Copper-catalyzed synthesis of (E)-2,4-diaryl-6-styrylpyrimidines from distyrylketones and benzamidines

被引：2

作者：

Li, Guorui ^{[1
]}

Wang, Yue ^{[1
]}

Li, Zheng ^{[1
]}

机构：

[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2024年 / 1297卷

基金：

中国国家自然科学基金;

关键词：

6-Styrylpyrimidine; Aza-Michael reaction; Distyrylketone; Amidine; Synthesis; PYRIMIDINES; DERIVATIVES;

D O I：

10.1016/j.molstruc.2023.137022

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient method for the synthesis of (E)-2,4-diaryl-6-styrylpyrimidines by copper-catalyzed reactions of distyrylketones with benzamidines through aza-Michael addition/nucleophilic addition/aerobic oxidative dehydrogenation cascade reactions is described. The salient features for this protocol are the use of easy-to-obtain starting materials, inexpensive catalyst, wide range of substrates and functional group tolerance, high atom economy, high yield, and simple operation procedures. The method can also be extended to gram scale.

引用

页数：9

共 34 条

[1] Microwave-assisted simple, one-pot, four-component synthesis of 2,4,6-triarylpyrimidines under solvent-free conditions [J].

Adib, Mehdi ;

Mahmoodi, Niusha ;

Mahdavi, Mohammad ;

Bijanzadeh, Hamid Reza .

TETRAHEDRON LETTERS, 2006, 47 (52) :9365-9368

[2] Antimalarial activity and synthesis of new trisubstituted pyrimidines [J].

Agarwal, A ;

Srivastava, K ;

Puri, SK ;

Chauhan, PMS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (12) :3130-3132

[3] Antimalarial activity of 2,4,6-trisubstituted pyrimidines [J].

Agarwal, A ;

Srivastava, K ;

Puri, SK ;

Chauhan, PMS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) :1881-1883

[4] Regiospecific Photocyclization of Mono- and Bis-Styryl-Substituted N-Heterocycles: A Synthesis of DNA-Binding Benzo[c]quinolizinium Derivatives [J].

Aliyeu, Tseimur M. ;

Berdnikova, Daria V. ;

Fedorova, Olga A. ;

Gulakova, Elena N. ;

Stremmel, Christopher ;

Ihmels, Heiko .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :9075-9085

[5] Anticancer activities of some newly synthesized pyridine, pyrane, and pyrimidine derivatives [J].

Amr, Abdel-Galil E. ;

Mohamed, Ashraf M. ;

Mohamed, Salwa F. ;

Abdel-Hafez, Nagla A. ;

Hammam, Abu El-Fotooh G. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (16) :5481-5488

[6]

Azas Nadine, 2003, Farmaco (Lausanne), V58, P1263, DOI 10.1016/j.farmac.2003.07.009

[7] SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY OF TRISUBSTITUTED PYRIMIDINES AND TRIAZINES [J].

BENNETT, GB ;

MASON, RB ;

ALDEN, LJ ;

ROACH, JB .

JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (07) :623-628

[8] ANTIHYPERTENSIVE ACTIVITY OF 6-ARYLPYRIDO[2,3-D]PYRIMIDIN-7-AMINE DERIVATIVES [J].

BENNETT, LR ;

BLANKLEY, CJ ;

FLEMING, RW ;

SMITH, RD ;

TESSMAN, DK .

JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (04) :382-389

[9] Styryl Group, a Friend or Foe in Medicinal Chemistry [J].

Bhurta, Deendyal ;

Bharate, Sandip B. .

CHEMMEDCHEM, 2022, 17 (07)

[10]

BONDAVALLI F, 1992, FARMACO, V47, P171

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