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RESEARCH FRONT
Contents Vol 62(1)

Diversity-Oriented Synthesis of Substituted Furo[2,3-b]pyrazines

Vaibhav P. Mehta A , Sachin G. Modha A , Denis Ermolat’ev A , Kristof Van Hecke B , Luc Van Meervelt B and Erik V. Van der Eycken A C
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A Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium.

B Biomolecular Architecture, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium.

C Corresponding author. Email: erik.vandereycken@chem.kuleuven.be

Australian Journal of Chemistry 62(1) 27-41 https://doi.org/10.1071/CH08376
Submitted: 3 September 2008  Accepted: 25 October 2008   Published: 21 January 2009

Abstract

A highly efficient method for the synthesis of diversely substituted furo[2,3-b]pyrazines has been elaborated. The Ag+- or iodine-mediated electrophilic cyclization of readily generated 5-chloro-3-substituted ethynyl-1-(4-methoxybenzyl)-pyrazin-2(1H)-ones affords substituted furo[2,3-b]pyrazines, which undergo various palladium catalyzed reactions to generate a library of difficult to attain diversely substituted furo[2,3-b]pyrazines.


Acknowledgement

The authors thank the F.W.O. (Fund for Scientific Research – Flanders (Belgium)) and the Research Fund of the Katholieke Universiteit Leuven for financial support to the laboratory. D.E. is grateful to the Katholieke Universiteit Leuven for obtaining a scholarship. V.P.M. is grateful to the IRO (Interfacultaire Raad voor Ontwikkelingssamenwerking) for obtaining a doctoral scholarship. The authors thank Ir. B. Demarsin for HRMS measurements.


References


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