AN EFFICIENT METHOD FOR HYDROLYSIS OF N-MONOSUBSTITUTED AMIDES UTILIZATION OF INTRAMOLECULAR N-O ACYL MIGRATION IN HYDROXYPIVALIMIDES

被引：14

作者：

TSUNODA, T ^{[1
]}

SASAKI, O ^{[1
]}

TAKEUCHI, O ^{[1
]}

ITO, S ^{[1
]}

机构：

[1] TOKUSHIMA BUNRI UNIV,FAC PHARMACEUT SCI,TOKUSHIMA 770,JAPAN

来源：

TETRAHEDRON | 1991年 / 47卷 / 24期

关键词：

HYDROLYSIS; N-MONOSUBSTITUTED CARBOXAMIDES; N-O ACYL MIGRATION;

D O I：

10.1016/S0040-4020(01)86433-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and versatile method for the hydrolysis of N-monosubstituted carboxamides has been developed. The method consists of two steps: the conversion to acetoxypivalimides (greater-than-or-equal-to 90% yield) and their mild alkaline hydrolysis (70 approximately 90% yield). No epimerization at the alpha-position of the acyl group took place in the process. The amine part of the original amides can be recovered in good yield.

引用

页码：3925 / 3934

页数：10

共 32 条

[31] Design and synthesis of a novel water-soluble Aβ1-42 isopeptide:: an efficient strategy for the preparation of Alzheimer's disease-related peptide, Aβ1-42, via O-N intramolecular acyl migration reaction
Sohma, Y
Sasaki, M
Hayashi, Y
Kimura, T
Kiso, Y
TETRAHEDRON LETTERS, 2004, 45 (31) : 5965 - 5968
[32] Efficient and practical method for synthesizing N-heterocyclic compounds using intramolecular nucleophilic acyl substitution reactions mediated by Ti(O-i-Pr)(4)/2i-PrMgX reagent. Synthesis of quinolones, pyrroles, indoles, and optically active N-heterocycles including allopumiliotoxin alkaloid 267A
Okamoto, S
Iwakubo, M
Kobayashi, K
Sato, F
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (30) : 6984 - 6990

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