21737-87-1Relevant academic research and scientific papers
A QSAR for the mutagenic potencies of twelve 2-amino- trimethylimidazopyridine isomers: Structural, quantum chemical, and hydropathic factors
Knize, Mark G.,Hatch,Tanga,Lau,Colvin
, p. 132 - 146 (2006)
An isomeric series of heterocyclic amines related to one found in heated muscle meats was investigated for properties that predict their measured mutagenic potency. Eleven of the 12 possible 2-amino-trimethylimidazopyridine (TMIP) isomers were tested for
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 (2002)
[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
Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis
K?ring, Laura,Sitte, Nikolai A.,Bursch, Markus,Grimme, Stefan,Paradies, Jan
supporting information, p. 14179 - 14183 (2021/09/03)
The metal-free catalytic hydrogenation of secondary carboxylic acid amides is developed. The reduction is realized by two new catalytic reactions. First, the amide is converted into the imidoyl chloride by triphosgene (CO(OCCl3)2) using novel phosphorus(V) catalysts. Second, the in situ generated imidoyl chlorides are hydrogenated in high yields by an FLP-catalyst. Mechanistic and quantum mechanical calculations support an autoinduced catalytic cycle for the hydrogenation with chloride acting as unusual Lewis base for FLP-mediated H2-activation.
Frustrated Lewis Pair Catalyzed Hydrogenation of Amides: Halides as Active Lewis Base in the Metal-Free Hydrogen Activation
Sitte, Nikolai A.,Bursch, Markus,Grimme, Stefan,Paradies, Jan
supporting information, p. 159 - 162 (2019/01/04)
A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,6-F2-C6H3)3 in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and α-branched carboxamides.
Transition metal-free one-pot synthesis of 2-substituted 3-carboxy-4-quinolone and chromone derivatives
Lin, Jian-Ping,Long, Ya-Qiu
, p. 5313 - 5315 (2013/06/27)
A novel one-pot synthesis of the 2-substituted 3-carboxy-4-quinolone/ chromone derivatives from readily available 3-oxo-3-arylpropanoates and amides/acyl chlorides is reported, without any transition metal aid. The Royal Society of Chemistry 2013.
Preparation of 14C-labeled 1,2,4-triazoles from [ 14C]-labeled tetrazoles via Diels-Alder reaction: Synthesis of 11β-hydroxysteroid dehydrogenenase type 1 (HSD1) inhibitors
Ho, Jonathan Z.,Braun, Matthew P.
scheme or table, p. 431 - 433 (2011/04/24)
[14C]-labeled HSD1 inhibitors were synthesized for metabolic profiling and selection of drug candidates. A three-step reaction sequence was applied. 1-Iodo-2-trifluoromethylbenzene was labeled via a Pd-catalyzed cyanation with Zn(14CN)2 to give [cyano- 14C]2-trifluorobenzonitrile (3). The nitrile was then converted to 14C-labeled tetrazole (4). Diels-Alder reaction of 4 with the appropriate imidate yielded the desired 14C-labeled triazole tracers exemplified by 7c. (Chemical Equation Presented). Copyright
Synthesis of two potential heterocyclic amine food mutagens
Tanga, Mary J.,Kozocas, Joseph A.,Tochimoto, Todd K.
, p. 661 - 665 (2008/09/21)
(Chemical Equation Presented) The syntheses of two potential food mutagens formed during cooking, 2-amino-3,6,7-trimethyl-3H-imidazo[4,5-b]pyridine (1) and 2-amino-3,6,7-trimethyl-3H-imidazo[4,5-c]pyridine (2), are described.
N,N′-Dimethylbenzamidine and derivatives: Preparations, structures, and hydrogen bond networks therein
Chen, Wei-Zhong,Xu, Guo-Lin,Jablonski, Conrad G.,Ren, Tong
experimental part, p. 90 - 94 (2009/02/07)
Reported herein are the syntheses of N,N′-dimethylbenzamidine (HDMBA, 1) and its phenyl substituted derivatives HYDMBA with phenyl substituents Y as 3-CH3O (2), and 3-CF3 (3), and the determination of single crystal structures of com
Preparation of 1,5-disubstituted tetrazoles under phase-transfer conditions
Artamonova,Zhivich,Dubinskii,Koldobskii
, p. 1428 - 1430 (2007/10/03)
Imidoyl chlorides, obtained by common methods from a wide range of aromatic mono- and diamides, are smoothly converted to the corresponding tetrazoles in high yields by treatment with NaN3 under phase-transfer conditions.
TETRAZOLES. XXIX. IMIDOYLATION OF 5-ARYLTETRAZOLES UNDER PHASE-TRANSFER CATALYSIS CONDITIONS. FORMATION OF 3H-1,3,4-BENZOTRIAZEPINES
Koldobskii, G. I.,Nikonova, I. V.,Zhivich, A. B.,Ostrovskii, V. A.,Poplavskii, V. S.
, p. 160 - 163 (2007/10/02)
Reaction of 5-aryltetrazoles with N-arylbenzimidoyl chlorides in a methylene chloride-water two-phase system in the presence of tetrabutylammonium bromide or 2,3-diphenyl-5-butyltetrazolium bromide results in the formation of isomeric 1-imidoyl- and 2-imidoyl-5-aryltetrazoles, which are converted to 3H-1,3,4-benzotriazepines upon heating in toluene, m-xylene, or dioxane.
