96498-78-1Relevant articles and documents
An Electrochemical Route for Special Oxidative Ring-Opening of Indoles
Qin, Hong,Yang, Zhao,Zhang, Zhen,Liu, Chengkou,He, Wei,Fang, Zheng,Guo, Kai
supporting information, p. 13024 - 13028 (2021/08/09)
A novel electrochemical protocol for the oxidative cleavage of indoles has been developed, which o?ers a simple way to access synthetically useful anthranilic acid derivatives. In undivided cells, a wide variety of indoles and alcohol compounds are examined to a?ord amide ester aromatics without using extra oxidants and stoichiometric metal catalysts, which avoids the formation of undesired by-products and exhibits high atom economy. The products we described in this perspective represent a synthetic intermediate in numerous drug molecules and industrial chemical reagents and remarkably show potential application in the future.
The Chemistry of 2-Aminobenzoyl Hydrazides. 1. Effects of Orthoester Substituents on the Mode of Cyclization
Leiby, Robert W.
, p. 1825 - 1832 (2007/10/02)
Treatment of substituted 2-aminobenzoyl hydrazides with orthoesters has been found to yield different products depending upon the type of orthoester employed.Equimolar quantities of orthoester and hydrazide yield 3-amino-4(3H)-quinazolinones, whereas utilization of a two-fold excess (or greater) of orthoester yields, in some cases, 3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones as minor products in addition to N-imidate esters as major products.Treatment of hydrazides with trimethyl orthobenzoate yields substituted 5-(2-aminophenyl)-1,3,4-oxadiazoles and 3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones.The steric bulk of the phenyl group in trimethyl orthobenzoate effects the formation of adduct at the β-nitrogen of the hydrazide which cyclized to the oxadiazole and benzotriazepinone products.In the aliphatic orthoester series, the formation of adduct to the aromatic amino group appears to be favored which gives rise to quinazolinone and benzotriazepinone products.