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Note | Regular issue | Vol 45, No. 12, 1997, pp.2449-2462
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7965
Syntheses in the Series of Pyrazolyl-substituted Quinoxalines

Barbara Matuszczak* and Kurt Mereiter

*Institute of Pharmaceutical Chemistry, University of Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria

Abstract

Starting from 3-(3-chloro-1H-pyrazol-5-yl)-1H-quinoxalin-2-one (2), a dihydroquinoxalinone derivative (6) was synthesised as potential HIV-1 reverse trans-criptase inhibitor. Moreover, a series of N4-[3-(3-pyrazolyl)-2-quinoxalinyl]-N1,N1-diethyl-1,4-pentanediamines (compounds of type B) and N-[3-(3-pyrazolyl)-2-quinoxalinyl]-N-(3-pyridyl)methylamines (11-13) — structurally related to antimalarial agents — could be prepared via the 2-chloro-3-[3(5)-chloro-1H-pyrazol-5(3)-yl]quinoxaline (7). The position of the alkyl substituent on the pyrazole nitrogen was determined unequivocally from NOE difference experiments or X-Ray structure analysis.