Аннотация:
Chemo- and regioselective addition of anabasine to 3-(1-hydroxycyclohexyl)-2-propynenitrile in ethanol results in 52% yield of a monoadduct, (Z)-3-(1-hydroxycyclohexyl)-3-[2-(3-pyridinyl)piperidino]-2-propenenitrile: in this case, only the piperidine ring of anabasine takes part in the reaction. In acetonitrile, both piperidine and pyridine rings participate in the process giving a diadduct, (Z)-3-{2-[3-[(Z)-cyanomethylidene]-2-spirocyclohexyl-8aH-[1,3]oxazolo[3,2-a]pyridine-8(2H)-yl]piperidino}-3-(1-hydroxycyclohexyl)-2-propenenitrile in 68% yield.
Тип публикации:
Статья
Язык публикации: английский
Образец цитирования:
B. A. Trofimov, L. V. Andriyankova, R. T. Tlegenov, A. G. Mal'kina, A. V. Afonin, L. N. Il'icheva, L. P. Nikitina, “Reaction of anabasine with 3-(1-hydroxycyclohexyl)-2-propynenitrile: a new route to functionalised anabasine alkaloids”, Mendeleev Commun., 15:1 (2005), 33–35
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc3664
https://www.mathnet.ru/rus/mendc/v15/i1/p33
Эта публикация цитируется в следующих 26 статьяx:
Ludmila A. Oparina, Anton V. Kuzmin, Lyudmila A. Grishchenko, Nikita A. Kolyvanov, Igor' A. Ushakov, Boris A. Trofimov, “Reaction of acylpropargylic alcohols with 1-pyrrolines: A synthetic and quantum-chemical study”, Tetrahedron, 2025, 134566
Zeinolla Muldakhmetov, Serik Fazylov, Oral Nurkenov, Arstan Gazaliev, Akmaral Sarsenbekova, Irina Pustolaikina, Zhangeldy Nurmaganbetov, Olzhas Seilkhanov, Aisha A. Alsfouk, Eslam B. Elkaeed, Ibrahim H. Eissa, Ahmed M. Metwaly, “Combined Computational and Experimental Studies of Anabasine Encapsulation by Beta-Cyclodextrin”, Plants, 11:17 (2022), 2283
Boris A. Trofimov, Anastasiya G. Mal'kina, “Cyanoacetylenic Alcohols: Molecules of Interstellar Relevance in the Synthesis of Essential Heterocycles, Amino Acids, Nucleobases and Nucleosides”, Synthesis, 53:16 (2021), 2740
Andrei V. Afonin, Alexander V. Vashchenko, Alexander I. Albanov, Valentina V. Nosyreva, Anastasiya G. Mal'kina, Boris A. Trofimov, “Study of spontaneous E/Z isomerization of bis[(Z)‐cyanomethylidene]‐diazapentacyclodienedicarboxylates by 1H, 13C, and 15N NMR spectroscopy, X‐ray, and quantum chemical calculation data”, Magnetic Reson in Chemistry, 55:6 (2017), 563
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
Nina K. Gusarova, Pavel A. Volkov, Nina I. Ivanova, Svetlana N. Arbuzova, Kseniya O. Khrapova, Alexander I. Albanov, Vladimir I. Smirnov, Tatyana N. Borodina, Boris A. Trofimov, “One-pot reductive N-vinylation and C(4)-phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides”, Tetrahedron Letters, 56:33 (2015), 4804
Boris A. Trofimov, Ludmila V. Andriyankova, Kseniya V. Belyaeva, Lina P. Nikitina, Andrei V. Afonin, Anastasiya G. Mal'kina, “Ring‐Opening of Pyridines with Acylacetylenes and Water: Straightforward Access to 5‐[(Z)‐Acylethenyl]amino‐2,4‐pentadienals”, Eur J Org Chem, 2015:36 (2015), 7876
