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Synthesis 2010(10): 1599-1602  
DOI: 10.1055/s-0029-1218715
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Unexpected Pyrrolo[2,3-b]quinoxaline-2-carbaldehydes via Sonogashira Coupling Reaction

Ali Keivanloo*, Mohammad Bakherad, Amin Rahimi
School of Chemistry, Shahrood University of Technology, Shahrood, Iran
Fax: +98(273)3395441; e-Mail: akeivanloo@yahoo.com; e-Mail: keivanloo@shahroodut.ac.ir;
Further Information

Publication History

Received 6 January 2010
Publication Date:
24 March 2010 (online)

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Abstract

The reaction of a number of N-alkyl-3-chloroquinoxaline-2-amines with propargyl bromide in the presence of PdCl2(PPh3)2 and copper(I) iodide in wet morpholine leads to the formation of the unexpected N-substituted pyrrolo[2,3-b]quinoxaline-2-carbaldehydes in good yields. A possible mechanism for the conversion is suggested.

Key words

palladium catalyst - pyrroloquinoxaline - Sonogashira coupling - propargyl bromide

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