An Efficient Biginelli One-Pot Synthesis of New Benzoxazole-Substituted Dihydropyrimidinones and Thiones Catalysed by Alumina-Supported Trifluoromethane Sulfonic Acid Under Solvent Free Conditions

被引：16

作者：

Arjun, M. ^{[2
]}

Sridhar, D. ^{[2
]}

Chari, M. Adharvana ^{[3
]}

Sarangapani, M. ^{[1
]}

机构：

[1] Kakatiya Univ, Dept Chem, Warangal 506009, Andhra Pradesh, India

[2] Kakatiya Univ, Univ Coll Pharmaceut Sci, Warangal 506009, Andhra Pradesh, India

[3] Kyung Hee Univ, Dept Appl Chem, Seoul, South Korea

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2009年 / 46卷 / 01期

关键词：

CALCIUM-CHANNEL BLOCKERS; HIGH-YIELD SYNTHESIS; ANTIHYPERTENSIVE AGENTS; HETEROGENEOUS CATALYST; MICROWAVE IRRADIATION; SILICA; ESTERS; DERIVATIVES; PYRIMIDINES; PROTOCOL;

D O I：

10.1002/jhet.29

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of benzoxazole-substituted 3,4-dihydropyrimidinones (DHPMs) using alumina supported trifluoromethane sulfonic acid as the catalyst for the first time from an aldehyde, P-keto ester, and benzoxazole-substituted urea and thiourea under solvent-free conditions is described. When compared with the classical Biginelli reaction conditions, this new method consistently has the advantage of excellent yields (80-93%) and short reaction time (30-120 Minutes) at 120 degrees C temperature.

引用

页码：119 / 123

页数：5

共 37 条

[21] A new approach to N-3 functionalized 3,4-dihydropyrimidine-2(1H)-ones with 1,2,4-oxadiazole group as amide isostere via ionic liquid-phase technology [J].

Legeay, Jean Christophe ;

Vanden Eynde, Jean Jacques ;

Bazureau, Jean Pierre .

TETRAHEDRON LETTERS, 2007, 48 (06) :1063-1068

[22] Cadmium chloride:: An efficient catalyst for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones [J].

Narsaiah, AV ;

Basak, AK ;

Nagaiah, K .

SYNTHESIS-STUTTGART, 2004, (08) :1253-1256

[23]

Nishiguchi T., 1989, J CHEM SOC PERK T, V1, P707

[24]

OREILLY BC, 1987, HETEROCYCLES, V26, P1185

[25] Synthesis and antimicrobial activity of some novel 2,5- and/or 6-substituted benzoxazole and benzimidazole derivatives [J].

Ören, I ;

Temiz, Ö ;

Yalçin, I ;

Sener, E ;

Altanlar, N .

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 1999, 7 (02) :153-160

[26] NOVEL ALKALOIDS FROM THE SPONGE BATZELLA SP - INHIBITORS OF HIV GP120-HUMAN CD4 BINDING [J].

PATIL, AD ;

KUMAR, NV ;

KOKKE, WC ;

BEAN, MF ;

FREYER, AJ ;

DEBROSSE, C ;

MAI, S ;

TRUNEH, A ;

FAULKNER, DJ ;

CARTE, B ;

BREEN, AL ;

HERTZBERG, RP ;

JOHNSON, RK ;

WESTLEY, JW ;

POTTS, BCM .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1182-1188

[27] AN ENANTIOSPECIFIC SYNTHESIS OF THE TRICYCLIC GUANIDINE SEGMENT OF THE ANTI-HIV MARINE ALKALOID BATZELLADINE-A [J].

RAO, AVR ;

GURJAR, MK ;

VASUDEVAN, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) :1369-1370

[28] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .4. BASIC 3-SUBSTITUTED-4-ARYL-1,4-DIHYDROPYRIMIDINE-5-CARBOXYLIC ACID-ESTERS - POTENT ANTIHYPERTENSIVE AGENTS [J].

ROVNYAK, GC ;

ATWAL, KS ;

HEDBERG, A ;

KIMBALL, SD ;

MORELAND, S ;

GOUGOUTAS, JZ ;

OREILLY, BC ;

SCHWARTZ, J ;

MALLEY, MF .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (17) :3254-3263

[29]

Safak C, 1996, PHARMAZIE, V51, P180

[30] A new convenient synthesis of 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones/ones [J].

Shutalev, AD ;

Kishko, EA ;

Sivova, NV ;

Kuznetsov, AY .

MOLECULES, 1998, 3 (03) :100-106

← 1 2 3 4 →