Abstract:
Treatment of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’ (3’H)-one with POCl3 and DMF gives a mixture of 1,2,3,4,5,6,7,8-octahydroacridine-4-carbonitrile and 4,5-diformyl-2,3,6,7,8,10-hexahydroacridine-8a(1H)-carbonitrile, both products resulting from cascade transformations of the primary Vilsmeier intermediates.
Citation:
V. I. Markov, O. K. Farat, S. A. Varenichenko, E. V. Velikaya, “Rearrangement of 5’,6’,7’,8’-tetrahydro-1’H-spiro(cyclohexane-1,2’-quinazolin)-4’(3’H)-one during the Vilsmeier reaction”, Mendeleev Commun., 22:2 (2012), 101–102
Linking options:
https://www.mathnet.ru/eng/mendc2754
https://www.mathnet.ru/eng/mendc/v22/i2/p101
This publication is cited in the following 18 articles:
N.V. Smetanin, S.A. Varenichenko, A.V. Kharchenko, O.K. Farat, V.I. Markov, “Synthesis of new substituted pyridines via Vilsmeier-Haack reagent”, Vopr. Khim. Khim. Tekhnol., 2023, no. 1, 34
S.A. Varenichenko, A.V. Kharchenko, O.K. Farat, “Synthesis and in silico ADMET profiling of novel 5-arylidene-2-(2,3,5,6,7,8-hexahydroacridin-4(1H)-ylidene)-1,3-thiazolidin-4-ones”, Vopr. Khim. Khim. Tekhnol., 2023, no. 6, 37
O.K. Farat, S.A. Varenichenko, E.V. Zaliznaya, V.I. Markov, “Novel examples of electrophilic rearrangement of substituted pyrimidin-4-ones under Vilsmeier-Haack reaction condition”, Vopr. Khim. Khim. Tekhnol., 2022, no. 3, 92
Oleg K. Farat, Anton V. Kovtun, Svetlana A. Varenichenko, Iryna V. Hovor, Yuliia V. Skrypynets, Darya I. Aleksandrova, Inna I. Leonenko, Alla V. Yegorova, Aleksander V. Mazepa, Victor I. Markov, “Novel xanthene-like dyes: synthesis and spectral properties”, Monatsh Chem, 153:5-6 (2022), 443
Oleg K. Farat, Anton V. Kovtun, Svetlana A. Varenichenko, Aleksander V. Mazepa, Victor I. Markov, “Novel rearrangement of 1,3-benzo(naphtho)dioxin-4(1)-ones under Vilsmeier-Haack reagent”, Monatsh Chem, 152:1 (2021), 95
Nikolay Smetanin, Sofia Tokarieva, Svetlana Varenichenko, Oleg Farat, Victor Markov, “IN SILICO PREDICTION AND MOLECULAR DOCKING STUDIES OF BIOLOGICAL ACTIVITY OF HYDROACRIDINE (QUINOLINE) DERIVATIVES”, Ukr. Chem. Journ., 87:5 (2021), 38
Oleg K. Farat, Nikolai V. Smetanin, Svetlana A. Varenichenko, Mariia B. Kaidash, Ekaterina V. Zaliznaya, Victor I. Markov, “Novel rearrangement of substituted spiroimidazolidinones into quinoline derivatives via Vilsmeier-Haack reagent”, Tetrahedron Letters, 85 (2021), 153464
O.K. Farat, E.V. Zaliznaya, S.A. Varenichenko, V.I. Markov, “Rearrangement of substituted pyrimidin-4-ones under the Vilsmeier-Haack reaction”, Vopr. Khim. Khim. Tekhnol., 2021, no. 1, 101
A. V. Kovtun, S. V. Tokarieva, S. A. Varenichenko, O. K. Farat, A. V. Mazepa, V. V. Dotsenko, V. I. Markov, “Spirocyclic thienopyrimidines: synthesis, new rearrangements under Vilsmeier conditions and in silico prediction of anticancer activity”, Biopolym. Cell, 36:4 (2020), 279
O.K. Farat, E.V. Zaliznaya, S.A. Varenichenko, V.I. Markov, “Synthesis of tetrahydroacridine derivatives through the Vilsmeier-Haack reaction”, VKhKhT, 2020, no. 1, 92
“Synthesis of new Schiff bases based on formyl derivatives of xanthenes”, VKhKhT, 2019, no. 5, 22
Oleg K. Farat, Ivan V. Ananyev, Svetlana A. Varenichenko, Ekaterina V. Zaliznaya, Victor I. Markov, “A facile approach for the synthesis of novel xanthene derivatives with Vilsmeier–Haack reagent”, Chem Heterocycl Comp, 55:1 (2019), 38
Oleg K. Farat, Ivan V. Ananyev, Svetlana A. Varenichenko, Anatoliy L. Tatarets, Victor I. Markov, “Vilsmeier-Haack reagent: An efficient reagent for the transformation of substituted 1,3-naphthoxazines into xanthene-type dyes”, Tetrahedron, 75:19 (2019), 2832
Ekaterina V. Zaliznaya, Oleg K. Farat, Svetlana A. Varenichenko, Alexander V. Mazepa, Victor I. Markov, “Functionalization of tetra- and octahydroacridine derivatives through Michael addition”, Tetrahedron Letters, 57:31 (2016), 3485
Oleg K. Farat, Victor I. Markov, Svetlana A. Varenichenko, Victor V. Dotsenko, Alexander V. Mazepa, “The Vilsmeier–Haack formylation of 2,3-dihydro-4H-1,3-benzoxazin-4-ones and isomeric 1,2-dihydro-4H-3,1-benzoxazin-4-ones: an effective approach to functionalized 2H-/4H-chromenes and tetrahydroacridines”, Tetrahedron, 71:34 (2015), 5554
Ekaterina V. Zaliznaya, Oleg K. Farat, Nikolay Yu. Gorobets, Viktor I. Markov, Roman I. Zubatyuk, Aleksandr V. Mazepa, Elena V. Vashchenko, “Reactions of octahydroacridine-4-carbonitrile (carboxamide) with electrophilic reagents”, Chem Heterocycl Comp, 51:4 (2015), 327
S. A. Varenichenko, O. K. Farat, V. I. Markov, “Reactivity of Substituted 2-Spiropyrimidin-4-Ones Under Vilsmeier–Haack Conditions”, Chem Heterocycl Comp, 50:11 (2015), 1602
V. I. Markov, O. K. Farat, S. A. Varenichenko, E. V. Velikaya, R. I. Zubatyuk, O. V. Shishkin, “Synthesis and Formylation of Substituted 2-Spiropyrimidin-4-ones and Related Compounds”, Chem Heterocycl Comp, 49:8 (2013), 1158
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