synthesis of 3-substituted indoles via a base-free copper-catalysed three-component reaction in water
    Jiang, Haojie
    Wang, Leilei
    Xie, Jianwei
    JOURNAL OF CHEMICAL RESEARCH, 2016, (06) : 338 - 340
  • [39] One pot protecting group free synthesis of multifunctional biphenyl methyl-C-β-D-glycosides in aqueous medium
    Misra, Mridul
    Sharma, Rahul
    Kant, Ruchir
    Maulik, P. R.
    Tripathi, R. P.
    TETRAHEDRON, 2011, 67 (04) : 740 - 748
  • [40] BASE-MEDIATED BIGINELLI-LIKE REACTION IGNITED BY AROMATIC ISOCYANATE: A FACILE ONE-POT SYNTHESIS OF N4-ARYL-5-CARBOXYL-6-METHYL CYTIMIDINE DERIVATIVES
    Liang, Chengyuan
    Song, Huihui
    Jiang, Hailong
    Yao, Qizheng
    SYNTHETIC COMMUNICATIONS, 2014, 44 (20) : 2930 - 2935
12345