Tandem intramolecular cyclisation/1,3-aryl shift in N-(4,4-diethoxybutyl)-1-arylmethanimines (Kazan reaction): synthesis of 3-benzylidene-1-pyrrolines was written by Smolobochkin, A. V.;Gazizov, A. S.;Melyashova, A. S.;Voronina, J. K.;Strelnik, A. G.;Vatsadze, S. Z.;Burilov, A. R.;Pudovik, M. A.;Fedorova, O. A.;Sinyashin, O. G.. And the article was included in RSC Advances in 2017.Electric Literature of C6H5ClO2 The following contents are mentioned in the article:
In this article, a novel tandem reaction, which transformed N-(4,4-diethoxybutyl)imines into 3-arylidene-1-pyrrolines, was described. The substrate scope of the starting acetals included arenes with electron-donating and withdrawing groups. The X-ray study of products confirmed the E-stereochem. of the double bonds formed. The best yields (99%) were found in boiling xylene in the presence of TsOH (or 2-nitroresocinol) during 40 (50) hours. The study of substituents effect on the course of the reaction revealed that cascade process took place, combining acid-catalyzed intramol. cyclization of N-(4,4-diethoxybutyl)imines and unusual 1,3-sigmatropic shift of the aryl fragment. Cyclic imines that were formed in high/excellent yields were of interest both from the viewpoint of their biol. activity and synthetic usefulness. This study involved multiple reactions and reactants, such as 4-Chlororesorcinol (cas: 95-88-5Electric Literature of C6H5ClO2).
4-Chlororesorcinol (cas: 95-88-5) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Electric Literature of C6H5ClO2
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics