Environmentally green syntheses of Biginelli compounds, some fused and spiro-fused analogues and bis(indolyl)methanes

被引:0
作者
Patra, Amarendra [1 ]
Mahapatra, Tanusri [1 ]
机构
[1] Univ Calcutta, Dept Chem, Univ Coll Sci & Technol, Kolkata 700009, India
关键词
One-pot synthesis; dihydropyrimidinones; fused and spiro analogues; bis(indolyl)methanes; Aliquat (R) 336; ammonium sulphate; ONE-POT SYNTHESIS; POTASSIUM HYDROGEN SULFATE; CALCIUM-CHANNEL BLOCKERS; SOLVENT-FREE SYNTHESIS; EFFICIENT SYNTHESIS; CATALYZED-REACTIONS; CARBONYL-COMPOUNDS; IONIC LIQUID; CONDENSATION REACTION; RECYCLABLE CATALYST;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
One-pot synthesis of various known and new 3,4-dihydropyrimidin-2(1H)-ones/thiones, 5-oxooctahydroquinazolin-2-ones/thiones and spiro-fused heterocycles are reported using Aliquat (R) 336 as a phase-transfer catalyst under microwave irradiation in water. This new method provides comparatively better catalyst for both Biginelli and Biginelli-like cyclocondensation, greener and milder reaction conditions, quicker reaction, simpler isolation of products and better yields. Catalysing efficiency of Aliquat (R) 336 in conjunction with (NH4)(2)SO4 was also tested for one pot two-component condensation of aldehydes and indole yielding various bis(indolyl)methanes in excellent yield under conventional heating.
引用
收藏
页码:1151 / 1161
页数:11
相关论文
共 85 条
[1]   Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses [J].
Abelman, MM ;
Smith, SC ;
James, DR .
TETRAHEDRON LETTERS, 2003, 44 (24) :4559-4562
[2]   An improved synthesis of Biginelli-type compounds via phase-transfer catalysis [J].
Ahmed, Bahar ;
Khan, Riaz A. ;
Habibullah ;
Keshari, Manoj .
TETRAHEDRON LETTERS, 2009, 50 (24) :2889-2892
[3]   Tangstophosphoric acid (H3PW12O40):: An efficient and eco-friendly catalyst for the one-pot synthesis of dihydropyrimidin-2(1H)-ones [J].
Amini, Mostafa Mohammadpour ;
Shaabani, Ahmad ;
Bazgir, Ayoob .
CATALYSIS COMMUNICATIONS, 2006, 7 (11) :843-847
[4]  
[Anonymous], 1996, CHEM INDOLES
[5]  
ATWAL KS, 1987, HETEROCYCLES, V26, P1189
[6]   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
[7]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .2. 3-SUBSTITUTED-4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
KIMBALL, SD ;
FLOYD, DM ;
MORELAND, S ;
SWANSON, BN ;
GOUGOUTAS, JZ ;
SCHWARTZ, J ;
SMILLIE, KM ;
MALLEY, MF .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2629-2635
[8]   SUBSTITUTED 1,4-DIHYDROPYRIMIDINES .3. SYNTHESIS OF SELECTIVELY FUNCTIONALIZED 2-HETERO-1,4-DIHYDROPYRIMIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
OREILLY, BC ;
SCHWARTZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5898-5907
[9]   A convenient method of synthesis of bis-indolylmethanes:: Indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases. [J].
Babu, G ;
Sridhar, N ;
Perumal, PT .
SYNTHETIC COMMUNICATIONS, 2000, 30 (09) :1609-1614
[10]  
Balasubramanian M., 1996, COMPREHENSIVE HETERO, V5, P245, DOI 10.1016/B978-008096518-5.00109