Sulfonic Acid Functionalized Silica: A Mild, Reusable and Efficient Heterogeneous Catalyst for the Highly Diastereoselective Synthesis of cis-Isoquinolonic Acids

被引：16

作者：

Karimi, Ali Reza ^{[1
]}

Pashazadeh, Rahim ^{[1
]}

机构：

[1] Arak Univ, Dept Chem, Arak 38156, Iran

来源：

SYNTHESIS-STUTTGART | 2010年 / 03期

关键词：

sulfonic acid functionalized silica; cis-isoquinolonic acids; diastereoselective synthesis; three-component reaction; ONE-POT SYNTHESIS; RECOVERABLE INTERPHASE CATALYST; HOMOPHTHALIC ANHYDRIDE; 3-COMPONENT REACTION; RECYCLABLE CATALYST; CARBONYL-COMPOUNDS; SOLID ACIDS; IMINES; AMINES; KAL(SO4)(2)CENTER-DOT-12H(2)O;

D O I：

10.1055/s-0029-1218595

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfonic acid functionalized silica (SAFS) is found to be a recyclable heterogeneous catalyst for the rapid and efficient synthesis of various cis-isoquinolonic acids from the three-component condensation reaction of homophthalic anhydride, an amine, and an aldehyde. This reaction was highly diastereoselective and only one diastereomer was obtained in all cases.

引用

收藏

页码：437 / 442

页数：6

相关论文

共 27 条

[1] A stereoselective three-component reaction:: KAl(SO4)2•12H2O, an efficient and reusable catalyst for the one-pot synthesis of cis-isoquinolonic acids [J].

Azizian, J ;

Mohammadi, AA ;

Karimi, AR ;

Mohammadizadeh, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :350-352

[2] SYNTHESIS OF NOVEL ISOQUINOLINE DERIVATIVES AS POTENTIAL CNS-AGENTS [J].

BONNAUD, B ;

CARLESSI, A ;

BIGG, DCH .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (01) :257-265

[3] Organic reactions catalyzed over solid acids [J].

Corma, A ;

Garcia, H .

CATALYSIS TODAY, 1997, 38 (03) :257-308

[4] INORGANIC SOLID ACIDS AND THEIR USE IN ACID-CATALYZED HYDROCARBON REACTIONS [J].

CORMA, A .

CHEMICAL REVIEWS, 1995, 95 (03) :559-614

[5] A STUDY AND MECHANISTIC INTERPRETATION OF THE ELECTRONIC AND STERIC EFFECTS THAT DETERMINE THE STEREOCHEMICAL OUTCOME OF THE REACTION OF SCHIFF-BASES WITH HOMOPHTHALIC ANHYDRIDE AND 3-PHENYLSUCCINIC ANHYDRIDE [J].

CUSHMAN, M ;

MADAJ, EJ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :907-915

[6] TOTAL SYNTHESIS OF NITIDINE CHLORIDE [J].

CUSHMAN, M ;

CHENG, L .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) :286-288

[7]

CUSHMAN M, 1977, J ORG CHEM, V42, P1111, DOI 10.1021/jo00427a001

[8] UTILIZATION OF THE 1-FERROCENYL-2-METHYLPROPYL SUBSTITUENT AS A CHIRAL AUXILIARY IN THE ASYMMETRIC SYNTHESES OF THE BENZOPHENANTHRIDINE ALKALOIDS (+)-CORYNOLINE AND (-)-CORYNOLINE [J].

CUSHMAN, M ;

CHEN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1517-1521

[9] Sulfonic acid functionalized silica:: A remarkably efficient heterogeneous reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide [J].

Das, B ;

Venkateswarlu, K ;

Holla, H ;

Krishnaiah, M .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 253 (1-2) :107-111

[10] An efficient, rapid and regioselective nuclear bromination of aromatics and heteroaromatics with NBS using sulfonic-acid-functionalized silica as a heterogeneous recyclable catalyst [J].

Das, Biswanath ;

Venkateswarlu, Katta ;

Krishnaiah, Maddeboina ;

Holla, Harish .

TETRAHEDRON LETTERS, 2006, 47 (49) :8693-8697