No abstract

In the reaction of N-aryl-2-nitrosoanilines with β-diketones, a condensation of the nitroso group with diketone carbanion followed by condensation of the amino function with the less crowded carbonyl group leads to 2-alkylidene-3-acyl-1,2-dihydroquinoxalines under mild basic conditions.

A novel route leading to 6-acylindolo[1,2-a]quinoxalines involving condensation of N-(2-iodoaryl)-2-nitrosoanilines with β-diketones followed by Heck cyclization is described.

SummaryAlkylation of 5-nitroindol-4-ylacetonitriles with ethyl chloroacetate, α-halomethyl ketones, and chloroacetonitrile followed by a treatment of the products with chlorotrimethylsilane in the presence of DBU gives 1-cyanopyrrolo[3,2-e]indoles substituted in position 2 with electron-withdrawing groups.

Alkylation of 2-nitrobenzyl cyanides with α-halomethyl ketones furnishes ketonitriles which upon reduction with tin(II) chloride form quinoline-4-carbonitriles in good yields.