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Mendeleev Communications, 2002, Volume 12, Issue 1, Pages 27–28
DOI: https://doi.org/10.1070/MC2002v012n01ABEH001545
(Mi mendc4076)
 

This article is cited in 33 scientific papers (total in 33 papers)

Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline

V. P. Krasnov, G. L. Levit, I. N. Andreeva, A. N. Grishakov, V. N. Charushin, O. N. Chupakhin

I. Ya. Postovsky Institute of Organic Synthesis, Urals Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
Abstract: The acylation of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline by (S)-naproxen acyl chloride resulted in their kinetic resolution with the predominant formation of (S,S)-diastereoisomeric amides (de 78–76%), recrystallisation of which followed by acid hydrolysis gave individual (S)-isomers of heterocyclic amines.
Document Type: Article
Language: English


Citation: V. P. Krasnov, G. L. Levit, I. N. Andreeva, A. N. Grishakov, V. N. Charushin, O. N. Chupakhin, “Kinetic resolution of (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline”, Mendeleev Commun., 12:1 (2002), 27–28
Linking options:
  • https://www.mathnet.ru/eng/mendc4076
  • https://www.mathnet.ru/eng/mendc/v12/i1/p27
  • This publication is cited in the following 33 articles:
    1. S. A. Vakarov, D. A. Gruzdev, E. N. Chulakov, G. L. Levit, V. P. Krasnov, “Kinetic resolution of racemic 3-tert-butyl-3,4-dihydro-2H-[1,4]benzoxazine via acylation with chiral acyl chlorides”, Russ Chem Bull, 68:4 (2019), 841  crossref
    2. Mohammad A. Amin, Michelle A. Camerino, Simon J. Mountford, Xiao Ma, David T. Manallack, David K. Chalmers, Martin Wills, Philip E. Thompson, “(S)-(-)-Fluorenylethylchloroformate (FLEC); preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines”, Tetrahedron, 75:43 (2019), 130591  crossref
    3. S. A. Vakarov, D. A. Gruzdev, G. L. Levit, V. P. Krasnov, V. N. Charushin, O. N. Chupakhin, “Synthesis of enantiomerically pure 2-aryloxy carboxylic acids and their derivatives”, Russian Chem. Reviews, 88:10 (2019), 1063–1080  mathnet  mathnet  crossref  isi  scopus
    4. L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, E. V. Tretyakov, V. E. Platonov, P. V. Nikul'shin, A. S. Vinogradov, Ya. V. Zonov, V. M. Karpov, T. V. Mezhenkova, A. V. Vasilyev, A. B. Koldobskii, O. S. Shilova, S. M. Morozova, Ya. V. Burgart, E. V. Shchegolkov, V. I. Saloutin, V. B. Sokolov, A. Yu. Aksinenko, V. G. Nenajdenko, M. Yu. Moskalik, V. V. Astakhova, B. A. Shainyan, A. A. Tabolin, S. L. Ioffe, V. M. Muzalevskiy, E. S. Balenkova, A. V. Shastin, A. A. Tyutyunov, V. E. Boiko, S. M. Igumnov, A. D. Dilman, N. Yu. Adonin, V. V. Bardin, S. M. Masoud, D. V. Vorobyeva, S. N. Osipov, E. V. Nosova, G. N. Lipunova, V. N. Charushin, D. O. Prima, A. G. Makarov, A. V. Zibarev, B. A. Trofimov, L. N. Sobenina, K. V. Belyaeva, V. Ya. Sosnovskikh, D. L. Obydennov, S. A. Usachev, “Organofluorine chemistry: promising growth areas and challenges”, Russian Chem. Reviews, 88:5 (2019), 425–569  mathnet  mathnet  crossref  isi  scopus
    5. Sergey A. Vakarov, Dmitry A. Gruzdev, Liliya Sh. Sadretdinova, Mikhail I. Kodess, Andrey A. Tumashov, Evgeny B. Gorbunov, Galina L. Levit, Victor P. Krasnov, “Mutual kinetic resolution of 3-methyl-3,4-dihydro-2H-1,4-benzoxazines and 2-alkoxyacyl chlorides”, Chem Heterocycl Comp, 54:4 (2018), 437  crossref
