Reactions of spirocyclopropane-containing 1- and 2-pyrazolines with electrophilic reagents |
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Authors: | Yu V Tomilov I V Kostyuchenko G P Okonnishnikova E V Shulishov E A Yagodkin O M Nefedov |
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Institution: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation
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Abstract: | Hydrochlorination of spiro(1-pyrazoline-3,1′-cyclopropanes) proceeds regioselectively at the azocyclopropane group to form 3-(2-haloethyl)pyrazoline derivatives. If the latter contain a halogen atom in the heterocycle, they are readily converted into (2-haloethyl)pyrazole hydrohalides. Bromination of 3-cyanospiro(2-pyrazoline-5,1′-cyclopropane) withN-bromosuccinimide at 20°C proceeds with retention of the cyclopropane ring to form 3-bromo-3-cyanospiro(1-pyrazoline-5,1′-cyclopropane), which is converted into (2-bromoethyl)cyanopyrazole in ∼60% yield at ∼20°C after 3–4 days. |
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