Conversion of aldehydes to amides via dimethyl sulfoxide oxidation of the corresponding α-aminonitriles

被引：17

作者：

Enders, D ^{[1
]}

Amaya, AS ^{[1
]}

Pierre, F ^{[1
]}

机构：

[1] Rhein Westfal TH Klinikum, Inst Organ Chem, D-52074 Aachen, Germany

来源：

NEW JOURNAL OF CHEMISTRY | 1999年 / 23卷 / 03期

关键词：

D O I：

10.1039/a809770d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Unsaturated, aryl and heteroaryl N-dialkyl-alpha-aminonitriles are easily oxidized at room temperature to their corresponding tertiary N-dialkylamides by using dimethyl sulfoxide and bases like (BuOK)-O-t or KOH, The reaction offers an efficient two-step conversion of aldehydes to N-dialkyamides.

引用

页码：261 / 262

页数：2

共 17 条

[1]

AHLBRECHT H, 1975, SYNTHESIS-STUTTGART, P512

[2] ELECTROPHILIC AMINATION OF ACYL ANION EQUIVALENTS - MILD OXIDATION OF ALDEHYDES TO AMIDES VIA O-(TRIMETHYLSILYL)ALDEHYDE CYANOHYDRIN ANIONS [J].

BOCHE, G ;

BOSOLD, F ;

NIESSNER, M .

TETRAHEDRON LETTERS, 1982, 23 (32) :3255-3256

[3]

BRUNO A, 1966, GAZZ CHIM ITAL, V96, P986

[4]

CHUANG TH, 1990, SYNLETT, P733

[5] NEW AND HIGHLY EFFECTIVE METHOD FOR OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS TO CARBONYL-COMPOUNDS [J].

COREY, EJ ;

KIM, CU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (21) :7586-&

[6]

DADACOSTA R, 1979, J AM CHEM SOC, V101, P4381

[7] ALPHA-AMINONITRILES .1. SIMPLE SYNTHESIS OF DEOXYBENZOINS [J].

DYKE, SF ;

TILEY, EP ;

WHITE, AWC ;

GALE, DP .

TETRAHEDRON, 1975, 31 (09) :1219-1222

[8]

KOPECKY J, 1966, CHEM IND-LONDON, P1529

[9] A NEW AND SELECTIVE METHOD OF OXIDATION [J].

KORNBLUM, N ;

POWERS, JW ;

ANDERSON, GJ ;

JONES, WJ ;

LARSON, HO ;

LEVAND, O ;

WEAVER, WM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (24) :6562-6562

[10]

MANCUSO AJ, 1981, SYNTHESIS-STUTTGART, P165

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