A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles

被引：24

作者：

Theodorou, Vassiliki ^{[1
]}

Paraskevopoulos, Georgios ^{[2
]}

Skobridis, Konstantinos ^{[1
]}

机构：

[1] Univ Ioannina, Dept Chem, GR-45110 Ioannina, Greece

[2] Charles Univ Prague, Dept Inorgan & Organ Chem, Hradec Kralove 50005, Czech Republic

来源：

ARKIVOC | 2015年

关键词：

Alkaline hydrolysis; amides; N-substituted amides; nitriles; imidates; anhydrous conditions; protection; CARBOXYLIC-ACIDS; OXYGEN EXCHANGE; ACETALDOXIME; DERIVATIVES; HYDRATION;

D O I：

10.3998/ark.5550190.p009.205

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild protocol for the alkaline hydrolysis of secondary and tertiary amides in non-aqueous conditions, by the use of NaOH in methanol/dichloromethane or methanol/dioxane (1:9) at room temperature or under reflux, has been developed and a plausible reaction mechanism is discussed. Primary amides are hydrolyzed much slower than with the classical procedure, while nitriles are converted selectively to primary amides.

引用

页码：101 / 112

页数：12

共 29 条

[1] AMIDINATION OF LIPASE WITH HYDROPHOBIC IMIDOESTERS [J].

BASRI, M ;

AMPON, K ;

YUNUS, WMZ ;

RAZAK, CNA ;

SALLEH, AB .

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1992, 69 (06) :579-583

[2] MECHANISMS OF CATALYSIS OF NUCLEOPHILIC REACTIONS OF CARBOXYLIC ACID DERIVATIVES [J].

BENDER, ML .

CHEMICAL REVIEWS, 1960, 60 (01) :53-113

[3] CONCURRENT ALKALINE HYDROLYSIS AND ISOTOPIC OXYGEN EXCHANGE OF A SERIES OF P-SUBSTITUTED ACETANILIDES [J].

BENDER, ML ;

THOMAS, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (20) :4183-&

[4]

Bew S.P., 2005, Comprehensive Organic Functional Group Transformations, P19, DOI DOI 10.1016/B0-08-044655-8/00092-1

[5] RECENT PERSPECTIVES CONCERNING THE MECHANISM OF H3O+-PROMOTED AND OH--PROMOTED AMIDE HYDROLYSIS [J].

BROWN, RS ;

BENNET, AJ ;

SLEBOCKATILK, H .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) :481-488

[6] ALKALINE HYDROLYSIS OF BENZAMIDE AND N-METHYL- AND N,N-DIMETHYLBENZAMIDE [J].

BUNTON, CA ;

NAYAK, B ;

OCONNER, C .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (02) :572-&

[7] A mild and convenient 'dry' hydrolysis of amides to carboxylic acids [J].

Chemat, F .

TETRAHEDRON LETTERS, 2000, 41 (20) :3855-3857

[8] TOTAL SYNTHESIS OF BIOTIN BASED ON DERIVATIVES OF 2,5-DIHYDROTHIOPHENE [J].

CONFALONE, PN ;

PIZZOLATO, G ;

USKOKOVIC, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (09) :1630-1633

[9] HYDROLYSIS AND CARBONYL-OXYGEN EXCHANGE IN TERTIARY AMIDES - ESTIMATION OF THE FREE-ENERGY CHANGES FOR BREAKDOWN AND CONFORMATIONAL-CHANGES OF TETRAHEDRAL INTERMEDIATES [J].

DESLONGCHAMPS, P ;

BARLET, R ;

TAILLEFER, RJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (20) :2167-2172

[10] Computational study of the reactivity of N-phenylacetamides in the alkaline hydrolysis reaction [J].

Galabov, B ;

Cheshmedzhieva, D ;

Ilieva, S ;

Hadjieva, B .

JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (51) :11457-11462

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