An expedient method for the synthesis of 6-substituted uracils under microwave irradiation in a solvent-free medium

被引:68
作者
Devi, I [1 ]
Bhuyan, PJ [1 ]
机构
[1] Reg Res Lab, Div Med Chem, Jorhat 785006, Assam, India
关键词
microwave-assisted reactions; 6-hydroxy-uracils; 6-amino-uracils; solvent-free medium;
D O I
10.1016/j.tetlet.2005.06.075
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Condensation of malonic acid I and ureas 2a-f proceeds smoothly in the presence of acetic anhydride 3 under microwave irradiation in solvent-free conditions to give 6-hydroxy-uracils 4 in excellent yields. Under identical conditions, the condensation of cyanoacetic acid 5 and ureas 2a,b,g and h in the presence of acetic anhydride 3, followed by cyclization in the presence of sodium hydroxide affords 6-amino-uracils 6 in high yields. The work-up procedures are simple and products need no purification. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5727 / 5729
页数:3
相关论文
共 32 条
[1]
Concerning alkali and acyl barbituric acids. [J].
Biltz, H ;
Wittek, H .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1921, 54 :1035-1058
[2]
REACTIONS OF 1,3-DIMETHYL-5,6-DIAMINOURACIL [J].
BLICKE, FF ;
GODT, HC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (10) :2798-2800
[3]
Bobranski B., 1977, WIAD CHEM, V31, P231
[4]
RECENT PROGRESS IN BARBITURIC-ACID CHEMISTRY [J].
BOJARSKI, JT ;
MOKROSZ, JL ;
BARTON, HJ ;
PALUCHOWSKA, MH .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1985, 38 :229-297
[5]
Brown D. J., 1984, Comprehensive Heterocyclic Chemistry, V1, P57
[6]
CLARKLEWIS JW, 1959, J CHEM SOC, P1628
[7]
Cossy J, 2002, SYNTHESIS-STUTTGART, P951
[8]
Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions [J].
Devi, I ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2004, 45 (47) :8625-8627
[9]
Studies on uracils:: a facile one-pot synthesis of oxazino[4,5-d]-, pyrano[2,3-d]-, pyrido[2,3-d]- and pyrimido[4,5-d]pyrimidines using microwave irradiation in the solid state [J].
Devi, I ;
Borah, HN ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2004, 45 (11) :2405-2408
[10]
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 [J].
Devi, I ;
Bhuyan, PJ .
SYNLETT, 2004, (02) :283-286