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Synthesis 2011(6): 943-953  
DOI: 10.1055/s-0030-1258432
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Characterization of Substituted Pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidines and Related Molecules

Antonio Fernández-Mato, Carlos Peinador*, José M. Quintela*
Departamento de Química Fundamental, Facultad de Ciencias, Universidade da Coruña, Campus A Zapateira, A Coruña 15008, Spain
Fax: +34(981)167065; e-Mail: carlos.peinador@udc.es; e-Mail: jose.maria.quintela@udc.es;
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Publication History

Received 14 December 2010
Publication Date:
10 February 2011 (online)

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Abstract

An efficient access for the synthesis of substituted pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidines and pyrazino[2′,3′:4,5]thieno[3,2-d]-1,2,3-triazines, heteroaromatic nitrogen ligands, is reported. The title compounds were obtained by functionalization of the corresponding chloro precursors, synthesized by reaction between 7-aminothieno[2,3-b]pyrazine-6-carbonitrile and N,N-dimethyldichloromethyleniminium chloride (Viehe’s salt) or sodium nitrite/hydrochloric acid, respectively. Moreover, this procedure provided a convenient synthetic route to bis(pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidines), functionalized molecules that are not readily available by other synthetic methods.

Key words

heterocycles - ligands - ring closure - antitumor agents - fused-ring systems

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