Claisen-Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives with different substituents in H2 O/EtOH.

Abstract:

:A simple, green, and direct three-component condensation of acetophenone, aromatic aldehydes with 3-oxo-N-phenylbutanamide (acetoacetanilide) to generate some novel (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives was carried out over K2 CO3 (10 mol%) with high efficiency in water/ethanol as green solvent at room temperature. This protocol proceeded via Claisen-Schmidt condensation and Michael addition. The present methodology offers several advantages, such as short reaction time, high yield, more readily available and inexpensive materials, more environmentally friendly, no need for column chromatography, simple work-up procedure, and the absence of volatile and hazardous organic solvents.

journal_name

Chirality

journal_title

Chirality

authors

Mousavi SR

doi

10.1002/chir.22653

subject

Has Abstract

pub_date

2016-11-01 00:00:00

pages

728-736

issue

11

eissn

0899-0042

issn

1520-636X

journal_volume

28

pub_type

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