A novel palladium-catalyzed synthesis of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones

Björn C G Söderberg; Jeffery M Wallace; Joaquín Tamariz

doi:10.1021/ol025640g

A novel palladium-catalyzed synthesis of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones

Org Lett. 2002 Apr 18;4(8):1339-42. doi: 10.1021/ol025640g.

Authors

Björn C G Söderberg¹, Jeffery M Wallace, Joaquín Tamariz

Affiliation

¹ Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045, USA. bjorn.soderberg@mail.wvu.edu

PMID: 11950357
DOI: 10.1021/ol025640g

Abstract

Reactions of enamines, derived from 2-nitroanilines and alpha-substituted aldehydes, with carbon monoxide (6 atm) in the presence of a catalytic amount of bis(dibenzylideneacetone)palladium(0) (Pd(dba)(2)) and 1,3-bis(diphenylphosphino)propane (dppp) afford readily separated mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones. Addition of a catalytic amount of 1,10-phenanthroline to the reaction mixture substantially improved the yield of products. [reaction: see text]

Publication types

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

MeSH terms

Carbon Monoxide / chemistry
Catalysis
Crystallography, X-Ray
Indicators and Reagents
Oxidation-Reduction
Palladium / chemistry*
Quinoxalines / chemical synthesis*

Substances

Indicators and Reagents
Quinoxalines
Palladium
Carbon Monoxide

Grants and funding

R15 GM 51030/GM/NIGMS NIH HHS/United States