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Synthesis 2011(9): 1419-1426  
DOI: 10.1055/s-0030-1259973
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Three-Component Synthesis of Quinoxaline, Quinazoline, and Phenazine Ring Systems Using Fischer Carbene Complexes

Soumita Mukherjee, Priyabrata Roy, Binay K. Ghorai*
Department of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
Fax: +91(33)26682916; e-Mail: bkghorai@yahoo.co.in;
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Publikationsverlauf

Received 9 December 2010
Publikationsdatum:
25. März 2011 (online)

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Abstract

One-pot, three-component synthesis of nitrogen-containing polycyclic heterocycles bearing two nitrogen atoms such as quinoxaline, quinazoline, and phenazine derivatives by the coupling of appropriate vicinal alkynylheteroaryl carbonyl derivatives with Fischer­ carbene complexes and dienophiles has been investigated. This involves the generation of furo[3,4-b]pyrazines, furo[3,4-d]pyrimidines, and furo[3,4-b]quinoxalines as transient intermediates, which were trapped with suitable Diels-Alder dienophiles in an inter- or intramolecular fashion.

Key words

azaisobenzofuran - quinoxaline - quinazoline - phenazine - Diels-Alder reaction - carbene complexes

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