SYNTHESIS OF AMIDES - AN EFFICIENT AND CHEMOSELECTIVE METHOD FOR THE PREPARATION OF BETA-LACTAM DERIVATIVES RELATED TO HLE INHIBITORS

被引：6

作者：

DIFABIO, R ^{[1
]}

SUMMA, V ^{[1
]}

ROSSI, T ^{[1
]}

机构：

[1] GLAXO RES,I-37100 VERONA,ITALY

来源：

TETRAHEDRON | 1993年 / 49卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(01)80373-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical method for the chemoselective synthesis of amides in presence of the beta-lactam ring has been described, by an efficient coupling reaction between a reactive 2-pyridyl thiolester intermediate and a suitable N-silylamine.

引用

页码：2299 / 2306

页数：8

共 24 条

[1] SYNTHESIS OF NOVEL CEPHEM-4-KETONES - A NEW SERIES OF HUMAN-LEUKOCYTE ELASTASE INHIBITORS [J].

ALPEGIANI, M ;

BISSOLINO, P ;

PERRONE, E ;

CASSINELLI, G ;

FRANCESCHI, G .

TETRAHEDRON LETTERS, 1991, 32 (43) :6207-6210

[2]

CHAUVETTE RR, 1966, J MED CHEM, P741

[3] EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES [J].

COREY, EJ ;

NICOLAOU, KC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5614-5616

[4]

DOHERTY JB, 1986, NATURE, V322, P192, DOI 10.1038/322192a0

[5] INHIBITION OF HUMAN-LEUKOCYTE ELASTASE .1. INHIBITION BY C-7-SUBSTITUTED CEPHALOSPORIN TERT-BUTYL ESTERS [J].

DOHERTY, JB ;

ASHE, BM ;

BARKER, PL ;

BLACKLOCK, TJ ;

BUTCHER, JW ;

CHANDLER, GO ;

DAHLGREN, ME ;

DAVIES, P ;

DORN, CP ;

FINKE, PE ;

FIRESTONE, RA ;

HAGMANN, WK ;

HALGREN, T ;

KNIGHT, WB ;

MAYCOCK, AL ;

NAVIA, MA ;

OGRADY, L ;

PISANO, JM ;

SHAH, SK ;

THOMPSON, KR ;

WESTON, H ;

ZIMMERMAN, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2513-2521

[6] POLYPEPTIDES .12. PREPARATION OF 2-PYRIDYL ESTERS AND THEIR USE IN PEPTIDE SYNTHESIS [J].

DUTTA, AS ;

MORLEY, JS .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (17) :2896-&

[7] INHIBITION OF HUMAN-LEUKOCYTE ELASTASE .2. INHIBITION BY SUBSTITUTED CEPHALOSPORIN ESTERS AND AMIDES [J].

FINKE, PE ;

ASHE, BM ;

KNIGHT, WB ;

MAYCOCK, AL ;

NAVIA, MA ;

SHAH, SK ;

THOMPSON, KR ;

UNDERWOOD, DJ ;

WESTON, H ;

ZIMMERMAN, M ;

DOHERTY, JB .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2522-2528

[8] A CONVERGENT, ENANTIOSPECIFIC TOTAL SYNTHESIS OF THE NOVEL CYCLODEPSIPEPTIDE (+)-JASPLAKINOLIDE (JASPAMIDE) [J].

GRIECO, PA ;

HON, YS ;

PEREZMEDRANO, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1630-1631

[9]

ITO K, 1981, SYNTHESIS-STUTTGART, P287

[10]

JANOFF A, 1985, AM REV RESPIR DIS, V132, P417

← 1 2 3 →