18804-82-5Relevant academic research and scientific papers
One-Pot synthesis of sulfonamides from primary and secondary amine derived sulfonate salts using cyanuric chloride
Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Asrari, Zeinab,Behrouz, Somayeh,Amini, Zohreh,Behrouz, Marzieh
experimental part, p. 3983 - 3988 (2010/03/26)
A convenient, mild and efficient one-pot synthesis of new sulfonamides is described. The reaction of primary or secondary amine derived sulfonate salts in the presence of cyanuric chloride, triethylamine as base, and anhydrous acetonitrile as solvent at room temperature gives the corresponding sulfonamides in good to excellent yields. Georg Thieme Verlag Stuttgart.
New protocol for converting alcohols into amines
Klepacz,Zwierzak
, p. 1683 - 1689 (2007/10/03)
The reactions between diethyl N-(t-butoxycarbonyl)phosphoramidate 1, diisopropyl azodicarboxylate (DIAD), triphenylphosphine (TPP) and primary or secondary alcohols lead to the corresponding diethyl N-alkyl-N-(t-butoxycarbonyl)phosphoramidates 2a-o. Deprotection of crude 2 by refluxing with p-toluenesulfonic acid monohydrate in ethanol affords ammonium tosylates 3a-o in moderate to good overall yields. The N-alkylation of 1 proceeds stereoselectively with complete inversion of the configuration of the alkyl group.
An optimized version of Gabriel-type nucleophilic amination
Zwierzak, Andrzej
, p. 2287 - 2293 (2007/10/03)
N-Alkylation of primary alkyl bromides with diethyl N-sodio-N-(t- butoxycarbonyl)phosphoramidate 1 carried out in boiling acetonitrile in the presence of 10mol% of tetrabutylammonium bromide as catalyst leads to the corresponding N-alkyl derivatives 2a-I. Deprotection of 2 by refluxing with p-toluenesulfonic acid in ethanol-affords ammonium tosylates 3a-I in reasonable yields.
Two-carbon homologation of Grignard reagents to primary amines
Osowska-Pacewicka, Krystyna,Zwierzak, Andrzej
, p. 333 - 335 (2007/10/03)
A novel, convenient synthesis of N-(diethoxyphosphoryl)aziridine is described. Application of this compound as a synthetic equivalent of an a2 type synthon for aminoethylation of Grignard reagents is demonstrated.
Novel organophosphorus reagents for the synthesis of amines
Zwierzak, Andrzej,Osowska-Pacewicka, Krystyna
, p. 569 - 572 (2007/10/03)
New organophosphorus equivalents of a2 type N-protected amine synthons are presented.
TRIETHYL PHOSPHITE IN ORGANIC SYNTHESIS. A FACILE, ONE-POT CONVERSION OF ALCOHOLS INTO AMINES
Zwierzak, Andrzej
, p. 51 - 54 (2007/10/02)
General protocols for converting primary, secondary, and tertiary alcohols into the corresponding primary amines are presented.
Optimized procedures for one-pot conversion of alkyl bromides into amines via the Staudinger reaction
Koziara,Zwierzak
, p. 1063 - 1065 (2007/10/02)
New optimized procedures for transforming primary and secondary alkyl bromides into the corresponding primary amine salts have been elaborated. Essential modifications of azidation and deprotection of intermediate triethoxyphosphine alkylimides resulted in substantial improvement of the overall yields. Conversion of ammonium tosylates and hydrochlorides into free amines in a nonaqueous medium is described.
THE REACTION OF ETHYL-FORMIMIDATE WITH GRIGNARD REAGENTS: A NEW APPROACH TO ELECTROPHILIC AMINATION
Zawadzki, Stefan
, p. 263 - 268 (2007/10/02)
Addition of Grignard reagents to ethyl-N-(diethoxyphosphoryl)formimidate, 3 followed by aqueous workup and treatment of the resultant diethyl phosphoramidates with p-toluenesulfonic acid in ethanol gives, depending upon the organomagnesium reagent used, the corresponding tosylates of primary or secondary amines in moderate to good yields.The diethoxyphosphoryl moiety remains unchanged upon treatment of 3 with Grignard reagents.Key words: Diethyl-(N-alkylphosphoramidates); Grignard reagents; ammonium tosylates; substitution-addition; substitution-reduction; electrophilic amination.
