Synthesis of 3 H -pyrazoles by reaction of methyl and p -tolyl phenylethynyl sulfones with diphenyldiazomethane and their thermal and acid-catalyzed transformations
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| 024 | 7 | 0 | |a 10.1134/S107042801506010X |2 doi |
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| 245 | 0 | 0 | |a Synthesis of 3 H -pyrazoles by reaction of methyl and p -tolyl phenylethynyl sulfones with diphenyldiazomethane and their thermal and acid-catalyzed transformations |h [Elektronische Daten] |c [V. Vasin, Yu. Masterova, E. Bezrukova, V. Razin, N. Somov] |
| 520 | 3 | |a Methyl and p-tolyl phenylethynyl sulfones reacted with diphenyldiazomethane in diethyl ether at 20°C to give 1,3-dipolar cycloaddition products both according and contrary to the von Auwers rule, sulfonylsubstituted 3H-pyrazoles at a ratio of 1: 1.5 and 1.3: 1, respectively. On heating in toluene for 2 h, the Auwers adducts underwent van Alphen-Hüttel rearrangement with 1,5-sigmatropic shift of one phenyl substituent to afford sulfonyl-substituted 4H-pyrazoles. Under analogous conditions, the anti-Auwers adducts rearranged into sulfonyl-substituted N-phenyl-1H-pyrazoles containing a small amount of the denitrogenation product, sulfonyl-substituted cyclopropene. The Auwers adducts, as well as 4H-pyrazoles resulting from their thermal rearrangement, were converted in 5-7 days at 20°C into 3,4,4-triphenyl-1H-pyrazol-5(4H)-one by the action of a catalytic amount of sulfuric acid in acetic acid. Under analogous conditions, the regioisomeric anti-Auwers adducts gave rise to 3,4,5-triphenyl-1H-pyrazole with an impurity of 4-(R-sulfonyl)-1,3,5-triphenyl-1H-pyrazoles. | |
| 540 | |a Pleiades Publishing, Ltd., 2015 | ||
| 700 | 1 | |a Vasin |D V. |u Ogarev Mordovian State University, ul. Bol'shevistskaya 68, 430005, Saransk, Russia |4 aut | |
| 700 | 1 | |a Masterova |D Yu |u Ogarev Mordovian State University, ul. Bol'shevistskaya 68, 430005, Saransk, Russia |4 aut | |
| 700 | 1 | |a Bezrukova |D E. |u Ogarev Mordovian State University, ul. Bol'shevistskaya 68, 430005, Saransk, Russia |4 aut | |
| 700 | 1 | |a Razin |D V. |u St. Petersburg State University, Universitetskii pr. 26, 198504, St. Petersburg, Russia |4 aut | |
| 700 | 1 | |a Somov |D N. |u Lobachevsky State University of Nizhni Novgorod, pr. Gagarina 23, 603950, Nizhni Novgorod, Russia |4 aut | |
| 773 | 0 | |t Russian Journal of Organic Chemistry |d Pleiades Publishing |g 51/6(2015-06-01), 874-883 |x 1070-4280 |q 51:6<874 |1 2015 |2 51 |o 11178 | |
| 856 | 4 | 0 | |u https://doi.org/10.1134/S107042801506010X |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/S107042801506010X |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Vasin |D V. |u Ogarev Mordovian State University, ul. Bol'shevistskaya 68, 430005, Saransk, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Masterova |D Yu |u Ogarev Mordovian State University, ul. Bol'shevistskaya 68, 430005, Saransk, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Bezrukova |D E. |u Ogarev Mordovian State University, ul. Bol'shevistskaya 68, 430005, Saransk, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Razin |D V. |u St. Petersburg State University, Universitetskii pr. 26, 198504, St. Petersburg, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Somov |D N. |u Lobachevsky State University of Nizhni Novgorod, pr. Gagarina 23, 603950, Nizhni Novgorod, Russia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Russian Journal of Organic Chemistry |d Pleiades Publishing |g 51/6(2015-06-01), 874-883 |x 1070-4280 |q 51:6<874 |1 2015 |2 51 |o 11178 | ||