Journal of Organic Chemistry p. 8283 - 8288 (1995)
Update date:2022-08-30
Topics:
Pohmer, Joerg
Lakshmikantham, M. V.
Cava, Michael P.
The highly reactive o-quinonoid heterocycles thieno<3,4-b>quinoxaline (1a) and its 6,7-dimethyl derivative (1b) have been synthesized by a base-catalyzed Pummerer reaction and isolated in crystalline form.In contrast, the 1,3-dibromothieno<3,4-b>quinoxaline (8) could be characterized in solution but not isolated in pure form.The readily prepared 1,3-dihydrothieno<3,4-b>quinoxaline (5a) underwent a direct Knoevenagel condensation with thiophene-2-carboxaldehyde to give the stilbenoid 14a.Sulfide 5a was also converted in a two-step process to the stable 1,3-diformylthieno<3,4-b>quinoxaline 11a.
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