γ-spiroiminolactone synthesis by reaction of acetylenic esters and α-dicarbonyl compounds in the presence of aryl isocyanide

被引：23

作者：

Maghsoodlou, MT ^{[1
]}

Hazeri, N ^{[1
]}

Habibi-Khorasani, SM ^{[1
]}

Marandi, G ^{[1
]}

Nassiri, M ^{[1
]}

机构：

[1] Univ Sistan & Baluchestan, Dept Chem, Zahedan, Iran

来源：

SYNTHETIC COMMUNICATIONS | 2005年 / 35卷 / 21期

关键词：

acetylenic esters; alpha-dicarbonyl compounds; iminolactones; isocyanides; three-component reaction;

D O I：

10.1080/00397910500290359

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The highly reactive 1:1 intermediate produced in the reaction of aryl isocyanides and acetylenic esters was trapped by the alpha-dicarbonyl compounds to yield gamma-spiroiminolactone derivatives in good yields.

引用

页码：2771 / 2777

页数：7

共 13 条

[1] ADDITIONS TO TERNARY COMPOUNDS .22. THERMODYNAMICALLY CONTROLLED ADDUCT FROM TERT-BUTYLISONITRILE AND ACETYLENECARBOXYLATE [J].

DILLINGER, HJ ;

FENGLER, G ;

SCHUMANN, D ;

WINTERFELDT, E .

TETRAHEDRON, 1974, 30 (15) :2561-2564

[2]

GRIECO PA, 1975, SYNTHESIS-STUTTGART, V2, P67

[3] Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes [J].

Nair, V ;

Rajesh, C ;

Vinod, AU ;

Bindu, S ;

Sreekanth, AR ;

Mathen, JS ;

Balagopal, L .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (12) :899-907

[4] A novel synthesis of 2-aminopyrroles using a three-component reaction [J].

Nair, V ;

Vinod, AU ;

Rajesh, C .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4427-4429

[5] The reaction of cyclohexyl isocyanide and dimethyl acetylenedicarboxylate with aldehydes: a novel synthesis of 2-aminofuran derivatives [J].

Nair, V ;

Vinod, AU .

CHEMICAL COMMUNICATIONS, 2000, (12) :1019-1020

[6] REACTIONS OF ISOCYANIDES WITH ACTIVATED ACETYLENES IN PROTIC SOLVENTS [J].

OAKES, TR ;

DONOVAN, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (07) :1319-1325

[7] SMALL RING SYSTEMS FORM ISOCYANIDES .I. REACTION OF ISOCYANIDES WITH HEXAFLUOROBUTYNE-2 [J].

OAKES, TR ;

DAVID, HG ;

NAGEL, FJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (17) :4761-&

[8]

Oliaruso M.A., 1993, SYNTHESIS LACTONES L

[9]

Takizawz T., 1969, TETRAHEDRON LETT, V10, P3407

[10] FROM ISOCYANIDES VIA 4-COMPONENT CONDENSATIONS TO ANTIBIOTIC SYNTHESES [J].

UGI, I .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1982, 21 (11) :810-819

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