Reaction of esters of 2-arylcyclo-propanecarboxylic acids with nitrous acid. Synthesis of aryl-substituted 3-ethoxycarbonyl-4,5-dihydroisoxazoles and 3-ethoxycarbonylisoxazoles |
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Authors: | A Z Kadzhaeva E V Trofimova A N Fedotov K A Potekhin R A Gazzaeva S S Mochalov N S Zefirov |
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Institution: | (1) K. L. Khetagurov North Ossetian State University, 46 Vatutin St., Vladikavkaz, 362000, Russia;(2) M. V. Lomonosov Moskow State University, 1-3 Leninskiye Gory, Moscow, 119991, Russia |
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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. |
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