Efficient synthesis of novel heterocyclic dihydropyrimidine-2,4,5(3H)-trione and tetrahydro-2-thioxopyrimidine-4,5-dione derivatives

被引:2
作者
Mehrabi, Hossein [1 ]
Alizadeh-bami, Farzaneh [1 ]
机构
[1] Vali E Asr Univ Rafsanjan, Dept Chem, Rafsanjan 77176, Iran
关键词
Dihydropyrimidine-2,4,5(3H)-triones; Tetrahydro-2-thioxopyrimidine-4,5-dione; Three-component reaction; Phenyl isocyanate; Phenyl isothiocyanate; Ethyl bromopyruvate; METHANOL; ACID;
D O I
10.1007/s13738-015-0591-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel heterocyclic dihydropyrimidine-2,4,5(3H)-triones and tetrahydro-2-thioxopyrimidine-4,5-diones were synthesized via three-component reaction between appropriate amines, phenyl isocyanate or phenyl isothiocyanate, and ethyl bromopyruvate in DMF under reflux conditions without using additional bases or catalysts. All the products were obtained in good yield by simple and efficient procedure. The structures of all the synthesized compounds were established from advanced spectroscopic data.
引用
收藏
页码:1275 / 1279
页数:5
相关论文
共 9 条
[1]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .3. 3-CARBAMOYL-4-ARYL-1,2,3,4-TETRAHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS ORALLY EFFECTIVE ANTIHYPERTENSIVE AGENTS [J].
ATWAL, KS ;
SWANSON, BN ;
UNGER, SE ;
FLOYD, DM ;
MORELAND, S ;
HEDBERG, A ;
OREILLY, BC .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :806-811
[2]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[3]   DIHYDROPYRIMIDINES - NOVEL CALCIUM-ANTAGONISTS WITH POTENT AND LONG-LASTING VASODILATIVE AND ANTIHYPERTENSIVE ACTIVITY [J].
CHO, H ;
UEDA, M ;
SHIMA, K ;
MIZUNO, A ;
HAYASHIMATSU, M ;
OHNAKA, Y ;
TAKEUCHI, Y ;
HAMAGUCHI, M ;
AISAKA, K ;
HIDAKA, T ;
KAWAI, M ;
TAKEDA, M ;
ISHIHARA, T ;
FUNAHASHI, K ;
SATOH, F ;
MORITA, M ;
NOGUCHI, T .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2399-2406
[4]  
KAPPE CO, 1993, TETRAHEDRON, V49, P6937
[5]   (Z)-2-Amino-5-[2,4-dimethoxy-6-(4-methoxystyryl)benzylidene]-1,3-thiazol-4(5H)-one methanol solvate [J].
Madadi, Nikhil Reddy ;
Reddy, Thirupathi Reddy Yerram ;
Penthala, Narsimha Reddy ;
Parkin, Sean ;
Crooks, Peter A. .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 :O1792-U483
[6]  
Penthala N.R., 2011, BREAST CANC CURRENT, P283
[7]   Synthesis of enantiomerically pure 4-aryl-3,4-dihydro-pyrimidin-2(1H)-ones via enzymatic resolution:: preparation of the antihypertensive agent (R)-SQ 32926 [J].
Schnell, B ;
Strauss, UT ;
Verdino, P ;
Faber, K ;
Kappe, CO .
TETRAHEDRON-ASYMMETRY, 2000, 11 (07) :1449-1453
[8]   BIOMIMETIC SYNTHESES OF (+/-)-CRAMBINE-A, CRAMBINE-B, CRAMBINE-C1, AND CRAMBINE-C2 - REVISION OF THE STRUCTURES OF CRAMBINE-B AND CRAMBINE-C1 [J].
SNIDER, BB ;
SHI, ZP .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3828-3839
[9]   An ecofriendly catalytic route for the preparation of perfumery grade methyl anthranilate from anthranilic acid and methanol [J].
Yadav, GD ;
Krishnan, MS .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1998, 2 (02) :86-95