K. V. Belyaeva, A. V. Afonin, L. V. Andriyankova, O. G. Volostnykh, L. P. Nikitina, A. G. Mal'kina, I. A. Ushakov, V. I. Smirnov, L. V. Klyba, B. A. Trofimov, “2,4-Diphenylpyrido[2,1-a]isoquinolinium nitrite from the domino reaction between isoquinoline, 1,3-diphenylprop-2-yn-1-one and nitromethane”, Mendeleev Commun., 24:3 (2014), 156–158
N. M. Slyn'ko, L. E. Tatarova, M. M. Shakirov, E. E. Shul'ts, “Synthesis of N-aryloxyalkylanabasine derivatives”, Chem Nat Compd, 49:2 (2013), 294
B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, “New methodology for functionalization of the imidazole ring by alkynes”, Chem Heterocycl Comp, 48:1 (2012), 147
Boris A. Trofimov, Anastasiya G. Mal'kina, Valentina V. Nosyreva, Olesya A. Shemyakina, Alexander I. Albanov, Andrei V. Afonin, Olga N. Kazheva, Grigorii G. Alexandrov, Oleg A. Dyachenko, “Tandem regio- and stereospecific cyclization of ethyl isonicotinate with cyanoacetylenic alcohols to provide novel polycondensed heterocyclic systems”, Tetrahedron Letters, 53:8 (2012), 927
Boris A. Trofimov, Valentina V. Nosyreva, Olesya A. Shemyakina, Anastasiya G. Mal'kina, Alexander I. Albanov, “Сhemo- and regioselective modification of adenosine with tertiary cyanopropargylic alcohols”, Tetrahedron Letters, 53:43 (2012), 5769
L. V. Andriyankova, K. V. Belyaeva, L. P. Nikitina, A. G. Mal'kina, T. I. Vakul'skaya, S. S. Khutsishvili, L. M. Sinegovskaya, B. A. Trofimov, “Signs of formation and chemical evolution of zwitterions in the reaction of 1-methylimidazole with cyanophenylacetylene and benzaldehyde”, Chem Heterocycl Comp, 47:11 (2012), 1390
Boris A. Trofimov, Ludmila V. Andriyankova, Kseniya V. Belyaeva, Anastasiya G. Mal'kina, Lina P. Nikitina, Oleg A. Dyachenko, Olga N. Kazheva, Grigorii G. Alexandrov, Gennadii V. Shilov, Andrei V. Afonin, Igor' A. Ushakov, “C(2)-Functionalization of 1-substituted imidazoles with cyanoacetylenes and aromatic or heteroaromatic aldehydes”, Tetrahedron, 67:6 (2011), 1288
Nicola Kielland, Rodolfo Lavilla, Topics in Heterocyclic Chemistry, 25, Synthesis of Heterocycles via Multicomponent Reactions II, 2010, 127
Donghui Wei, Mingsheng Tang, “DFT Study on the Mechanisms of Stereoselective C(2)-Vinylation of 1-Substituted Imidazoles with 3-Phenyl-2-propynenitrile”, J. Phys. Chem. A, 113:41 (2009), 11035
B. A. Trofimov, L. V. Andriyankova, K. V. Belyaeva, A. G. Mal'kina, L. P. Nikitina, A. V. Afonin, I. A. Ushakov, “(Z)-1-Organyl-2-(2,4-dicyano-1,3-diphenyl-1,3-butadienyl)imidazoles from 1-substituted imidazoles with phenylcyanoacetylene”, Mendeleev Commun., 19:1 (2009), 42–44
N. A. Nedolya, “Chemistry of heterocyclic compounds at the A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, over 50 years (Review)”, Chem Heterocycl Comp, 44:10 (2008), 1165
Boris A. Trofimov, Lyudmila V. Andriyankova, Kseniya V. Belyaeva, Anastasiya G. Mal'kina, Lina P. Nikitina, Andrei V. Afonin, Igor A. Ushakov, “Stereoselective C(2)-Vinylation of 1-Substituted Imidazoles with 3-Phenyl-2-propynenitrile”, J. Org. Chem., 73:22 (2008), 9155
M. G. Voronkov, “Academician Boris Aleksandrovich Trofimov”, Chem Heterocycl Comp, 44:9 (2008), 1029
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