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Paper | Regular issue | Vol 57, No. 1, 2002, pp.97-110
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9371
Preparation of Thieno[2,3-b]pyrazines as Bioisosteres for Quinoxaline Derivatives wiht Reverse Transcriptase Inhibition

Thomas Erker* and Karin Trinkl

*Institute of Pharmaceutical Chemistry, University of Vienna, Pharmaziezentrum, Althanstrsse 14, A-1090 Vienna, Austria


Replacement of the fused aromatic moiety in GW-420867X, a HIV-1 specific nonnucleoside reverse transcriptase inhibitor, with thiophene provided 2-oxo-1,2,3,4-tetrahydrothieno[2,3-b]pyrazine derivatives. The synthesis starts with the reaction of 5-acyl-2-chloro-3-nitrothiophene and different amino acid derivatives. The resulting substitution products are reduced, cyclized and N-acylated to give the desired compounds (27 - 33).