REACTION OF ESTERS OF 2-ARYLCYCLOPROPANECARBOXYLIC ACIDS WITH NITROUS ACID. SYNTHESIS OF ARYL-SUBSTITUTED 3-ETHOXYCARBONYL-4,5-DIHYDROISOXAZOLES AND 3-ETHOXYCARBONYLISOXAZOLES

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-arylcyclopropanecarboxylic acid esters affect the reaction rate but have no effect on the regioselectivity of the attack by the nitrosyl cation on the three-membered ring. A dependence of the reactivity of isomeric substrates on their stereochemistry and position of the nitro group in the aromatic ring is noted for 2- and 4-nitrophenyl derivatives of esters of cis- and trans-2-arylcyclopropanecarboxylic acids.

How to Cite
Kadzhaeva, A. Z.; Trofimova, E. V.; Fedotov, A. N.; Potekhin, K. A.; Gazzaeva, R. A.; Mochalov, S. S.; Zefirov, N. S.  Chem. Heterocycl. Compd. 2009, 45, 595. [Khim. Geterotsikl. Soedin. 2009, 753.]

For this article in the English edition see DOI 10.1007/s10593-009-0315-6