Abstract:
The sequential reaction of ketones with phenylacetylene in the presence of KOH/DMSO system followed by the treatment of the reaction mixture with HCl and monosubstituted hydrazines leads to pyrazolines and pyrazoles in up to 87% total yield.
Citation:
E. Yu. Schmidt, E. V. Ivanova, N. V. Semenova, I. V. Tatarinova, I. A. Ushakov, B. A. Trofimov, “Base-catalyzed α-vinylation of ketones with acetylenes as a key step in one-pot synthesis of pyrazolines and pyrazoles”, Mendeleev Commun., 25:2 (2015), 131–132
Linking options:
https://www.mathnet.ru/eng/mendc2324
https://www.mathnet.ru/eng/mendc/v25/i2/p131
This publication is cited in the following 12 articles:
G R Gnatovsky, V B Orel, N M Vitkovskaya, “The addition of ethylhydrazine to α,β- and β,γ-unsaturated ketones: a quantum-chemical modeling”, J. Phys.: Conf. Ser., 1847:1 (2021), 012052
Rahul P., Nitha P. R., Vishnu K. Omanakuttan, Sheba Ann Babu, P. Sasikumar, Vakayil K. Praveen, Henning Hopf, Jubi John, “Superbase‐Mediated Indirect Friedländer Reaction: A Transition Metal‐Free Oxidative Annulation toward Functionalized Quinolines”, Eur J Org Chem, 2020:20 (2020), 3081
Lun Li, Kimberly A. Wasik, Brian J. Frost, Laina M. Geary, “Silver catalyzed proto- and sila-Nakamura-type α-vinylation of silyl enol ethers with dichloroacetylene. Divergent formation of stereochemically pure tri- and tetrasubstituted olefins”, Tetrahedron Letters, 61:2 (2020), 151370
Vladimir B. Orel, Nadezhda M. Vitkovskaya, Vladimir B. Kobychev, Boris A. Trofimov, “Transition-Metal-Free C-Vinylation of Ketones with Acetylenes: A Quantum-Chemical Rationalization of Similarities and Differences in Catalysis by Superbases MOH/DMSO and tBuOM/DMSO (M = Na, K)”, J. Org. Chem., 83:7 (2018), 3719
Boris A. Trofimov, Elena Yu. Schmidt, “Acetylenes in the Superbase-Promoted Assembly of Carbocycles and Heterocycles”, Acc. Chem. Res., 51:5 (2018), 1117
E. Yu. Schmidt, I. A. Bidusenko, N. A. Cherimichkina, B. A. Trofimov, “Acetylene as driving and organizing molecule in the assembling reactions with chalcones in the NaOBut/DMSO superbase system”, Mendeleev Commun., 28:1 (2018), 47–48
Elena Yu. Schmidt, Inna V. Tatarinova, Nadezhda I. Protsuk, Igor' A. Ushakov, Boris A. Trofimov, “A One-Pot Synthesis of 2-Aminopyrimidines from Ketones, Arylacetylenes, and Guanidine”, J. Org. Chem., 82:1 (2017), 119
E. Yu. Schmidt, I. V. Tatarinova, E. V. Ivanova, B. A. Trofimov, “2-Aminopyrimidines in just two steps from ketones, acetylenes and guanidine via β,γ enones”, Mendeleev Commun., 27:3 (2017), 283–284
A. V. Popov, V. A. Kobelevskaya, L. I. Larina, G. G. Levkovskaya, “Synthesis of 3-(5-chloropyrazol-3-yl)propenals”, Mendeleev Commun., 27:2 (2017), 178–179
B. A. Trofimov, K. V. Belyaeva, L. V. Andriyankova, L. P. Nikitina, A. G. Mal'kina, “Ring-opening of pyridines and imidazoles with electron-deficient acetylenes: En route to metal-free organic synthesis”, Mendeleev Commun., 27:2 (2017), 109–115
E. Yu. Schmidt, I. V. Tatarinova, I. A. Ushakov, B. A. Trofimov, “Base-catalyzed cascade dimerization of γ-aryl-β,γ-enones into acylated terphenyls”, Mendeleev Commun., 26:5 (2016), 378–379
Alexander V. Artem'ev, Svetlana F. Malysheva, Nataliya A. Belogorlova, Nadezhda I. Protzuk, Alexander I. Albanov, Irina Yu. Bagryanskaya, Elena Yu. Schmidt, Nina K. Gusarova, Boris A. Trofimov, “An Expedient Access to γ‐Ketophosphine Chalcogenides via the Chemo‐ and Regioselective Addition of Secondary Phosphine Chalcogenides to β,γ‐Ethylenic Ketones”, Heteroatom Chemistry, 26:6 (2015), 455
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