Synthesis of a peralkynylated pyrazino[2,3-g]quinoxaline

Shaobin Miao; Mark D Smith; Uwe H F Bunz

doi:10.1021/ol0529851

Synthesis of a peralkynylated pyrazino[2,3-g]quinoxaline

Org Lett. 2006 Feb 16;8(4):757-60. doi: 10.1021/ol0529851.

Authors

Shaobin Miao¹, Mark D Smith, Uwe H F Bunz

Affiliation

¹ School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, USA.

PMID: 16468760
DOI: 10.1021/ol0529851

Abstract

[structure: see text] The synthesis of a hexaethynyl[2,3-g]pyrazinoquinoxaline and its crystal structure are reported. Starting from tetraaminobenzoquinone, condensation to bis(triisopropylsilyl)hexadiyne-2,3-dione affords 2,3,7,8-tetrakis(triisopropylsilylethynyl)pyrazino[2,3-g]quinoxaline-5,10-dione. Reaction with TIPS-CC-Li followed by reduction with hypophosphite in the presence of KI furnished the title molecule in a yield of 62%. Pd catalysis is not involved in any of these steps.