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

来源：

JOURNAL OF THE INDIAN CHEMICAL SOCIETY | 2014年 / 91卷 / 06期

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

页码：1151 / 1161

页数：11

共 85 条

[21] Synthesis and antibacterial evaluation of certain quinolone derivatives [J].

Chen, YL ;

Fang, KC ;

Sheu, JY ;

Hsu, SL ;

Tzeng, CC .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) :2374-2377

[22] Synthesis and in vitro microbiological evaluation of novel 4-aryl-5-isopropoxycarbonyl-6-methyl-3,4-dihydropyrimidinones [J].

Chitra, S. ;

Devanathan, D. ;

Pandiarajan, K. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) :367-371

[23] NON-STEROIDAL ANTIINFLAMMATORY AGENTS .1. SYNTHESIS OF 4-HYDROXY-2-OXO-1,2-DIHYDROQUINOLIN-3-YL ALKANOIC ACIDS BY THE WITTIG REACTION OF QUINISATINES [J].

FABER, K ;

STUCKLER, H ;

KAPPE, T .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) :1177-1181

[24] Researches on pyrimidines CXXX Synthesis of 2-keto-1,2,3,4-tetrahydropyrimidines [J].

Folkers, K ;

Harwood, HJ ;

Johnson, TB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1932, 54 :3751-3758

[25] STEREOCONTROLLED SYNTHESIS OF (-)-HAPALINDOLE-G [J].

FUKUYAMA, T ;

CHEN, XQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3125-3126

[26] Facile and Mild Synthesis of bis(3-Indolyl)methanes [J].

Ghorbani-Vaghei, R. ;

Malaekehpoor, S. M. .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2010, 42 (02) :175-182

[27] A practical and efficient synthesis of bis(indolyl)methanes in water, and synthesis of di-, tri-, and tetra(bis-indolyl)methanes under thermal conditions catalyzed by oxalic acid dihydrate [J].

Ghorbani-Vaghei, Ramin ;

Veisi, Hojat ;

Keypour, Hassan ;

Dehghani-Firouzabadi, Ahmad Ali .

MOLECULAR DIVERSITY, 2010, 14 (01) :87-96

[28]

GUPTA R, 1995, INDIAN J CHEM B, V34, P151

[29] A solvent-free protocol for facile condensation of indoles with carbonyl compounds using silica chloride as a new, highly efficient, and mild catalyst [J].

Hasaninejad, Alireza ;

Zare, Abdolkarim ;

Sharghi, Hashem ;

Shekouhy, Mohsen ;

Khalifeh, Reza ;

Beni, Alireza Salimi ;

Zare, Ahmad Reza Moosavi .

CANADIAN JOURNAL OF CHEMISTRY, 2007, 85 (06) :416-420

[30] Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones [J].

Hu, EH ;

Sidler, DR ;

Dolling, UH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3454-3457

← 1 2 3 4 5 6 7 8 9 →