Three-component reaction and organocatalysis in one: synthesis of densely substituted 4-aminochromanes

By Jan Svĕtlík, Nad'a Prónayová, Vladimír Frecer, Dariusz Cież

July 28, 2017

  • Year

  • Technique

  • Industry

Title

Three-component reaction and organocatalysis in one: synthesis of densely substituted 4-aminochromanes

Author

Jan Svĕtlík, Nad'a Prónayová, Vladimír Frecer, Dariusz Cież

Year

2016

Journal

Tetrahedron

Abstract

Cyclocondensation of salicylaldehydes with alkyl acetoacetates and 2-aminobenzothiazoles or 2-amino-thiadiazole/thiazoles under L-proline catalysis gives 4-hetarylamino substituted chromanecarboxylate derivatives. The mechanism involving the Mannich/hemiketalization cascade reaction and the observed stereoselectivity of the three component process are discussed.

Full Article

http://www.sciencedirect.com/science/article/pii/S0040402016310419

Instrument

J-815

Keywords

Circular dichroism, Stereochemistry, Pharmaceutical