A new example of reversible thermal isomerization of 3 H -pyrazole into 4 H -pyrazole
| LEADER | caa a22 4500 | ||
|---|---|---|---|
| 001 | 605530076 | ||
| 003 | CHVBK | ||
| 005 | 20210128100821.0 | ||
| 007 | cr unu---uuuuu | ||
| 008 | 210128e20151001xx s 000 0 eng | ||
| 024 | 7 | 0 | |a 10.1134/S1070428015100103 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1134/S1070428015100103 | ||
| 245 | 0 | 2 | |a A new example of reversible thermal isomerization of 3 H -pyrazole into 4 H -pyrazole |h [Elektronische Daten] |c [V. Vasin, V. Razin, Yu. Markelova, Yu. Masterova] |
| 520 | 3 | |a 9-Diazofluorene reacted with phenyl prop-1-yn-1-yl sulfone in diethyl ether at 20°C (3-4 days) to give 5'-(benzenesulfonyl)-4'-methylspiro[fluorene-9,3'-pyrazole] (3H-pyrazole) as the only 1,3-dipolar cycloaddition product formed according to the von Auwers rule. On heating in boiling ethanol for 0.5 h, 5'-(benzenesulfonyl)-4'-methylspiro[fluorene-9,3'-pyrazole] underwent partial reversible isomerization into a 4H-pyrazole derivative, 3-(benzenesulfonyl)-3a-methyl-3aH-dibenzo[e,g]indazole, whereas in toluene at 180°C (40 min) it was completely converted into thermodynamically more stable 2-(benzenesulfonyl)-3-methylpyrazolo[1,5-f]phenanthridine with a 1H-pyrazole fragment. 3a-Methyl-2H-dibenzo[e,g]indazol-3(3aH)-one was formed when the 3H- and 4H-pyrazoles were kept in glacial acetic acid at 20°C in the presence of a catalytic amount of sulfuric acid, followed by treatment with water. Alcoholic potassium hydroxide promoted reversible isomerization of the 3H-pyrazole into 5'-(benzenesulfonyl)-4'-methylidene-2',4'-dihydrospiro[ fluorene-9,3'-pyrazole]. | |
| 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 Razin |D V. |u St. Petersburg State University, Universitetskii pr. 26, 198504, St. Petersburg, Russia |4 aut | |
| 700 | 1 | |a Markelova |D Yu |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 | |
| 773 | 0 | |t Russian Journal of Organic Chemistry |d Pleiades Publishing |g 51/10(2015-10-01), 1418-1422 |x 1070-4280 |q 51:10<1418 |1 2015 |2 51 |o 11178 | |
| 856 | 4 | 0 | |u https://doi.org/10.1134/S1070428015100103 |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/S1070428015100103 |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 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 Markelova |D Yu |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 773 |E 0- |t Russian Journal of Organic Chemistry |d Pleiades Publishing |g 51/10(2015-10-01), 1418-1422 |x 1070-4280 |q 51:10<1418 |1 2015 |2 51 |o 11178 | ||