Novel isocyanide-based three-component reaction: a facile synthesis of substituted 1H-chromeno[2,3-d]pyrimidine-5-carboxamides

被引:32
作者
Soleimani, Ebrahim [1 ,2 ]
Ghorbani, Somayeh [1 ]
Ghasempour, Hamid Reza [2 ]
机构
[1] Razi Univ, Dept Chem, Kermanshah 6714967346, Iran
[2] Islamic Azad Univ, Sci & Res Branch, Dept Biotechnol & Chem Engn, Kermanshah, Iran
基金
美国国家科学基金会;
关键词
Chromeno[2,3-d]pyrimidine; Multicomponent reactions; Benzopyran; Salicylaldehyde; Barbituric acid; Isocyanide; MULTICOMPONENT REACTIONS SYNTHESIS; ORGANIC-SYNTHESIS; CONDENSATION; STRATEGIES; DISCOVERY; CHEMISTRY;
D O I
10.1016/j.tet.2013.06.080
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and efficient method for the synthesis of 1H-chromeno[2,3-d]pyrimidine-5-carboxamide derivatives via a one-pot, three-component reaction of an isocyanide, barbituric acid, and a salicylaldehyde in the presence of acetic acid in ethanol/water mixture at 75 degrees C is reported. This high atom economy reaction led to the construction of one benzopyran ring, and one amide group in a single synthetic step. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8511 / 8515
页数:5
相关论文
共 43 条
[1]   Diblydropyrido[2,3-d]pyrimidines as a new class of antfleishmanial agents [J].
Agarwal, A ;
Ramesh ;
Ashutosh ;
Goyal, N ;
Chauhan, PMS ;
Gupta, S .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (24) :6678-6684
[2]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[3]   Pd-assisted multicomponent synthesis of heterocycles [J].
Balme, G ;
Bossharth, E ;
Monteiro, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111
[4]  
Banfi L., 2005, Organic Reactions, V65, P1, DOI [10.1002/0471264180.or065.01, DOI 10.1002/0471264180.0R065.01]
[5]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[6]  
2-A
[7]   Synthesis and antigenotoxic activity of some naphtho[2,1-b] pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives [J].
Chabchoub, Fakher ;
Messaad, Mehdi ;
Ben Mansour, Hedi ;
Chekir-Ghedira, Leila ;
Salem, Mansour .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (05) :715-718
[8]   Synthesis, antifungal activity and CoMFA analysis of novel l,2,4-triazolo[1,5-a]pyrimidine derivatives [J].
Chen, Qiong ;
Zhu, Xiao-Lei ;
Jiang, Li-Li ;
Liu, Zu-Ming ;
Yang, Guang-Fu .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (03) :595-603
[9]  
Cheng C. P., 2009, BIOORGAN MED CHEM, V17, P6137
[10]   Synthesis of 2,3,4a,11b-tetramydro-oxazino[2,3-c]benzopyran-9-carbonitriles as ATP-sensitive potassium channel openers [J].
Cheng, CY ;
Chiu, HI ;
Chang, MJ ;
Lin, YC ;
Tsai, MC ;
Yu, HC .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (05) :463-468