A base-catalyzed solution-phase parallel synthesis of substituted vinylic benzamides from 3-amino-2-cyclohexanones

Alan J Anderson; Jesse M Nicholson; Oladapo Bakare; Ray J Butcher; K R Scott

doi:10.1021/cc0498837

A base-catalyzed solution-phase parallel synthesis of substituted vinylic benzamides from 3-amino-2-cyclohexanones

J Comb Chem. 2004 Nov-Dec;6(6):950-4. doi: 10.1021/cc0498837.

Authors

Alan J Anderson¹, Jesse M Nicholson, Oladapo Bakare, Ray J Butcher, K R Scott

Affiliation

¹ Department of Chemistry, Graduate School, Howard University, Washington, D.C. 20059, USA.

PMID: 15530123
DOI: 10.1021/cc0498837

Abstract

An improved method for the synthesis of benzamides from 3-amino-2-cyclohexenones is presented. Using sodium hydride, a base-catalyzed N-benzoylation provided significantly higher yields (71-79%) for the reported compounds. This novel protocol was applied in the solution-phase parallel synthesis of a 12-member library of vinylic benzamide derivatives of 3-amino-2-cyclohexenones in 63-90% yield, using a Radley's Carousel Reaction Station.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Benzamides / chemical synthesis*
Benzamides / chemistry
Catalysis
Combinatorial Chemistry Techniques / methods*
Cyclohexanones / chemistry*
Molecular Structure

Substances

Benzamides
Cyclohexanones

Abstract

Publication types

MeSH terms

Substances

Grants and funding