Abstract:
The reaction of 3-nitro-2-trichloromethyl-2H-chromenes with hydrazine hydrate in ethanol at room temperature results in 3,4-trans, 4,5-trans-3-(2-hydroxyaryl)-4-nitro-5-trichloromethylpyrazolidines in 56–73% yields; the structures of these compounds were established by 1H NMR, 2D COSY and 2D NOESY spectra.
Document Type:
Article
Language: English
Citation:
V. Yu. Korotaev, I. B. Kutyashev, V. Ya. Sosnovskikh, M. I. Kodess, “Stereoselective synthesis of N-unsubstituted pyrazolidines from 3-nitro-2-trichloromethyl-2H-chromenes and hydrazine hydrate”, Mendeleev Commun., 17:1 (2007), 52–53
Linking options:
https://www.mathnet.ru/eng/mendc3375
https://www.mathnet.ru/eng/mendc/v17/i1/p52
This publication is cited in the following 16 articles:
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Lennart Lykke, Bjørn Dreiø Carlsen, Raoní Scheibler Rambo, Karl Anker Jørgensen, “Catalytic Asymmetric Synthesis of 4-Nitropyrazolidines: An Access to Optically Active 1,2,3-Triamines”, J. Am. Chem. Soc., 136:32 (2014), 11296
Azim Ziyaei Halimehjani, Irishi N. N. Namboothiri, Seyyed Emad Hooshmand, “Part I: Nitroalkenes in the synthesis of heterocyclic compounds”, RSC Adv., 4:89 (2014), 48022
Vladislav Yu. Korotaev, Alexey Yu. Barkov, Vladimir S. Moshkin, Evgeniya G. Matochkina, Mikhail I. Kodess, Vyacheslav Ya. Sosnovskikh, “Highly diastereoselective 1,3-dipolar cycloaddition of nonstabilized azomethine ylides to 3-nitro-2-trihalomethyl-2H-chromenes: synthesis of 1-benzopyrano[3,4-c]pyrrolidines”, Tetrahedron, 69:40 (2013), 8602
Vladislav Yu. Korotaev, Alexey Yu. Barkov, Vyacheslav Ya. Sosnovskikh, “Synthesis of 5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridines from 3-nitro-2-(trifluoromethyl)-2H-chromenes and aminoenones derived from acetylacetone and cyclic amines”, Tetrahedron Letters, 54:24 (2013), 3091
V. Yu. Korotaev, V. Ya. Sosnovskikh, A. Yu. Barkov, “Synthesis and properties of 3-nitro-2H-chromenes”, Russian Chem. Reviews, 82:12 (2013), 1081–1116
V. Yu. Korotaev, A. Yu. Barkov, A. A. Sokovnina, V. Ya. Sosnovskikh, “Highly Regio-and Stereoselective Addition of Ethyl 3-Aminobut-2-enoates to 2-substituted 3-nitro-2H-chromenes”, Mendeleev Commun., 23:3 (2013), 150–152
Vladislav Yu. Korotaev, Vyacheslav Ya. Sosnovskikh, Alexey Yu. Barkov, Pavel A. Slepukhin, Marina A. Ezhikova, Mikhail I. Kodess, Yurii V. Shklyaev, “A simple synthesis of the pentacyclic lamellarin skeleton from 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1-methyl(benzyl)-3,4-dihydroisoquinolines”, Tetrahedron, 67:45 (2011), 8685
Vladislav Yu. Korotaev, Vyacheslav Ya. Sosnovskikh, Mikhail A. Barabanov, Evgeniya S. Yasnova, Marina A. Ezhikova, Mikhail I. Kodess, Pavel A. Slepukhin, “Stereoselective hetero-Diels–Alder reaction of 3-nitro-2-trihalomethyl-2H-chromenes with 2,3-dihydrofuran and ethyl vinyl ether under solvent-free conditions”, Tetrahedron, 66:6 (2010), 1404
V. Yu. Korotaev, V. Ya. Sosnovskikh, E. S. Yasnova, A. Yu. Barkov, Yu. V. Shklyaev, “A simple synthesis of the lamellarin analogues from 3-nitro-2-trifluoromethyl-2H-chromenes and 1-benzyl-3,4-dihydroisoquinolines”, Mendeleev Commun., 20:6 (2010), 321–322
Pateliya Mujjamil Habib, Veerababurao Kavala, B. Rama Raju, Chun‐Wei Kuo, Wen‐Chang Huang, Ching‐Fa Yao, ““On‐Water”‐Promoted C‐Alkylation of Indoles with 2‐Aryl‐3‐nitro‐2H‐chromenes under Catalyst‐Free Conditions”, Eur J Org Chem, 2009:26 (2009), 4503
Vladislav Yu. Korotaev, Vyacheslav Ya. Sosnovskikh, Igor B. Kutyashev, Alexey Yu. Barkov, Yurii V. Shklyaev, “A facile route to the pentacyclic lamellarin skeleton via Grob reaction between 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1,3,3-trimethyl-3,4-dihydroisoquinolines”, Tetrahedron Letters, 49:37 (2008), 5376
Vladislav Yu. Korotaev, Vyacheslav Ya. Sosnovskikh, Igor B. Kutyashev, Alexey Yu. Barkov, Evgeniya G. Matochkina, Mikhail I. Kodess, “A simple and convenient synthesis of 4-methyl-3-nitro-2-trihalomethyl-2H-chromenes from N-unsubstituted imines of 2-hydroxyacetophenones and trichloro(trifluoro)ethylidene nitromethanes”, Tetrahedron, 64:22 (2008), 5055
V. Yu. Korotaev, V. Ya. Sosnovskikh, I. B. Kutyashev, “Reactions of 3-nitro-2-trihalomethyl-2H-chromenes with indole, N-methylindole, and N-methylpyrrole. Stereoselective synthesis of 4-azolyl-3-nitro-2-trihalomethylchromanes”, Russ Chem Bull, 56:10 (2007), 2054
Vladislav Yu. Korotaev, Igor B. Kutyashev, Vyacheslav Ya. Sosnovskikh, Mikhail I. Kodess, “Stereoselective Synthesis of N‐Unsubstituted Pyrazolidines from 3‐Nitro‐2‐trichloromethyl‐2H‐chromenes and Hydrazine Hydrate.”, ChemInform, 38:34 (2007)
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