Iodine-catalyzed three-component one-pot synthesis of naphthopyranopyrimidines under solvent-free conditions

被引:45
作者
Kumar, K. Praveen [1 ]
Satyanarayana, S. [1 ]
Reddy, P. Lakshmi [1 ]
Narasimhulu, G. [1 ]
Ravirala, Narender [1 ]
Reddy, B. V. Subba [1 ]
机构
[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India
关键词
3CC Reaction; Molecular iodine; Naphthopyranopyrimidine; NPSR antagonists; MOLECULAR-IODINE; EFFICIENT SYNTHESIS; 4-COMPONENT REACTION; FACILE SYNTHESIS; DERIVATIVES; CONDENSATION; REAGENT; AMINES;
D O I
10.1016/j.tetlet.2012.01.096
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iodine is found to be a highly efficient catalyst for the three-component coupling (3CC) of aldehydes, beta-naphthol, and 1,3-dimethylbarbituric acid under solvent-free conditions to afford the corresponding 8,10-dimethyl-12-aryl-12H-naphtho[1',2'5,6]pyrano[2,3-d]pyrimidine-9,11-diones in good yields with high selectivity. The use of readily available iodine makes this method very simple, convenient, and cost-effective. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1738 / 1741
页数:4
相关论文
共 48 条
[1]   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
[2]   Iodine-catalyzed highly efficient Michael reaction of indoles under solvent-free condition [J].
Banik, BK ;
Fernandez, M ;
Alvarez, C .
TETRAHEDRON LETTERS, 2005, 46 (14) :2479-2482
[3]   Synthesis and antimicrobial activities of novel naphtho[2,1-b]pyran, pyrano[2,3-d]pyrimidine and pyrano[3,2-e][1,2,4]triazolo[2,3-c]-pyrimidine derivatives [J].
Bedair, AH ;
Emam, HA ;
El-Hady, NA ;
Ahmed, KAR ;
El-Agrody, AM .
FARMACO, 2001, 56 (12) :965-973
[4]   4-hydroxycoumarin in heterocyclic synthesis -: Part III.: Synthesis of some new pyrano[2,3-d]pyrimidine, 2-substituted[1,2,4]triazolo[1,5-c]pyrimidine and pyrimido[1,6-b][1,2,4]triazine derivatives [J].
Bedair, AH ;
El-Hady, NA ;
Abd El-Latif, MS ;
Fakery, AH ;
El-Agrody, AM .
FARMACO, 2000, 55 (11-12) :708-714
[5]   Molecular-iodine-catalyzed one-pot synthesis of 1,5-benzodiazepine derivatives under solvent-free conditions [J].
Chen, WY ;
Lu, J .
SYNLETT, 2005, (08) :1337-1339
[6]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[7]  
2-U
[8]   A Simple and Green Approach for the Synthesis of Tetrahydrobenzo[a]xanthen-11-one Derivatives Using Tetrabutyl Ammonium Fluoride in Water [J].
Gao, Shijay ;
Tsai, Chen Hsuan ;
Yao, Ching-Fa .
SYNLETT, 2009, (06) :949-954
[9]   A novel three-component one-pot reaction involving alkynes, urea or thiourea, and aldehydes [J].
Huang, SL ;
Pan, YJ ;
Zhu, WL ;
Wu, AX .
ORGANIC LETTERS, 2005, 7 (17) :3797-3799
[10]  
JOSHI KC, 1988, J INDIAN CHEM SOC, V65, P202