5496-07-1Relevant academic research and scientific papers
A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles
Bhatt, Ashish,Kant, Ravi,Kumar, Sonu,Reddy, Yella,Sarmah, Manash P.
, (2021/11/23)
Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation of N-hydroxy intermediate, which at higher temperature cleaves to afford the desired product. This approach achieved reductions in reaction times, higher yields, cleaner reactions than the previously described synthetic processes.
PROTON ACCEPTOR IMINIUM/CARBOCATION-TYPE COUPLING AGENTS
-
, (2010/06/19)
Novel iminium-type coupling agents containing proton acceptors in their iminium moiety, which can be used beneficially as coupling agents in various chemical polypeptide and/or polynucleotide syntheses, and are particularly useful as yield enhancing and racemization suppressing coupling agents for use in peptide syntheses, are disclosed. Further disclosed are a process of preparing such iminium-type coupling agents and their use in the preparation of polypeptides and/or polynucleotides.
Synthesis and application of N-hydroxylamine derivatives as potential replacements for HOBt
El-Faham, Ayman,Albericio, Fernando
supporting information; experimental part, p. 1499 - 1501 (2009/07/11)
Several heterocycles containing N-hydroxylamine were prepared and tested as coupling additives to replace the use of N-hydroxybenzolriazole (HOBt.) derivatives. On the basis of our results on coupling yield and racemization-suppressing properties, we propose N-hydroxyindolin-2-one and 6- cfiloro-N-hydroxy-2-phenylbenzimidazole as suitable substitutes for HOBt. Wiley-VCH Verlag GmbH & Co. KGaA.
N-[(diphenoxyphosphoryl)oxy]-2-phenyl-1H-benzimidazole as a versatile reagent for synthesis O-alkylhydroxamic acids
Kokare, Nagnnath D.,Shinde, Devanand B.
, p. 981 - 986 (2008/09/21)
(Chemical Equation Presented) Highly efficient reagent, N-[(diphenoxyphosphoryl)oxy]-2-phenyl-1H-benzimidazole was synthesized and its applicability was demonstrated for the synthesis of O-alkyl hydroxamic acids. The efficiency of the reagent was evaluate
Design, synthesis and utilization of a novel coupling reagent for the preparation of O-alkyl hydroxamic acids
Kokare, Nagnnath D.,Nagawade, Rahul R.,Rane, Vipul P.,Shinde, Devanand B.
, p. 4437 - 4440 (2008/02/03)
An efficient novel reagent, phosphoric acid diethyl ester 2-phenyl-benzimidazol-1-yl ester, was designed, and synthesized and its applicability was demonstrated for the preparation of O-alkyl hydroxamic acids. The O-alkyl hydroxamic acids of N-protected a
Organophosphorus esters of 1-hydroxy-2-phenylbenzimidazole: Synthesis and utilization as novel peptide coupling reagents
Kokare, Nagnnath D.,Nagawade, Rahul R.,Rane, Vipul P.,Shinde, Devanand B.
, p. 766 - 772 (2008/01/04)
Highly efficient coupling reagents - phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester, diphenylphosphinic acid 2-phenylbenzimidazol-1- yl ester and phosphoric acid diphenyl ester 2-phenylbenzimidazol-1-yl ester - were designed, synthesized and successfully applied in peptide coupling reactions. Their efficiency was evaluated through the synthesis of a range of amides and peptides, and the extent of racemization was studied by HPLC and found to be negligible. The mechanism of action is probably similar to those found for organophoshorus esters of hydroxybenzotriazole: a presumption supported by the isolation and characterization by mass spectrometry and 1H NMR of some of the proposed intermediates. Georg Thieme Verlag Stuttgart.
Novel anti-infection agents: Small-molecule inhibitors of bacterial transcription factors
Bowser, Todd E.,Bartlett, Victoria J.,Grier, Mark C.,Verma, Atul K.,Warchol, Taduesz,Levy, Stuart B.,Alekshun, Michael N.
, p. 5652 - 5655 (2008/02/13)
Structure-based drug design was utilized to identify potent small-molecule inhibitors of proteins within the AraC family of bacterial transcription factors, which control virulence in medically important microbes. These agents represent a novel approach to fight infectious disease and may be less likely to promote resistance development. These compounds lack intrinsic antibacterial activity in vitro and were able to limit a bacterial infection in a mouse model of urinary tract infection.
Synthesis of N-alkoxybenzimidazoles and N-alkoxypyrimidazoles
Gardiner, John M,Goss, Andrew D,Majid, Tahir,Morley, Andrew D,Pritchard, Robin G,Warren, John E
, p. 7707 - 7710 (2007/10/03)
A variety of novel N-alkoxy aromatic-fused imidazoles have been prepared in a simple two-step process from 2-fluoro nitroaromatics and 2-chloro-3-nitropyridine. The imidazole forming step involves tandem heterocyclisation and O-alkylation with an in situ alkylating agent, and supports prior mechanistic proposals. Additional mechanistic experiments are described. The protocol is versatile with respect to both substrate halo-nitro aromatics and to the nature of the added electrophile (halides) used in the second step, and thereby significantly extends the scope of this reaction and its applicability to diverse synthesis. This methodology can also be used to generate various types of novel N-alkoxypyrimidazoles (4-deazapurine analogues), and an X-ray structure of one such pyrimidazole is presented.
