Reactions of Substituted Ethyl 1,2,3,4,4′,5′-Hexahydrospiro-[naphthalene-2,5′-pyrazole]-3′-carboxylates with Halogens

Author： Molchanov A.   Korotkov V.   Kopf J.   Kostikov R.  

Publisher： MAIK Nauka/Interperiodica

ISSN： 1070-4280

Source： Russian Journal of Organic Chemistry, Vol.41, Iss.7, 2005-07, pp. : 1036-1042

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Abstract

Substituted ethyl 1,2,3,4,4′,5′-hexahydrospiro[naphthalene-2,5′-pyrazole]-3′-carboxylates react with chlorine or N-bromosuccinimide to give spirocyclic substituted 3-halo-4,5-dihydro-3H-pyrazoles which lose nitrogen molecule on heating with formation of substituted spirocyclic 1-halocyclopropane-1-carboxylates. Heating of the title compounds with bromine in acetic acid results in opening of the spiro-fused six-membered ring to afford ethyl 4-aryl-5-[2-(2-carboxyphenyl)ethyl]pyrazole-3-carboxylates.

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