137117-06-7Relevant academic research and scientific papers
2-Oxindole Acts as a Synthon of 2-Aminobenzoyl Anion in the K2CO3-Catalyzed Reaction with Enones: Preparation of 1,4-Diketones Bearing an Amino Group and Their Further Transformations
Miao, Chun-Bao,Zeng, Yu-Mei,Shi, Tong,Liu, Rui,Wei, Peng-Fei,Sun, Xiao-Qiang,Yang, Hai-Tao
, p. 43 - 50 (2016)
A convenient approach for the synthesis of 1,4-diketones bearing an amino group has been developed through the K2CO3-catalyzed reaction of 2-oxindoles with enones with the assistance of atmospheric O2 via sequential Michael addition-oxidation-ring-cleavage process. The further intramolecular reaction leads to the formation of benzoazepinone, quinoline, and 3-oxindole derivatives.
LiBr-promoted photoredox neutral Minisci hydroxyalkylations of quinolines with aldehydes
Ji, Xiaochen,Liu, Qiong,Wang, Zhongzhen,Wang, Pu,Deng, Guo-Jun,Huang, Huawen
, p. 8233 - 8237 (2020/12/29)
Photoredox-neutral hydroxyalkylations of quinolines with aldehydes, induced by sustainable visible light under mild conditions, are described. Non-toxic and inexpensive LiBr is found to be the key for the success of the atom-economical Minisci method. Combined with a highly oxidative photocatalyst and visible light irradiation, the bromide additive mediates the H abstraction/acyl radical formation directly from aldehydes. The present mild photoredox neutral protocol provides an important alternative, especially for the challenging Minisci hydroalkylations, as well as a promising approach for atom-economical Minisci reactions with broader N-heterocycle spectra.
Unexpected domino reaction via Pd-catalyzed Sonogashira coupling of benzimidoyl chlorides with 1,6-enynes and cyclization to synthesize quinoline derivatives
Gao, Guo-Lin,Niu, Yan-Ning,Yan, Ze-Yi,Wang, Hong-Li,Wang, Gang-Wei,Shaukat, Ali,Liang, Yong-Min
supporting information; experimental part, p. 1305 - 1308 (2010/04/26)
(Chemical Equation Presented) A domino reaction via palladium-catalyzed Sonogashira coupling of benzimidoyl chlorides with 1,6-enynes and then cyclization to form quinoline derivatives has been developed. The reaction conditions and the scope of the process are examined, and a plausible mechanism is proposed. The procedure is simple, rapid, and general, and the substrates are readily available. 2010 American Chemical Society.
Studies on the Fischer Indole Synthesis: Rearrangements of Five-, Six- and Seven-membered Cyclic Hydrazones of Pyrazoline, Tetrahydropyridazine and Tetrahydro-1,2-diazepine Series in Polyphosphoric Acid
Benincori, Tiziana,Brenna, Elisabetta,Sannicolo, Franco
, p. 2139 - 2145 (2007/10/02)
The rearrangements of a few cyclic phenylhydrazones structurally related to 1-phenyl-Δ2-pyrazoline, 1-phenyl-1,4,5,6-tetrahydropyridazine, and 1-phenyl-4,5,6,7-tetrahydro-1,2-diazepine in hot polyphosphoric acid (PPA) are described.The five-membered-ring substrates (the pyrazolines) did not undergo the sigmatropic rearrangement typical of the Fischer indolization, the main reaction course being homolytic N-N bond cleavage, leading to benzidine and its 4-(2-benzoylethyl)-4'-(3-phenyl-Δ2-pyrazolin-1-yl) derivative.The six-membered heterocycles underwent two different reactions, both involving the tautomeric enehydrazine form: the first one is the sigmatropic rearrangement, expected for open-chain hydrazones, affording 4-acyl-1,2,3,4-tetrahydroquinoline derivatives; the second one is a retro-Diels-Alder reaction producing methyleneaniline and α,β-unsaturated carbonyl compounds.The seven-membered-ring substrate gave a 5-acyltetrahydrobenzazepine, resulting from the rearrangement, together with both a pyrrolidine and a pyrazine by-product; their formation involves homolytic N-N bond cleavage of the ring, a δ hydrogen abstraction, followed by intramolecular or intermolecular ring closure.Chemical proofs are given for the new structures.
