Structure of Reaction Products of Some Substituted Quinoxaline <i>N</i>-Oxides with Carbanions

Toman, Jaromír; Mindl, Jaromír; Lyčka, Antonín; Klicnar, Jiří; Srovnalová, Ivana; Koníček, Miloš

doi:10.1135/cccc19942493

CCCC > Archive > 1994, Volume 59 > Issue 11 > p. 2493

Structure of Reaction Products of Some Substituted Quinoxaline N-Oxides with Carbanions

Jaromír Toman^a, Jaromír Mindl^a, Antonín Lyčka^b, Jiří Klicnar^a, Ivana Srovnalová^a and Miloš Koníček^a

^a Department of Organic Chemistry, University of Pardubice, 532 10 Pardubice, Czech Republic
^b Research Institute of Organic Syntheses, 532 18 Pardubice-Rybitví, Czech Republic

Abstract

1,2,3-Triazolo[1,5-a]- (II) and 1,2,4-triazolo[4,3-a]quinoxaline 5-oxide (III) react with the carbanions of β-diketones and β-keto esters to give enaminones in the same way as their tetrazolo analogue. The difference in mechanism of reactions of these N-oxides with carbanions of 3-alkylpentane-2,4-dione and ethyl methyl acetoacetate giving aziridinopolyazoloquinoxalines and ethyl 2-(polyazoloquinoxalin-4-yl)propanoates, respectively, is discussed. It was shown that the reaction with carbanion including the aziridine ring closure proceeds with 3,4-dihydro-3-oxoquinoxaline-1-oxide as well.

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Structure of Reaction Products of Some Substituted Quinoxaline N-Oxides with Carbanions

Abstract