N-SUBSTITUTED PYRROLINONES FROM ENAMINES AND ALPHA-DICARBONYLS

被引：14

作者：

CABALLERO, E

PUEBLA, P

DOMERCQ, M

MEDARDE, M

LOPEZ, JL

SANFELICIANO, A

机构：

[1] Departamento de Química Orgánica, Farmacéutica. Facultad

来源：

TETRAHEDRON | 1994年 / 50卷 / 26期

关键词：

D O I：

10.1016/S0040-4020(01)85268-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction between N-substituted enamines and phenylglyoxal or glyoxal yielded Delta(2)-pyrrolin-5-ones in moderate to good yields. An uncommon pyrrolo [2,1-b]thiazole derivative was formed as a minor product when a N-(2-mercaptoethyl)enamine was used as the starting reagent. An explanation for the regiochemistry of the reaction is proposed.

引用

收藏

页码：7849 / 7856

页数：8

相关论文

共 17 条

[1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[2] FORMATION OF PYRROLINONES AND 2-DIALKYLAMINOFURANS FROM GAMMA-OXOAMIDES [J].

BOYD, GV ;

HEATHERI.K .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (07) :346-&

[3] REGIOCHEMISTRY IN THE SYNTHESIS OF 2,3,8,8A-TETRAHYDRO-7H-OXAZOLO[3,2-A]PYRIDINES [J].

CABALLERO, E ;

PUEBLA, P ;

MEDARDE, M ;

FELICIANO, AS .

TETRAHEDRON, 1993, 49 (44) :10079-10088

[4] THE CHEMISTRY OF BETA-ENAMINONITRILES AS VERSATILE REAGENTS IN HETEROCYCLIC SYNTHESIS [J].

ERIAN, AW .

CHEMICAL REVIEWS, 1993, 93 (06) :1991-2005

[5] FUSED HETEROCYCLES FROM PYRROLETHIOLS [J].

HARRIS, RLN ;

MCFADDEN, HG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (07) :1473-1481

[6]

Katritzky A. R., 1984, COMPREHENSIVE HETERO

[7] SYNTHESIS AND ANTIMICROBIOLOGICAL ACTIVITY OF N-ARYL-SUBSTITUTED 2-METHYL-3-CARBETHOXY-5-PYRROLINONE DERIVATIVES [J].

LOVREN, F ;

GAON, ID ;

BOBAREVIC, B .

ARCHIV DER PHARMAZIE, 1990, 323 (11) :901-904

[8]

LOVREN F, 1992, PHARMAZIE, V47, P773

[9] MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS [J].

MOHAMADI, F ;

RICHARDS, NGJ ;

GUIDA, WC ;

LISKAMP, R ;

LIPTON, M ;

CAUFIELD, C ;

CHANG, G ;

HENDRICKSON, T ;

STILL, WC .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :440-467

[10]

NERSEYAN LA, 1970, ARM KHIM ZH, V23, P741