65052-85-9Relevant academic research and scientific papers
Synthesis of various acylating agents directly from carboxylic acids
Pilathottathil, Fathima,Vineet Kumar, Doppalapudi,Kaliyamoorthy, Alagiri
supporting information, p. 1622 - 1632 (2020/04/27)
A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.
Acid-induced conformational alteration of cis-preferential aromatic amides bearing N-methyl-N-(2-pyridyl) moiety
Okamoto, Iwao,Terashima, Masayuki,Masu, Hyuma,Nabeta, Mayumi,Ono, Kaori,Morita, Nobuyoshi,Katagiri, Kosuke,Azumaya, Isao,Tamura, Osamu
experimental part, p. 8536 - 8543 (2011/11/28)
A series of cis-preferential aromatic N-methyl amides was designed and synthesized, and acid-induced conformational alteration of these compounds was investigated by means of NMR measurements in solution and X-ray crystal structure analysis. Compounds with a terminal N-methyl-N-(2-pyridyl) amide unit showed acid-induced conformational change from cis to trans, while those with a terminal N-methyl-2-pyridinecarboxamide unit showed a change of the carbonyl orientation from anti to syn with retention of cis conformation.
Microwave-assisted synthesis of weinreb and MAP aryl amides via pd-catalyzed heck aminocarbonylation using Mo(CO)6 or W(CO) 6
Wieckowska, Anna,Fransson, Rebecca,Odell, Luke R.,Larhed, Mats
supporting information; experimental part, p. 978 - 981 (2011/03/22)
A simple and expedient process for the Heck aminocarbonylative synthesis of Weinreb and MAP amide acylating agents, from aryl halides, is reported. This methodology utilizes solid sources of CO making it readily accessible to chemists working in small-scale laboratory applications.
Direct dehydrative n-pyridinylation of amides
Medley, Jonathan William,Movassaghi, Mohammad
supporting information; experimental part, p. 1341 - 1344 (2009/07/04)
Electrophilic activation of secondary amides with trifluo-romethanesulfonic anhydride in the presence of 2-fluoropy-ridine followed by introduction of a pyridine N-oxide derivative and warming affords the corresponding N-pyridi-nyl tertiary amide derivati
A mild method for the formation and in situ reaction of imidoyl chlorides: conversion of pyridine-1-oxides to 2-aminopyridine amides.
Manley, Peter J,Bilodeau, Mark T
, p. 3127 - 3129 (2007/10/03)
[reaction: see text] A mild, practical, one-pot method for the generation of imidoyl chlorides and their subsequent in situ reaction with pyridine-1-oxides is described. The imidoyl chlorides were formed from the reaction of secondary amides with a stoich
