A Synthesis of Acetamidines

被引：65

作者：

Harjani, Jitendra R. ^{[1
]}

Liang, Chen ^{[1
]}

Jessop, Philip G. ^{[1
]}

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 06期

基金：

加拿大自然科学与工程研究理事会;

关键词：

CARBON-DIOXIDE; IONIC LIQUIDS; AMIDINES; CHEMISTRY;

D O I：

10.1021/jo102358d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The condensation of primary amine with N,N-dimethylacetamide dimethyl acetal yields a mixture of acetamidine and imidate ester. The product distribution in this reaction depends on the temperature, solvent, and structure of the primary amine. It is possible to suppress the formation of imidate ester by performing the reaction in the presence of excess dimethyl amine, yielding acetamidine as the exclusive product. For acetamidines that cannot be purified either by crystallization or distillation, this new method is necessary for the generation of pure acetamidines in good yields.

引用

页码：1683 / 1691

页数：9

共 21 条

[1] Preparation and Utility of Trihaloethyl Imidates: Useful Reagents for the Synthesis of Amidines [J].

Caron, Stephane ;

Wei, Lulin ;

Douville, Jasmin ;

Ghosh, Arun .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :945-947

[2] Carbon Dioxide Induced Phase Switching for Homogeneous-Catalyst Recycling [J].

Desset, Simon. L. ;

Cole-Hamilton, David J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) :1472-1474

[3]

Dunn P.J., 2005, Compreh. Org. Funct. Group Transform. II, V5, P655

[4] Advances in the coordination chemistry of amidinate and guanidinate ligands [J].

Edelmann, Frank T. .

ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 57, 2008, 57 :183-352

[5] Lanthanide amidinates and guanidinates: from laboratory curiosities to efficient homogeneous catalysts and precursors for rare-earth oxide thin films [J].

Edelmann, Frank T. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2253-2268

[6]

Forkner MW., 2004, Kirk-Othmer Encyclopedia of Chemical Technology, V12, P644

[7]

Gabriel S., 1887, Chem. Ber, V20, P2224, DOI DOI 10.1002/CBER.18870200227

[8]

Greenhill J V, 1993, Prog Med Chem, V30, P203, DOI 10.1016/S0079-6468(08)70378-3

[9] Antagonists of the P2X7 Receptor. From Lead Identification to Drug Development [J].

Guile, Simon D. ;

Alcaraz, Lilian ;

Birkinshaw, Timothy N. ;

Bowers, Keith C. ;

Ebden, Mark R. ;

Furber, Mark ;

Stocks, Michael J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (10) :3123-3141

[10] Benign coupling of reactions and separations with reversible ionic liquids [J].

Hart, Ryan ;

Pollet, Pamela ;

Hahne, Dominique J. ;

John, Ejae ;

Llopis-Mestre, Veronica ;

Blasucci, Vittoria ;

Huttenhower, Hillary ;

Leitner, Walter ;

Eckert, Charles A. ;

Liotta, Charles L. .

TETRAHEDRON, 2010, 66 (05) :1082-1090

← 1 2 3 →