caa a22 4500 475760336 CHVBK 20180406123549.0 cr unu---uuuuu 170329e20000301xx s 000 0 eng 10.1007/BF02494777 doi (NATIONALLICENCE)springer-10.1007/BF02494777 Reactions of spirocyclopropane-containing 1- and 2-pyrazolines with electrophilic reagents [Elektronische Daten] [Yu. Tomilov, I. Kostyuchenko, G. Okonnishnikova, E. Shulishov, E. Yagodkin, O. Nefedov] 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. Kluwer Academic/Plenum Publishers, 2000 spiro(1-pyrazoline-3,1′-cyclopropanes) nationallicence spiro(2-pyrazoline-5,1′-cyclopropanes) nationallicence 3-(2-haloethyl)pyrazolines and 3-(2-haloethyl)pyrazoles nationallicence hydrochlorination nationallicence acylation nationallicence bromination with N -bromosuccinimide nationallicence Tomilov Yu N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Kostyuchenko I. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Okonnishnikova G. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Shulishov E. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Yagodkin E. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Nefedov O. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/3(2000-03-01), 472-477 1066-5285 49:3<472 2000 49 11172 https://doi.org/10.1007/BF02494777 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02494777 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Tomilov Yu N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Kostyuchenko I. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Okonnishnikova G. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Shulishov E. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Yagodkin E. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Nefedov O. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/3(2000-03-01), 472-477 1066-5285 49:3<472 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer