Abstract:
Acetylene in the KOH / DMSO system (1 bar, 140 °C, 12 h) is annulated with 3-methyl-7,8-dihydrocinnolin-5(6H)-one oxime in several directions: along with the building up of pyrrole fragment over cyclohexane ring, transformation of the oxime function to the amino one occurs. This amine undergoes other annulations to form tricyclic compounds with pyridine moieties.
Citation:
O. V. Petrova, L. N. Sobenina, I. A. Ushakov, A. B. Budaev, A. V. Ivanov, V. A. Samsonov, A. Ya. Tikhonov, B. A. Trofimov, “Multi-channel annulation of acetylene with 3-methyl-7,8-dihydrocinnolin-5(6H)-one oxime in the KOH/DMSO superbasic system”, Mendeleev Commun., 27:4 (2017), 344–345
Linking options:
https://www.mathnet.ru/eng/mendc1988
https://www.mathnet.ru/eng/mendc/v27/i4/p344
This publication is cited in the following 6 articles:
A. V. Ivanov, V. S. Shcherbakova, L. N. Sobenina, “Substituted pyrroles based on ketones: prospects of application and advances in synthesis”, Russian Chem. Reviews, 92:9 (2023), RCR5090
Andrey V. Ivanov, Svetlana V. Martynovskaya, Victoria S. Shcherbakova, Igor A. Ushakov, Tatyana N. Borodina, Alexander S. Bobkov, Nadezhda M. Vitkovskaya, “Ambient access to a new family of pyrrole-fused pyrazine nitrones via 2-carbonyl-N-allenylpyrroles”, Org. Chem. Front., 7:24 (2020), 4019
A. B. Budaev, A. V. Ivanov, O. V. Petrova, V. A. Samsonov, I. A. Ushakov, A. Ya. Tikhonov, L. N. Sobenina, B. A. Trofimov, “1,2,5-Oxadiazolo[3,4-g]indoles via annelation of 6,7-dihydrobenzo[c][1,2,5]oxadiazol-4(5H)-one oxime with acetylene”, Mendeleev Commun., 29:1 (2019), 53–54
Vladimir V. Voronin, Maria S. Ledovskaya, Alexander S. Bogachenkov, Konstantin S. Rodygin, Valentine P. Ananikov, “Acetylene in Organic Synthesis: Recent Progress and New Uses”, Molecules, 23:10 (2018), 2442
E. Yu. Schmidt, I. V. Tatarinova, N. I. Protsuk, I. A. Ushakov, B. A. Trofimov, “Dioximes of 1,6-heptanediones from acetylene and ketones: only three atom-economic steps”, Mendeleev Commun., 28:2 (2018), 143–144
E. Yu. Schmidt, I. V. Tatarinova, I. A. Ushakov, B. A. Trofimov, “2,4,6-Trisubstituted 3,4-dihydropyrans from acetylene and ketones: deacetylation in the KOBut/DMSO system”, Mendeleev Commun., 28:2 (2018), 145–146
Contact us: