Details

Autor(en) / Beteiligte

• 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

Titel

Tandem intramolecular cyclisation/1,3-aryl shift in N-(4,4-diethoxybutyl)-1-arylmethanimines (Kazan reaction): synthesis of 3-benzylidene-1-pyrrolinesElectronic supplementary information (ESI) available: Synthetic procedures, characterization data and copies of NMR spectra for all compounds. CCDC 1544114-1544117. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7ra11216e

Erscheinungsjahr

2017-11

Link zum Volltext

Quelle

Free E-Journal (出版社公開部分のみ）

Beschreibungen/Notizen

• In this article, a novel tandem reaction, which transforms N -(4,4-diethoxybutyl)imines into 3-arylidene-1-pyrrolines, is described. The substrate scope of the starting acetals includes arenes with electron-donating and withdrawing groups. The X-ray study of products confirmed the E -stereochemistry of the double bonds formed. The best yields (99%) are 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 takes place, combining acid-catalyzed intramolecular cyclization of N -(4,4-diethoxybutyl)imines and unusual 1,3-sigmatropic shift of the aryl fragment. Cyclic imines that are formed in high/excellent yields are of interest both from the viewpoint of their biological activity and synthetic usefulness. A novel tandem reaction, which transforms N -(4,4-diethoxybutyl)imines to 3-arylidene-1-pyrrolines via intramolecular Mannich reaction/[1,3]-sigmatropic rearrangement of the aryl fragment is described.