Synthesis of 2-thioxoimidazolin-4-one andthiazolo[3,2-a]-benzimidazole derivatives from substituted maleimides

被引：11

作者：

Bentarzi, Yamina ^{[1
,2
]}

Nedjar-Kolli, Bellara ^{[1
]}

Plas, Aurelie ^{[3
]}

Chalard, Pierre ^{[3
]}

Troin, Yves ^{[3
]}

机构：

[1] Univ Sci & Tech Houari Boumediene, Lab Chim Organ Appl, BP 3, Bab Ezzouar 16111, Alger, Algeria

[2] Ctr Rech Sci Tech Analyse Physicochim CRAPC, Alger RP 16004, Algeria

[3] Clermont Univ, ENSCCF, EA 987, LCHG, F-63000 Clermont Ferrand, France

来源：

ARKIVOC | 2010年

关键词：

Thioxoimidazolin-4-one; hetero Michael reaction; thiazolobenzimidazoles; maleimide; PHASE SYNTHESIS;

D O I：

10.3998/ark.5550190.0011.a27

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe here a hetero Michael-type reaction, involving maleimides and 2-cyanoacetichydrazide or 2-mercaptobenzimidazole, followed by an opening cyclization reaction with isothiocyanates. This reaction allows the preparation of new 2-thioxoimidazolidin-4-one and thiazolo[3,2-a]benzimidazole derivatives depending on the nucleophile used.

引用

页码：328 / 337

页数：10

共 28 条

[1] THIAZOLO[3.2-ALPHA]BENZIMIDAZOLES [J].

ALPER, AE ;

TAURINS, A .

CANADIAN JOURNAL OF CHEMISTRY, 1967, 45 (23) :2903-&

[2] Antimicrobial activities of some tetrahydronaphthalene-benzimidazole derivatives [J].

Ates-Alagoz, Zeynep ;

Yildiz, Sulhiye ;

Buyukbingo, Erdem .

CHEMOTHERAPY, 2007, 53 (02) :110-113

[3] A versatile method for the synthesis of substituted 1-aminohydantoin derivatives [J].

Bélai, I .

TETRAHEDRON LETTERS, 2003, 44 (40) :7475-7477

[4]

Binet J., 2004, PCT Int. Appl., Patent No. [WO2004031160 A3, 2004031160]

[5] Utility of cyanoacetic acid hydrazide in heterocyclic synthesis [J].

Bondock, Samir ;

Tarhoni, Abd El-Gaber ;

Fadda, Ahmed A. .

ARKIVOC, 2006, :113-156

[6] Practical synthesis of functionalized 2-thioxoimidazolidine derivatives [J].

Bouzroura, Samia ;

Hammal, Lamouri ;

Nedjar-Kolli, Bellara ;

Balegroune, Fadila ;

Hamadene, Malika ;

Poulain, Sophie .

SYNTHETIC COMMUNICATIONS, 2008, 38 (03) :448-455

[7] A practical and eco-friendly synthesis of stereocontrolled alkylaminomethylidene derivatives of 2-thiohydantoins by dimethylamine substitution [J].

Chérouvrier, JR ;

Carreaux, F ;

Bazureau, JP .

TETRAHEDRON LETTERS, 2002, 43 (48) :8745-8749

[8]

CLAUSSNER A, 2009, Patent No. 200109090

[9] N-hetaryl-2-cyanoacetamides in the synthesis of substituted (E)-N-hetaryl-2-cyanoacrylamides, (E)-N-alkyl-N-hetaryl-2-cyanoacrylamides, and 6-amino-2-oxo-4-phenyl-1-(pyridin-2-yl)-1,2-dihydropyridine-3,5-dicarbonitriles [J].

Dyachenko, I. V. ;

Dyachenko, V. D. ;

Rusanov, E. B. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (01) :83-89

[10]

Fadda AA, 2008, TURK J CHEM, V32, P259

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