Novel and facile transformation of N,N-Disubstituted glycylamides into corresponding cyanamides by using pentavalent iodine reagents in combination with tetraethylammonium bromide

被引：45

作者：

Chaudhari, Kiran H. ^{[1
]}

Mahajan, Ulhas S. ^{[1
]}

Bhalerao, Dinesh S. ^{[1
]}

Akamanchi, Krishnacharya G. ^{[1
]}

机构：

[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Bombay 400019, Maharashtra, India

来源：

SYNLETT | 2007年 / 18期

关键词：

pentavalent iodine reagents; o-iodoxybenzoic acid; Dess-Martin periodinane; tetraethylammonium bromide; glycylamides; cyanamides;

D O I：

10.1055/s-2007-991093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel and facile transformation of N,N-disubstituted glycylamides into corresponding cyanamides using pentavalent iodine reagents and tetraethylammonium bromide is discussed. The advantages of this system are use of non toxic reagents, shorter reaction times and moderate to good yields.

引用

页码：2815 / 2818

页数：4

共 33 条

[1]

BAKER JA, 1971, Patent No. 2106167

[2]

Bakunov SA, 2000, SYNTHESIS-STUTTGART, P1148

[3] o-Iodoxybenzoic acid- and tetraethylammonium bromide-mediated oxidative transformation of primary carboxamides to one-carbon dehomologated nitriles [J].

Bhalerao, Dinesh S. ;

Mahajan, Ulhas S. ;

Chaudhari, Kiran H. ;

Akamanchi, Krishnacharya G. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02) :662-665

[4]

BOLTZE KH, 1967, LIEBIGS ANN CHEM, V709, P63

[5]

Chaudhari SS, 1999, SYNTHESIS-STUTTGART, P760

[6]

GILMAN AG, 1990, GOODMAN GILMANS PHAR, P899

[7] SUBSTITUTED ALPHA-(4-MORPHOLINYL)-ACETONITRILES AND RELATED COMPOUNDS [J].

HENRY, RA ;

DEHN, WM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (06) :2804-2806

[8] N-CYANOAZIRIDINES AND 1-ALKYLALKYLIDENECYANAMIDES FROM CYANOGEN AZIDE AND OLEFINS [J].

HERMES, ME ;

MARSH, FD .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (19) :2969-&

[9] PSEUDO-HALIDE COMPLEXES OF TRANSITION METALS .1. SYNTHESIS AND PROPERTIES OF COBALT(II), NICKEL(II), COPPER(II), AND ZINC(II) DERIVATIVES [J].

HOLLEBONE, BR ;

NYHOLM, RS .

JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1971, (02) :332-+

[10] Synthesis and pharmacological evaluation of N-(2,5-disubstituted phenyl)-N′-(3-substituted phenyl)-N′-methylguanidines as N-methyl-D-aspartate receptor ion-channel blockers [J].

Hu, LY ;

Guo, JQ ;

Magar, SS ;

Fischer, JB ;

Burke-Howie, KJ ;

Durant, GJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (26) :4281-4289

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