Synthesis of 2,3-dihydroimidazo[ 1,2-b]isoquinoline-5(1H)-one and derivatives

被引：11

作者：

Bollini, M ^{[1
]}

Asís, SE ^{[1
]}

Bruno, AM ^{[1
]}

机构：

[1] Univ Buenos Aires, Ctr Sintesis & Estudio Nuevos Compuestos Antineop, Dept Quim Organ, Fac Farm & Bioquim, RA-1113 Buenos Aires, DF, Argentina

来源：

SYNTHESIS-STUTTGART | 2006年 / 02期

关键词：

acylation; DMAP; isomerizations; heterocycles; microwave synthesis;

D O I：

10.1055/s-2005-918505

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

A novel and efficient synthesis of 2,3-dihydroimidazo[1,2-b]isoquinoline-5(1H)-one by inicrowave irradiation is reported. Several new derivatives of 2,3-dihydroinlidazo[1,2-b]-lisoquinoline-5(1H)-one have been synthesized by acylation using DMAP as catalyst. A kinetic study employing HPLC allowed the determination of the N- and C-acylated isomers formed.

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收藏

页码：237 / 242

页数：6

相关论文

共 13 条

[1]

Synthesis and biological evaluation of substituted quinolines:: Potential treatment of protozoal and retroviral co-infections [J].

Fakhfakh, MA ;

Fournet, A ;

Prina, E ;

Mouscadet, JF ;

Franck, X ;

Hocquemiller, R ;

Figadère, B .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (23) :5013-5023

[2]

ACETYLPYRIDINIUM ION INTERMEDIATE IN PYRIDINE-CATALYZED HYDROLYSIS AND ACYL TRANSFER REACTIONS OF ACETIC ANHYDRIDE - OBSERVATION, KINETICS, STRUCTURE-REACTIVITY CORRELATIONS, AND EFFECTS OF CONCENTRATED SALT SOLUTIONS [J].

FERSHT, AR ;

JENCKS, WP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5432-&

[3]

HETEROCYCLES DERIVED FROM CONDENSATION OF HOMOPHTHALIC ANHYDRIDE WITH ETHYLENEDIAMINE [J].

GRINBERG, H ;

LAMDAN, S ;

GAOZZA, CH .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1976, 8 (06) :287-292

[4]

HOEFLE G, 1978, ANGEW CHEM INT EDIT, V17, P569

[5]

Controlled microwave heating in modern organic synthesis [J].

Kappe, CO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6250-6284

[6]

KAZUO K, 1979, CHEM PHARM BULL, V27, P2372

[7]

Selective monoacylation of a diamine using intramolecular delivery by a DMAP unit [J].

Kelly, TR ;

Cavero, M .

ORGANIC LETTERS, 2002, 4 (16) :2653-2656

[8]

Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: Dual activation of the electrophile and the nucleophile [J].

Mermerian, AH ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4050-4051

[9]

Murugan R, 2003, ALDRICHIM ACTA, V36, P21

[10]

CONDENSED HETEROTRICYCLES - SYNTHESIS AND REACTIONS OF B-FUSED 1(2H)-ISOQUINOLINONES WITH UNUSUAL ENAMINIC PROPERTIES [J].

NAGARAJAN, K ;

RAO, VR ;

SHAH, RK ;

SHENOY, SJ ;

FRITZ, H ;

RICHTER, WJ ;

MULLER, D .

HELVETICA CHIMICA ACTA, 1988, 71 (01) :77-92