A stereoselective three-component reaction:: One-pot synthesis of cis-isoquinolonic acids catalyzed by silica sulfuric acid under mild and heterogeneous conditions

被引：27

作者：

Azizian, J ^{[1
]}

Mohammadi, AA ^{[1
]}

Soleimani, E ^{[1
]}

Karimi, AR ^{[1
]}

Mohammadizadeh, MR ^{[1
]}

机构：

[1] Shahid Beheshti Univ, Fac Sci, Dept Chem, Tehran, Iran

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2006年 / 43卷 / 01期

关键词：

D O I：

10.1002/jhet.5570430129

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and stereoselective three-component one-step synthesis of cis-isoquinolonic acid using silica sulfuric acid as a heterogeneous catalyst from an aldehyde, amine and homophthalic anhydride in acetonitrile is described. This new method produces pure products in high yields (81-91%).

引用

页码：187 / 190

页数：4

共 28 条

[11] TOTAL SYNTHESIS OF (+/-)-14-EPICORYNOLINE, (+/-)-CORYNOLINE, AND (+)-6-OXOCORYNOLINE [J].

CUSHMAN, M ;

ABBASPOUR, A ;

GUPTA, YP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2873-2879

[12] HIGHLY STEREOSELECTIVE SYNTHESIS OF 3,4-DIHYDRO-1(2H)-ISOQUINOLINONES AND 8-OXOBERBINES FROM HOMOPHTHALIC ANHYDRIDES AND AZOMETHINES [J].

HAIMOVA, MA ;

MOLLOV, NM ;

IVANOVA, SC ;

DIMITROVA, AI ;

OGNYANOV, VI .

TETRAHEDRON, 1977, 33 (03) :331-336

[13] 2,4-DIAMINO-5-BENZYLPYRIMIDINES AND ANALOGS AS ANTIBACTERIAL AGENTS .12. 1,2-DIHYDROQUINOLYLMETHYL ANALOGS WITH HIGH-ACTIVITY AND SPECIFICITY FOR BACTERIAL DIHYDROFOLATE-REDUCTASE [J].

JOHNSON, JV ;

RAUCKMAN, BS ;

BACCANARI, DP ;

ROTH, B .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) :1942-1949

[14]

KHODAEI MM, 2004, POLISH J CHEM, V3, P387

[15] Efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones over silica sulfuric acid as a reusable catalyst under solvent-free conditions [J].

Salehi, P ;

Dabiri, M ;

Zolfigol, MA ;

Ali, M ;

Fard, B .

HETEROCYCLES, 2003, 60 (11) :2435-2440

[16] Oxidative coupling of thiols in solution and under solvent-free conditions [J].

Shirini, F ;

Zolfigol, MA ;

Khaleghi, M .

MENDELEEV COMMUNICATIONS, 2004, 14 (01) :34-35

[17]

Shirini F, 2004, B KOREAN CHEM SOC, V25, P325

[18]

STANOYEVA ER, 1984, KHIM GETEROTSIKL+, P1587

[19] New trans/cis tetrahydroisoquinolines.: 2.: trans- and cis-3-(1-methyl-1H-pyrrol-2-yl)-1-(2H)-oxo-2-phenethyl-1,2,3,4-tetrahydroisoquinolin-4-carboxylic acids and subsequent transformations [J].

Stoyanova, MP ;

Kozekov, ID ;

Palamareva, MD .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (05) :795-803

[20] One-pot synthesis of cis-isoquinolonic acid derivatives via three-component reaction of homophthalic anhydride with aldehydes and amines using ytterbium(III) triflate as catalyst [J].

Wang, LM ;

Liu, JJ ;

Tian, H ;

Qian, CT ;

Sun, J .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (05) :689-694

← 1 2 3 →