4203-31-0Relevant academic research and scientific papers
NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds
Lu, Guan-Han,Huang, Tzu-Chia,Hsueh, Hsiao-Chin,Yang, Shin-Cherng,Cho, Ting-Wei,Chou, Ho-Hsuan
supporting information, p. 4839 - 4842 (2021/05/25)
A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).
Metal-Free Insertion Reactions of Diazo Carbonyls to Azlactones
De Mello, Amanda C.,Momo, Patrícia B.,Burtoloso, Antonio C. B.,Amarante, Giovanni W.
, p. 11399 - 11406 (2018/09/12)
Insertion reactions of diazo carbonyls to azlactones in basic conditions have been performed. The developed method allows the preparation of a wide range of oxazole derivatives in yields ranging from 74 to 98%. Different substituents on both azlactone rings and diazo carbonyls do not compromise the methodology, even those containing stereogenic centers. Isotopic labeling experiments revealed the mechanism may proceed through a rare diazo carbonyl activation by an ammonium salt derivative.
One-pot synthesis of trans-β-lactams from ferrocenylketene generated by thermal Wolff rearrangement
Liu, Mingshun,Wang, Jian’an,Yuan, Xiaoxi,Jiang, Rong,Fu, Nanyan
supporting information, p. 2369 - 2377 (2017/12/12)
A series of β-lactams containing the ferrocene moiety were synthesized through the Staudinger reaction between ferrocenylketene generated by the thermal Wolff rearrangement of the corresponding diazo ketone and various imines. The stereochemical outcome h
Facile access to 2,2-disubstituted indolin-3-ones: Via a cascade Fischer indolization/Claisen rearrangement reaction
Xia, Zilei,Hu, Jiadong,Gao, Yu-Qi,Yao, Qizheng,Xie, Weiqing
supporting information, p. 7485 - 7488 (2017/07/12)
An efficient approach for the synthesis of 2,2-disubstituted indolin-3-ones is described. From readily accessible aryl hydrazines and allyloxyketones, 2,2-disubstituted indolin-3-ones could be obtained in good to excellent yields under mild reaction condi
An efficient PEG-400 mediated catalyst free green synthesis of 2-amino-thiazoles from α-diazoketones and thiourea
Babu, B Hari,Vijay,Murali Krishna, K Bala,Sharmila,Ramana, M Baby
, p. 1475 - 1478 (2016/09/19)
A simple and efficient method has been developed for the synthesis of 2-aminothiazoles from α-diazoketones using PEG-400 solvent system. This novel synthetic approach involves the reaction between thiourea and α-diazoketones in PEG-400 at 100 °C to yield the corresponding 2-aminothiazoles in good yields. The method is simple, rapid and generates thiazole derivatives in excellent yields without the use of any catalysts. This green protocol can be utilized for fast synthesis of various 2-aminothiazoles in good yields. [Figure not available: see fulltext.]
One-pot synthesis of polyfunctional pyrazoles: An easy access to α-diazoketones from arylglyoxal monohydrates and tosylhydrazine
Shu, Wen-Ming,Ma, Jun-Rui,Zheng, Kai-Lu,Sun, Hui-Ying,Wang, Mei,Yang, Yan,Wu, An-Xin
, p. 9321 - 9329 (2015/03/05)
A new and efficient method for the generation of α-diazoketones has been developed from arylglyoxal monohydrates and tosylhydrazine at room temperature. 1,3-Dipolar cycloaddition reactions were used to constructing polyfunctional pyrazole derivatives by the reaction of generated α-diazoketones in situ with electron-deficient alkenes, quinones and coumarins in one pot. The one-dimensional molecular packing of 1H-benzo[f]indazole-4,9-dione derivatives along the c direction demonstrated a helical chain formation via N-H?O hydrogen-bonding.
Amination of phenylketene revisit. Substituent effect on reactivity
Badal, Md. Mizanur Rahman,Zhang, Min,Kobayashi, Shinjiro,Mishima, Masaaki
, p. 856 - 863 (2013/08/15)
The asymmetric stretching frequencies of the ketene group of the m,p-substituted phenylketenes were found to be correlated with σ The substituent effects for the second-order rate constants of phenylketenes with various amines were not correlated linearly
A cascade approach to pyridines from 2-Azido-2,4-dienoates and α-diazocarbonyl compounds
Chen, Zheng-Bo,Hong, Deng,Wang, Yan-Guang
supporting information; experimental part, p. 903 - 905 (2009/06/20)
A one-pot synthesis of substituted pyridines via a cascade reaction of 2-azido-2,4-dienoates with α-diazocarbonyl compounds and triphenylphosphine is reported. The process involves a Staudinger-Meyer reaction, a Wolff rearrangement, an aza-Wittig reaction, and an electrocyclic ring- closure. The procedure is general and efficient. The substrates are readily available.
First example of the coupling of α-diazoketones with thiourea: a novel route for the synthesis of 2-aminothiazoles
Yadav,Reddy, B.V. Subba,Rao, Y. Gopala,Narsaiah
, p. 2381 - 2383 (2008/09/18)
α-Diazoketones undergo smooth coupling with thiourea in the presence of 10 mol % of copper(II) triflate to produce the corresponding 2-aminothiazoles in excellent yields with high selectivity. The use of copper(II) triflate makes this method simple, convenient and practical. This method works well with both aryl and alkyl diazoketones to furnish a wide range of 2-aminothiazoles.
N-isocyanotriphenyliminophosphorane; a convenient reagent for the conversion of acyl chlorides into α-diazoketones
Aller, Enrique,Molina, Pedro,Lorenzo, ángeles
, p. 526 - 528 (2007/10/03)
Aliphatic, aromatic and vinylic acid chlorides were converted into the corresponding α-diazoketones in synthetically useful yields by reaction with N-isocyanotriphenyliminophosphorane followed by treatment of the resulting N- unsubstituted α-ketohydrazido
