caa a22 4500 60553036X CHVBK 20210128100823.0 cr unu---uuuuu 210128e20150801xx s 000 0 eng 10.1134/S1070428015080138 doi (NATIONALLICENCE)springer-10.1134/S1070428015080138 Synthesis of 3,3-diphenyl-3 H -pyrazoles applying vinyl sulfones as chemical equivalents of acetylenes in reaction of 1,3-dipolar cycloaddition to diphenyldiazomethane [Elektronische Daten] [V. Vasin, V. Razin, E. Bezrukova, D. Korovin, P. Petrov, N. Somov] Vinyl phenyl sulfone, methyl (E)-3-(phenylsulfonyl)- and methyl (E)-3-(p-tosyl)acrylates, (E)-3-(phenylsulfonyl)- and (E)-3-(p-tosyl)acrylonitriles react in ethyl ether at 20°C with diphenyldiazomethane leading to the formation of the corresponding 5,5-diphenyl-3-(arylsulfonyl)- Δ2-pyrazolines. Products containing a methoxycarbonyl or cyano group at treating with DBU in dichloromethane at 0°C suffer a dehydrosulfonation and are converted into 4-substituted 3,3-diphenyl-3H-pyrazoles. The oxidation of the mentioned Δ2-pyrazolines with activated manganese dioxide in benzene at 20°C leads to the formation of 4-methoxycarbonyl- and 4-cyano-substituted 5-arylsulfonyl- 3,3-diphenyl-3H-pyrazoles respectively. The reactions of α-bromovinyl phenyl sulfones and a-bromovinyl methyl sulfones with diphenyldiazomethane afforded the corresponding 3-bromo- 5,5-diphenyl-3-sulfonyl-Δ1-pyrazolines. The first among them at 20°C suffered spontaneous elimination of molecular nitrogen and converted into 1-bromo-2,2-diphenyl-1-(phenylsulfonyl)cyclopropane whose structure was established by X-ray diffraction analysis. The action of DBU on another Δ1-pyrazoline resulted in the formation of the product of the Ramberg-Bäcklund reaction, 5-methylene-3,3-diphenyl-Δ1- pyrazoline together with the product of hydrodebromination-isomerization, 5,5-diphenyl-3-(methylsulfonyl)- Δ2-pyrazoline. Pleiades Publishing, Ltd., 2015 Vasin V. Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia aut Razin V. St. Petersburg State University, St. Petersburg, Russia aut Bezrukova E. Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia aut Korovin D. Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia aut Petrov P. Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia aut Somov N. Lobachevskii Nizhny Novgorod State University, Nizhny Novgorod, Russia aut Russian Journal of Organic Chemistry Pleiades Publishing 51/8(2015-08-01), 1144-1154 1070-4280 51:8<1144 2015 51 11178 https://doi.org/10.1134/S1070428015080138 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015080138 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Vasin V. Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia aut NATIONALLICENCE 700 1- Razin V. St. Petersburg State University, St. Petersburg, Russia aut NATIONALLICENCE 700 1- Bezrukova E. Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia aut NATIONALLICENCE 700 1- Korovin D. Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia aut NATIONALLICENCE 700 1- Petrov P. Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia aut NATIONALLICENCE 700 1- Somov N. Lobachevskii Nizhny Novgorod State University, Nizhny Novgorod, Russia aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/8(2015-08-01), 1144-1154 1070-4280 51:8<1144 2015 51 11178