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

被引：23

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
BASRI, M
AMPON, K
YUNUS, WMZ
RAZAK, CNA
SALLEH, AB
[J]. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1992, 69 (06) : 579 - 583
[2] MECHANISMS OF CATALYSIS OF NUCLEOPHILIC REACTIONS OF CARBOXYLIC ACID DERIVATIVES
BENDER, ML
[J]. CHEMICAL REVIEWS, 1960, 60 (01) : 53 - 113
[3] CONCURRENT ALKALINE HYDROLYSIS AND ISOTOPIC OXYGEN EXCHANGE OF A SERIES OF P-SUBSTITUTED ACETANILIDES
BENDER, ML
THOMAS, RJ
[J]. 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
BROWN, RS
BENNET, AJ
SLEBOCKATILK, H
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) : 481 - 488
[6] ALKALINE HYDROLYSIS OF BENZAMIDE AND N-METHYL- AND N,N-DIMETHYLBENZAMIDE
BUNTON, CA
NAYAK, B
OCONNER, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (02) : 572 - &
[7] A mild and convenient 'dry' hydrolysis of amides to carboxylic acids
Chemat, F
[J]. TETRAHEDRON LETTERS, 2000, 41 (20) : 3855 - 3857
[8] TOTAL SYNTHESIS OF BIOTIN BASED ON DERIVATIVES OF 2,5-DIHYDROTHIOPHENE
CONFALONE, PN
PIZZOLATO, G
USKOKOVIC, MR
[J]. 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
DESLONGCHAMPS, P
BARLET, R
TAILLEFER, RJ
[J]. 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
Galabov, B
Cheshmedzhieva, D
Ilieva, S
Hadjieva, B
[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (51) : 11457 - 11462

← 1 2 3 →