Reaction of benzofurazan 1-oxide with 1-(2-naphthyl)-and 1-hetaryl-butane-1,3-diones; preparation of aryl and hetaryl 2-quinoxalinyl ketones

Add time:08/20/2019    Source:sciencedirect.com

Aryl (4-methoxyphenyl and 2-naphthyl) and hetaryl (2-furyl, 3-pyridyl, and 2-thienyl) 3-methyl-2-quinoxalinyl ketones were prepared via the reaction of benzofurazan 1-oxide (BFO) with 1-aryl- and 1-hetaryl-butane-1,3-diones, followed by reduction of the resulting aryl or hetaryl 3-methyl-2-quinoxalinyl ketone 1,4-dioxides with sodium dithionite. 1-(2-Furyl)butane-1,3-dione and 1-(2-pyridyl)butane-1,3-dione yielded 2-acetyl-3-(2-furyl)quinoxaline 1,4-dioxide and 2-acetyl-3-(2-pyridyl)quinoxaline 1,4-dioxide respectively as minor products on reaction with BFO. The effect of the structure of the hetaryl (or aryl) group in the 1,3-diketone on the reaction with BFO is reported.

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