SIMPLE AND CONDENSED BETA-LACTAMS .14. ANOMALOUS BEHAVIOR OF 1-(4-METHOXYPHENYL)-4-(TETRAZOL-5-YLMETHYL)AZETIDIN-2-ONE TOWARDS CERIUM(IV) AMMONIUM-NITRATE

被引：20

作者：

FETTER, J ^{[1
]}

KESKENY, E ^{[1
]}

CZUPPON, T ^{[1
]}

LEMPERT, K ^{[1
]}

KAJTARPEREDY, M ^{[1
]}

TAMAS, J ^{[1
]}

机构：

[1] HUNGARIAN ACAD SCI,CENT RES INST CHEM,H-1525 BUDAPEST,HUNGARY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 22期

关键词：

D O I：

10.1039/p19920003061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 1-(4-methoxyphenyl)azetidin-2-one 7 with cerium(IV) ammonium nitrate (CAN) fails to yield the N-deprotected product 6. Depending on the mode of work-up, N-substituted products 8-13 are obtained instead. The formation of these products may be rationalized by assuming interaction of the nucleophilic tetrazole and electrophilic quinone imine moieties of intermediate 21 to afford, after deprotonation, the spirocyclic quinone aminal 25. The latter, in contrast to quinone imine derivatives of type 3, is stable to hydrolysis under the conditions applied but reacts readily both with added sodium chloride and bromide as well as with reducing agents (NaHSO3, I-).

引用

页码：3061 / 3067

页数：7

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