Reaction of esters of 2-arylcyclo-propanecarboxylic acids with nitrous acid. Synthesis of aryl-substituted 3-ethoxycarbonyl-4, 5-dihydroisoxazoles and 3- …

AZ Kadzhaeva, EV Trofimova, AN Fedotov…

Index: Kadzhaeva; Trofimova; Fedotov; Potekhin; Gazzaeva; Mochalov; Zefirov Chemistry of Heterocyclic Compounds, 2009 , vol. 45, # 5 p. 595 - 605

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Citation Number: 2

Abstract

Esters of 2-arylcyclopropanecarboxylic acids react with nitrous acid generated in situ with regioselective insertion of the nitrosyl cation into the cyclopropane ring. Depending on the substrate/nitrosylating agent ratio, the reaction proceeds with the formation of either aryl- substituted 3-ethoxycarbonyl-4, 5-dihydroisoxazoles or the corresponding isoxazoles. The nature and position of the substituents in the aromatic ring of the starting 2- ...