An Unprecedented Approach to 4,5-Disubstituted Pyrimidine Derivatives by a ZnCl2-Catalyzed Three-Component Coupling Reaction

被引：113

作者：

Sasada, Toshiaki ^{[1
]}

Kobayashi, Fuminori ^{[1
]}

Sakai, Norio ^{[1
]}

Konakahara, Takeo ^{[1
]}

机构：

[1] Tokyo Univ Sci, RIKADAI, Dept Pure & Appl Chem, Fac Sci & Technol, Chiba 2788510, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 10期

关键词：

ONE-POT SYNTHESIS; N-HETERO COMPOUNDS; SUBSTITUTED PYRIMIDINES; RING TRANSFORMATION; EFFICIENT SYNTHESIS; AROMATIC NITRILES; STEP SYNTHESIS; CYCLIZATION; GENERATION; PALLADIUM;

D O I：

10.1021/ol900382j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a ZnCl2-catatyzed three-component coupling reaction involving a variety of functionalized enamines, triethyl orthoformate, and ammonium acetate, which leads to the production of 4,5-disubstituted pyrimidine derivatives in a single step. The procedure can be successfully applied to the efficient synthesis of mono- and disubstituted pydmidine derivatives, using methyl ketone derivatives instead of enamines.

引用

页码：2161 / 2164

页数：4

共 50 条

[41] CuBr2-Catalyzed Three-Component Coupling for Synthesis of Quinoline-2,4-dicarboxyl Derivatives
Wang, Kou
Yu, Haofei
Ding, Linfen
Hu, Jianlin
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (07) : 1437 - 1441
[42] Ni-CATALYZED THREE-COMPONENT COUPLING OF 4-METHYLENE-2-OXAZOLIDINONES, ALKYNES, AND TRIMETHYLALUMINUM
Yamahira, Tatsuya
Ninokata, Ryo
Onodera, Gen
Kimura, Masanari
HETEROCYCLES, 2017, 95 (02) : 722 - 729
[43] Room temperature copper-catalyzed 2-functionalization of pyrrole rings by a three-component coupling reaction
Cho, Seung Hwan
Chang, Sukbok
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) : 2836 - 2839
[44] Diversification of 4,5-disubstituted Pyrrolo[3,2-d]-pyrimidines by Microwave Assisted Metal Catalyzed Reaction
Byeon, Jeong Seob
Yum, Eul Kgun
Kim, Yeong-Joon
Journal of the Korean Chemical Society, 2022, 66 (06): : 442 - 450
[45] Regioselective synthesis and antibacterial evaluation of novel bis-pyrimidine derivatives via a three-component reaction
Nosrat O. Mahmoodi
Sajede Shoja
Bahman Sharifzadeh
Mehdi Rassa
Medicinal Chemistry Research, 2014, 23 : 1207 - 1213
[46] Regioselective Three-Component Coupling by the Palladium-Catalyzed Reaction of 2-Fluoroallylic Acetates with Phenols and Imides
Kogawa, Masaki
Watanabe, Hirotaka
Yamamoto, Mitsuaki
Tsuchi, Yukiko
Zhou, Biao
Kawatsura, Motoi
SYNLETT, 2017, 28 (09) : 1071 - 1074
[47] Diversification of 4,5-disubstituted Pyrrolo[3,2-d]-pyrimidines by Microwave Assisted Metal Catalyzed Reaction
Byeon, Jeong Seob
Yum, Eul Kgun
Kim, Yeong-Joon
JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2022, 66 (06): : 442 - 450
[48] Regioselective synthesis and antibacterial evaluation of novel bis-pyrimidine derivatives via a three-component reaction
Mahmoodi, Nosrat O.
Shoja, Sajede
Sharifzadeh, Bahman
Rassa, Mehdi
MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (03) : 1207 - 1213
[49] Synthesis and crystal structures of some new 2-(diphenylamino)-4,5-disubstituted thiazole derivatives
Heydari, Reza
Shahrekipour, Fahimeh
Graiff, Claudia
Tahamipour, Batool
JOURNAL OF CHEMICAL RESEARCH, 2016, (06) : 326 - 330
[50] A novel three-component reaction for the synthesis of new 4-azafluorenone derivatives
Tu, Shujiang
Jiang, Bo
Jiang, Hong
Zhang, Yan
Jia, Runhong
Zhang, Junyong
Shao, Qingqing
Li, Chunmei
Zhou, Dianxiang
Cao, Longji
TETRAHEDRON, 2007, 63 (25) : 5406 - 5414

← 1 2 3 4 5 →