A novel microwave-assisted one-pot synthesis of pyrano[2,3-d]pyrimidines and pyrido[2,,3-d]pyrimidines via a three component reaction in solvent-free condition

被引:37
作者
Devi, I [1 ]
Bhuyan, PJ [1 ]
机构
[1] Reg Res Lab, Div Med Chem, Jorhat 785006, Assam, India
关键词
solvent-free reaction; multicomponent reaction; microwave-assisted reaction; pyrano[2,3-d]pyrimidines; pyrido[2,3-d]pyrimidines;
D O I
10.1055/s-2003-43367
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three-component cyclocondensation of barbituric acids 1, triethylorthoformate. 2 and alkyl nitriles 3 in presence of acetic anhydride proceeds under microwave-assisted conditions to give pyrano[2,3-d]pyrimidines 4 in excellent yields. 6-Aminouracils 5 or 6-hydroxy-aminouracils 7 react with 2 and 3 under identical conditions to yield pyrido[2,3-d]pyrimidines 6 or pyrido[2,3-d]pyrimidine oxides 8 in high yields.
引用
收藏
页码:283 / 286
页数:4
相关论文
共 49 条
[1]  
AHLUWALIA VK, 1990, HETEROCYCLES, V31, P129
[2]  
AHLUWALIA VK, 1990, INDIAN J CHEM B, V29, P1141
[3]   A CONVENIENT SYNTHESIS OF 1,3-DIARYL-1,2,3,4,-TETRAHYDRO-5,7,7-TRIMETHYL-4-OXO-2-THIOXO-7H-PYRANO[2,3-D]PYRIMIDINES [J].
AHLUWALIA, VK ;
KUMAR, R ;
KHURANA, A ;
BHATLA, R .
TETRAHEDRON, 1990, 46 (11) :3953-3962
[4]   A NOVEL ONE-STEP SYNTHESIS OF PYRANO(2,3-D) PYRIMIDINES [J].
AHLUWALIA, VK ;
SHARMA, HR ;
TYAGI, R .
TETRAHEDRON, 1986, 42 (14) :4045-4048
[5]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[6]  
2-E
[7]   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
[8]   A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines [J].
Bagley, MC ;
Dale, JW ;
Bower, J .
CHEMICAL COMMUNICATIONS, 2002, (16) :1682-1683
[9]   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
[10]   A novel metal iodide promoted three-component synthesis of substituted pyrrolidines [J].
Bertozzi, F ;
Gustafsson, M ;
Olsson, R .
ORGANIC LETTERS, 2002, 4 (18) :3147-3150