6263-08-7Relevant articles and documents
Synthesis of primary amines and N-methylamines by the electrophilic amination of Grignard reagents with 2-imidazolidinone O-sulfonyloxime
Kitamura, Mitsuru,Chiba, Shunsuke,Narasaka, Koichi
, p. 1063 - 1070 (2007/10/03)
2-Imidazolidinone O-sulfonyloxime reacts with various aryl and alkyl Grignard reagents as an electrophilic amination reagent, giving N-alkylated imines. The resulting imines are transformed to primary amines and N-methyl secondary amines by hydrolysis with CsOH and LiAlH4 reduction, respectively.
Process for the production of N,O-disubstituted urethanes and use thereof as starting materials for the production of organic isocyanates
-
, (2008/06/13)
The present invention is directed to a process for the production of N,O-disubstituted urethanes comprising reacting N-mono- or N,N'-disubstituted ureas or linear polyureas with aliphatic carbonic esters.
Orthoamides, XXXVIII. - Contributions to the Chemistry of Orthocarbonic Acid Esters and α,α,α-Trialkoxyacetonitriles
Kantlehner, Willi,Maier, Thomas,Loeffler, Wolfgang,Kapassakalidis, Joanis J.
, p. 507 - 529 (2007/10/02)
The reactivity of the orthocarbonates 4 and the nitriles 1 has been investigated.Carboxylic acids are esterified by 4b. Orthocarbonates 4c-f and 9b are prepared by transesterification of 4b.Mixed substituted orthocarbonates 8c-f are obtained from the nitriles 1a,b.The nitriles 2a and 3a react with alkali alcoholate in alcohol to yield the orthocarbamic acid esters 13a,b. Spirocyclic orthocarbonates 17a-d are prepared from 4b and 1,2 or 1,3-dioles, respectively. The reaction of phenol with 1b affords the mixed substituted orthocarbonate 18a. Catechol is converted by 1a into the orthocarbonate 20a.Reactions of 4b with amines and ami ne derivatives are studied. In the course of these investigations guanidines 21, imidocarbonic acid esters 22a-c, 30, carbamic acid esters 25, ureas 26, the isourea derivative 29, as well as the 1,3,4-oxadiazole 31 are prepared. The mechanism of these reactions is discussed. Imidocarbonic acid esters 22d-f, 38, N-cyanocarbamates 39, and isoureas 37 can be prepared from 1b and amines or amine derivatives. 2a as well as 13b react with cyanamide to give the N-cyanoisourea 40. Ureas 26 are formed in the reaction of 1a,b with secondary amines at elevated temperatures.The guanidinium cyanide 41a can be obtained by reaction of pyrrolidine with 1b in ether, whereas under similiar conditions from 1a and pyrrolidine the amidine 42 is produced. o-Aminophenol, o-phenylenediamine and anthranilic acid are cyclized by 4b or 1b to afford the heterocyclic compounds 43-45. α- and β-amino acids are transformed by 4b or 1b into the N-(ethoxycarbonyl)amino acid esters 46 and 47, respectively.