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CATALYTIC AND DIASTEREOSELECTIVE CASCADE REACTION FOR THE PREPARATION OF cis-1,3-DISUBSTITUTED ISOINDOLINE-AMINAL HYBRID COMPOUNDS
About TSUJIHARA Tetsuya
About Iwate Medical Univ., Iwate, JPN
About SUZUKI Takeyuki
About Osaka Univ., Osaka, JPN
About KAWANO Tomikazu
About Iwate Medical Univ., Iwate, JPN
Material：
About Heterocycles
Volume： 102 Issue： 4 Page： 723-730 Publication year： Apr. 01, 2021
JST Material Number： S0966A ISSN： 0385-5414 CODEN： HTCYAM Document type： Article
Article type： 短報 Country of issue： Japan (JPN) Language： ENGLISH (EN)
Keywords indexed to the article.
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About asymmetric synthesis
About consecutive reaction
About base catalytic reaction
About diamine
About Michael reaction
About cyclization reaction
About nitrogen heterocyclic compound
About polynuclear aromatic compound
About stereoselectivity
About diastereomer
About Aza-Michael Reaction
About aminal
About isoindoline derivatives
About cascade reaction
About diastereoselectivity
About aromatic amine
About primary amine
Category name(code) classified by JST.
About Catalytic reactions in general
About Condensed derivatives of pyrroles
Chemical Substance indexed to the Article.
About (E)-2-(Tosyliminomethyl)-cinnamic acid methyl ester
About 1-Methyl-1,3:2,3-dipropanoguanidine
About 4-Methoxyaniline
About p-Toluidine
About rel-2-[(1R*,3R*)-3-(4-メチルフェニルアミノ)-2-トシルイソインドリン-1-イル]酢酸メチル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-(4-クロロフェニルスルホニル)イソインドリン-1-イル]酢酸メチル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-(4-メトキシフェニルスルホニル)イソインドリン-1-イル]酢酸メチル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-(フェニルスルホニル)イソインドリン-1-イル]酢酸メチル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-トシルイソインドリン-1-イル]アセトニトリル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-トシルイソインドリン-1-イル]酢酸tert-ブチル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-トシルイソインドリン-1-イル]酢酸エチル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-トシルイソインドリン-1-イル]酢酸メチル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-トシルイソインドリン-1-イル]酢酸ベンジル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-トシル-4-メトキシイソインドリン-1-イル]酢酸メチル
About rel-2-[(1R*,3R*)-3-(4-メトキシフェニルアミノ)-2-トシル-5-クロロイソインドリン-1-イル]酢酸メチル
- For relevant reviews: (a) L. F. Tietze and U. Beifuss, Angew. Chem., Int. Ed. Engl., 1993, 32, 131; (b) L. F. Tietze, Chem. Rev., 1996, 96, 115; (c) H. Pellissier, Adv. Synth. Catal., 2012, 354, 237; (d) C. M. R. Volla, I. Atodiresei, and M. Rueping, Chem. Rev., 2014, 114, 2390; (e) F. Vetica, R. M. de Figueiredo, M. Orsini, D. Tofani, and T. Gasperi, Synthesis, 2015, 47, 2139; (f) H. Pellissier, Synthesis, 2020, 52, 3837; (g) N. Losada-Garcia, Z. Cabrera, P. Urrutia, C. Garcia-Sanz, A. Andreu, and J. M. Palomo, Catalysts, 2020, 10, 1258; (h) S. Takizawa, Chem. Pharm. Bull., 2020, 68, 299.
- Synthesis of 1,3-disubstituted isoindolines by cascade or domino process: (a) D. Enders, A. A. Narine, F. Toulgoat, and T. Bisschops, Angew. Chem. Int. Ed., 2008, 47, 5661; (b) S. Fustero, J. Moscardó, M. Sánchez-Roselló, E. Rodríguez, and P. Barrio, Org. Lett., 2010, 12, 5494; (c) B. Qian, S. Guo, C. Xia, and H. Huang, Adv. Synth. Catal., 2010, 352, 3195; (d) S. Takizawa, N. Inoue, S. Hirata, and H. Sasai, Angew. Chem. Int. Ed., 2010, 49, 9725; (e) E. E. Maciver, P. C. Knipe, A. P. Cridland, A. L. Thompson, and M. D. Smith, Chem. Sci., 2012, 3, 537; (f) S. Takizawa, M. Sako, M. A. Abozeid, K. Kishi, H. D. P. Wathsala, S. Hirata, K. Murai, H. Fujioka, and H. Sasai, Org. Lett., 2017, 19, 5426; (g) B. G. Das, S. Shah, and V. K. Singh, Org. Lett., 2019, 21, 4981; (h) Z.-R. Guan, Q. Wan, and M.-W. Ding, Tetrahedron, 2019, 75, 4626; (i) K. Hirano, T. Saito, Y. Fujihira, D. M. Sedgwick, S. Fustero, and N. Shibata, J. Org. Chem., 2020, 85, 7976.
- Selected recent reports on the synthesis of 1,3-disubstituted isoindolines: (a) S. Xing, J. Ren, K. Wang, H. Cui, H. Yan, and W. Li, Adv. Synth. Catal., 2016, 358, 532; (b) R. Achary, I.-A. Jung, S.-M. Son, and H.-K. Lee, J. Org. Chem., 2017, 82, 7223; (c) R. Achary, I.-A. Jung, and H.-K. Lee, J. Org. Chem., 2018, 83, 3864; (d) Y. Tao and S. R. Gilbertson, Chem. Commun., 2018, 54, 11292; (e) S. Xing, H. Cui, J. Qin, N. Gu, B. Zhang, K. Wang, Y. Wang, L. Xia, and Y. Wang, Org. Chem. Front., 2018, 5, 1950; (f) Z. Feng, Z. Yuan, X. Zhao, Y. Huang, and H. Yao, Org. Chem. Front., 2019, 6, 3535 and references cited therein.
- Selected review and reports: (a) K. Speck and T. Magauer, Beilstein J. Org. Chem., 2013, 9, 2048; (b) M. S. Leonard, ARKIVOC, 2013, i, 1; (c) J. L. Moniot, D. M. Hindenlang, and M. Shamma, J. Org. Chem., 1979, 44, 4347; (d) M. Goldstein, S. Kuga, N. Kusano, E. Meller, J. Dancis, and R. Schwarcz, Brain Res., 1986, 367, 114; (e) A. L. Jaton, R. K. A. Giger, J. M. Vigouret, A. Enz, W. Frick, A. Closse, and R. Markstein, Life Sci., 1986, 38, 155; (f) Z. Hussein, D. J. Mulford, B. A. Bopp, and G. R. Granneman, Br. J. Clin. Pharmacol., 1993, 36, 357; (g) T. Kondo, K. Yoshida, and S. Tanayama, Arzneimittelforschung, 1996, 46, 839; (h) P. J. Kukkola, N. A. Bilci, T. Ikler, P. Savage, S. S. Shetty, D. DelGrande, and A. Y. Jeng, Bioorg. Med. Chem. Lett., 2001, 11, 1737; (i) T. L. Stuk, B. K. Assink, R. C. Bates, D. T. Erdman, V. Fedij, S. M. Jennings, J. A. Lassig, R. J. Smith, and T. L. Smith, Org. Process Res. Dev., 2003, 7, 851.
- T, Tsujihara, H. Yamauchi, S. Tamura, T. Takehara, T. Suzuki, and T. Kawano, Tetrahedron Lett., 2020, 61, 152122.
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