TRIAZOLINES .25. 1,3-CYCLOADDITION OF ARYL AZIDES TO ENAMIDES AND THE SYNTHESIS OF 1-ARYL-5-AMIDO-1,2,3-TRIAZOLINES

被引：27

作者：

KADABA, PK

机构：

[1] Division of Medicinal Chemistry and Pharmaceutics, College of Pharmacy, A. B. Chandler Medical Center, University of Kentucky, Lexington

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 11期

关键词：

D O I：

10.1021/jo00037a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes for the first tune the 1,3-dipolar cycloaddition of aryl azides to the vinylic bond of enamides, represented by the N-vinyllactam N-vinyl-2-pyrrolidinone (NVP) (Ia) and the open-chain enamide, N-methyl-N-vinylacetamide (NVA) (Ib). Mecharustically, enamides react like enamines in azide cycloaddition reactions to yield 1-aryl-5-amido-1,2,3-triazolines (II).

引用

页码：3075 / 3078

页数：4

共 30 条

[1]

[Anonymous], 1 3 DIPOLAR CYCLOADD

[2] C-13-NMR SPECTRA OF PHENYL-SUBSTITUTED AZOLES - CONFORMATIONAL STUDY [J].

BEGTRUP, M .

ACTA CHEMICA SCANDINAVICA, 1973, 27 (08) :3101-3110

[3]

BOURGOIS J, 1976, B SOC CHIM FR II-CH, P2025

[4] DIRECTIVE EFFECTS IN AROMATIC SUBSTITUTION .30. ELECTROPHILIC SUBSTITUENT CONSTANTS [J].

BROWN, HC ;

OKAMOTO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (18) :4979-4987

[5] ACID-CATALYZED HYDROLYSIS OF N-VINYLACETAMIDES (ENAMIDES) - SUBSTITUENT EFFECTS OF THE ACETAMIDO-GROUPS AND AMINO-GROUPS AND LINEAR FREE-ENERGY CORRELATIONS OF CYCLOHEXENE REACTIVITIES [J].

CSIZMADIA, VM ;

KOSHY, KM ;

LAU, KCM ;

MCCLELLAND, RA ;

NOWLAN, VJ ;

TIDWELL, TT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (04) :974-979

[6] SOME 1-ARYL 1,2,3-TRIAZOLES [J].

ELKHADEM, H ;

MANSOUR, HAR ;

MESHREKI, MH .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (11) :1329-&

[7]

FERUTTI P, 1967, GAZZ CHIM ITAL, V97, P109

[8] VERSUCHE IM ENAMINGEBIET, .7. REAKTIONEN VON ARYLSULFONYLAZIDEN MIT ENAMINEN AUS KETOMETHYLENVERBINDUNGEN [J].

FUSCO, R ;

BIANCHETTI, G ;

UGO, R ;

POCAR, D .

CHEMISCHE BERICHTE-RECUEIL, 1963, 96 (03) :802-&

[9]

Fusco R., 1962, GAZZ CHIM ITAL, V92, P1040

[10]

Gilchrist T. L., 1974, ADV HETEROCYCLIC CHE, P33

← 1 2 3 →