Divergent Behavior of β-Carbonyl-Substituted 1H-Benzo[f]chromenes Under Henry Reaction Conditions

Abstract

A series of β-carbonyl-substituted 1H-benzo[f]chromenes has been introduced into the reaction with nitromethane in the presence of ammonium acetate. It has been shown that in the case of 1H-benzo[f]chromene-2-carbaldehydes, the reaction does not stop at the formation of the classical Henry reaction products − β-nitroalcohols, but their dehydration to nitrovinylchromenes takes place. In the case of alkyl(benzochromen-2-yl)ketones, 3-alkyl-2-(2-nitrovinyl)-1H-benzo[f]chromenes are formed, and methoxalyl-substituted benzochromenes give 10-amino-7a,8-dihydrobenzo[5,6]chromeno[2,3-b]pyrrol-9(11H)-ones under the Henry reaction conditions. © 2025 Wiley-VCH GmbH.