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
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| 024 | 7 | 0 | |a 10.1134/S1070428015080138 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1134/S1070428015080138 | ||
| 245 | 0 | 0 | |a 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 |h [Elektronische Daten] |c [V. Vasin, V. Razin, E. Bezrukova, D. Korovin, P. Petrov, N. Somov] |
| 520 | 3 | |a 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. | |
| 540 | |a Pleiades Publishing, Ltd., 2015 | ||
| 700 | 1 | |a Vasin |D V. |u Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia |4 aut | |
| 700 | 1 | |a Razin |D V. |u St. Petersburg State University, St. Petersburg, Russia |4 aut | |
| 700 | 1 | |a Bezrukova |D E. |u Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia |4 aut | |
| 700 | 1 | |a Korovin |D D. |u Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia |4 aut | |
| 700 | 1 | |a Petrov |D P. |u Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia |4 aut | |
| 700 | 1 | |a Somov |D N. |u Lobachevskii Nizhny Novgorod State University, Nizhny Novgorod, Russia |4 aut | |
| 773 | 0 | |t Russian Journal of Organic Chemistry |d Pleiades Publishing |g 51/8(2015-08-01), 1144-1154 |x 1070-4280 |q 51:8<1144 |1 2015 |2 51 |o 11178 | |
| 856 | 4 | 0 | |u https://doi.org/10.1134/S1070428015080138 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1134/S1070428015080138 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Vasin |D V. |u Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Razin |D V. |u St. Petersburg State University, St. Petersburg, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Bezrukova |D E. |u Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Korovin |D D. |u Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Petrov |D P. |u Ogarev Mordovian State University, Bolshevistskaya ul. 68, 430005, Saransk, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Somov |D N. |u Lobachevskii Nizhny Novgorod State University, Nizhny Novgorod, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Russian Journal of Organic Chemistry |d Pleiades Publishing |g 51/8(2015-08-01), 1144-1154 |x 1070-4280 |q 51:8<1144 |1 2015 |2 51 |o 11178 | ||