Abstract:
Ethyl 3-aminobut-2-enoates MeC(NHR)=CHCO2Et (R = H, Me, Bn) whose reaction site is C(2) atom add to 2-R-3-nitro-2H-chromenes at their C(4) atom to give the corresponding trans,trans-2,3,4-trisubstituted chromanes. Analogous substrates MeC(NR2)=CHCO2Et (NR2 is piperidin-1-yl or morpholin-4-yl) react by their C(4) methyl group to afford cis,trans-2,3,4-trisubstituted chromanes. The stereochemistry of the products was established by X-ray diffraction analysis.
Citation:
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
Linking options:
https://www.mathnet.ru/eng/mendc2644
https://www.mathnet.ru/eng/mendc/v23/i3/p150
This publication is cited in the following 9 articles:
Tapaswini Das, Seetaram Mohapatra, Asit Kumar Pradhan, Sabita Nayak, “Recent Advances of Michael/hetero‐Michael Addition Reaction in the Synthesis of 3‐Nitro‐2H‐chromene Derivatives”, ChemistrySelect, 8:14 (2023)
Vladislav Yu. Korotaev, Igor B. Kutyashev, Alexey Yu. Barkov, Vyacheslav Ya. Sosnovskikh, “Stereoselective addition of ethyl 3-morpholino(piperidino)-crotonates to 2-trihalomethyl-3-nitro-2H-chromenes. Synthesis of 4-acetonyl-3-nitrochromans”, Chem Heterocycl Comp, 51:5 (2015), 440
Vladislav Yu. Korotaev, Alexey Yu. Barkov, Igor B. Kutyashev, Ivan V. Kotovich, Marina A. Ezhikova, Mikhail I. Kodess, Vyacheslav Ya. Sosnovskikh, “Highly regio- and stereoselective addition of aminoenones to 2-substituted 3-nitro-2H-chromenes. Unexpected synthesis of 5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridines”, Tetrahedron, 71:18 (2015), 2658
Vladislav Yu. Korotaev, Alexey Yu. Barkov, Marina A. Ezhikova, Mikhail I. Kodess, Vyacheslav Ya. Sosnovskikh, “Synthesis of trans,trans-2,3,4-trisubstituted chromans from 3-nitro-2N-chromenes and enamines of acetoacetic ester and acetylacetone. A new type of configurationally stable atropisomers”, Chem Heterocycl Comp, 51:6 (2015), 531
Yuanyuan Zhu, Xiaoyuan Li, Qiao Chen, Jinhuan Su, Fengjing Jia, Shuai Qiu, Mingxia Ma, Quantao Sun, Wenjin Yan, Kairong Wang, Rui Wang, “Highly Enantioselective Cascade Reaction Catalyzed by Squaramides: the Synthesis of CF3-Containing Chromanes”, Org. Lett., 17:15 (2015), 3826
Na Wu, Benoit Wahl, Simon Woodward, William Lewis, “1,4‐Addition of TMSCCl3 to Nitroalkenes: Efficient Reaction Conditions and Mechanistic Understanding”, Chemistry A European J, 20:25 (2014), 7718
Vladislav Yu. Korotaev, Alexey Yu. Barkov, Anna A. Sokovnina, Vyacheslav Ya. Sosnovskikh, “ChemInform Abstract: Highly Regio‐ and Stereoselective Addition of Ethyl 3‐Aminobut‐2‐enoates to 2‐Substituted 3‐Nitro‐2H‐chromenes.”, ChemInform, 44:44 (2013)
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
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