Acyl vs sulfonyl transfer in N-acyl β-sultams and 3-oxo-β-sultams

被引：17

作者：

Ahmed, N ^{[1
]}

Tsang, WY ^{[1
]}

Page, MI ^{[1
]}

机构：

[1] Univ Huddersfield, Dept Chem & Biol Sci, Huddersfield HD1 3DH, W Yorkshire, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 02期

关键词：

D O I：

10.1021/ol0361305

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] N-Acylsulfonamides usually react with nucleophiles by acyl transfer and C-N bond fission. However, the hydrolysis of N-acyl beta-sultams is a sulfonyl transfer reaction that occurs with S-N fission and opening of the four-membered ring. Similar to other beta-sultams, the N-acyl derivatives are at least 10(6)-fold more reactive than N-acyl sulfonamides. 3-Oxo-beta-sultams are both beta-lactams and beta-sultams but also hydrolyze with preferential S-N bond fission.

引用

页码：201 / 203

页数：3

共 27 条

[1] Reactivity and mechanism in the hydrolysis of β-sultams [J].

Baxter, NJ ;

Rigoreau, LJM ;

Laws, AP ;

Page, MI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) :3375-3385

[2] The hydrolytic reactivity of beta-sultams [J].

Baxter, NJ ;

Laws, AP ;

Rigoreau, L ;

Page, MI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (11) :2245-2246

[3] THE HYDROLYSES OF BENZAMIDES, METHYLBENZIMIDATIUM IONS, AND LACTAMS IN AQUEOUS SULFURIC-ACID - THE EXCESS ACIDITY METHOD IN THE DETERMINATION OF REACTION-MECHANISMS [J].

COX, RA ;

YATES, K .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (19) :2853-2863

[4]

ERIKSSON SO, 1973, ACTA PHARM SUEC, V10, P63

[5] SULFONYL TRANSFER-REACTIONS [J].

GORDON, IM ;

MASKILL, H ;

RUASSE, MF .

CHEMICAL SOCIETY REVIEWS, 1989, 18 (02) :123-151

[6] EFFICIENT INHIBITION OF HUMAN-LEUKOCYTE ELASTASE AND CATHEPSIN-G BY SACCHARIN DERIVATIVES [J].

GROUTAS, WC ;

HOUSERARCHIELD, N ;

CHONG, LS ;

VENKATARAMAN, R ;

EPP, JB ;

HUANG, H ;

MCCLENAHAN, JJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (21) :3178-3181

[7] A BENZISOTHIAZOLONE CLASS OF POTENT, SELECTIVE MECHANISM-BASED INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE [J].

HLASTA, DJ ;

BELL, MR ;

BOAZ, NW ;

COURT, JJ ;

DESAI, RC ;

FRANKE, CA ;

MURA, AJ ;

SUBRAMANYAM, C ;

DUNLAP, RP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (15) :1801-1806

[8]

KICE JL, 1980, ADV PHYS ORG CHEM, V17, P65

[9]

KICE JL, 1972, PROG INORG CHEM, V17, P147

[10] PH OPTIMIZATION OF NUCLEOPHILIC REACTIONS IN WATER [J].

KING, JF ;

RATHORE, R ;

LAM, JYL ;

GUO, ZR ;

KLASSEN, DF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3028-3033

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