    6. Sergey A. Vakarov, Dmitry A. Gruzdev, Evgeny N. Chulakov, Liliya Sh. Sadretdinova, Andrey A. Tumashov, Marina G. Pervova, Marina A. Ezhikova, Mikhail I. Kodess, Galina L. Levit, Victor P. Krasnov, Valery N. Charushin, “Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride”, Tetrahedron: Asymmetry, 27:24 (2016), 1231  crossref
    7. E. N. Chulakov, G. L. Levit, A. A. Tumashov, N. P. Lugovskaya, N. B. Remezovskaya, A. Yu. Maksimov, V. A. Demakov, V. P. Krasnov, “Enantioselective microbial synthesis of (S)-7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine”, Russ Chem Bull, 64:5 (2015), 1097  crossref
    8. Kodai Saito, Hiromitsu Miyashita, Takahiko Akiyama, “Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines”, Chem. Commun., 51:93 (2015), 16648  crossref
    9. Sergey A. Vakarov, Dmitry A. Gruzdev, Liliya Sh. Sadretdinova, Evgeny N. Chulakov, Marina G. Pervova, Marina A. Ezhikova, Mikhail I. Kodess, Galina L. Levit, Victor P. Krasnov, “Diastereoselective acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines with 2-phenoxy carbonyl chlorides”, Tetrahedron: Asymmetry, 26:5-6 (2015), 312  crossref
    10. Dmitry A. Gruzdev, Evgeny N. Chulakov, Liliya Sh. Sadretdinova, Mikhail I. Kodess, Galina L. Levit, Victor P. Krasnov, “Synthesis of enantiomers of 3-methyl- and 3-phenyl-3,4-dihydro-2H-[1,4]benzothiazines and their 1,1-dioxides via an acylative kinetic resolution protocol”, Tetrahedron: Asymmetry, 26:4 (2015), 186  crossref
    11. S. A. Vakarov, D. A. Gruzdev, E. N. Chulakov, L. Sh. Sadretdinova, M. A. Ezhikova, M. I. Kodess, G. L. Levit, V. P. Krasnov, “Diastereoselective Acylation of Racemic Heterocyclic Amines with N-Tosyl-(S)-Prolyl Chloride and its Structural Analogs”, Chem Heterocycl Comp, 50:6 (2014), 838  crossref
    12. Valery N. Charushin, Emiliya V. Nosova, Galina N. Lipunova, Oleg N. Chupakhin, Fluorine in Heterocyclic Chemistry Volume 2, 2014, 111  crossref
    13. Dmitry A. Gruzdev, Evgeny N. Chulakov, Galina L. Levit, Marina A. Ezhikova, Mikhail I. Kodess, Victor P. Krasnov, “A comparative study on the acylative kinetic resolution of racemic fluorinated and non-fluorinated 2-methyl-1,2,3,4-tetrahydroquinolines and 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines”, Tetrahedron: Asymmetry, 24:19 (2013), 1240  crossref
    14. Victor P. Krasnov, Dmitry A. Gruzdev, Galina L. Levit, “Nonenzymatic Acylative Kinetic Resolution of Racemic Amines and Related Compounds”, Eur J Org Chem, 2012:8 (2012), 1471  crossref
    15. D. A. Gruzdev, G. L. Levit, M. I. Kodess, V. P. Krasnov, “Synthesis of enantiomers of 6-nitro- and 6-amino-2-methyl-1,2,3,4-tetrahydroquinolines”, Chem Heterocycl Comp, 48:5 (2012), 748  crossref
    16. Evgeny N. Chulakov, Dmitry A. Gruzdev, Galina L. Levit, Konstantin V. Kudryavtsev, Victor P. Krasnov, “Enantiomers of all-cis-5-(4-bromophenyl)-4-tert-butoxycarbonyl-2-methoxycarbonylpyrrolidine: preparative HPLC separation and acylative kinetic resolution of the racemate”, Tetrahedron: Asymmetry, 23:24 (2012), 1683  crossref
    17. E. N. Chulakov, G. L. Levit, A. A. Tumashov, L. Sh. Sadretdinova, V. P. Krasnov, “Kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline and its structural analogs by using 2-arylpropionyl chlorides”, Chem Heterocycl Comp, 48:5 (2012), 724  crossref
    18. Dmitry A. Gruzdev, Galina L. Levit, Victor P. Krasnov, “Acylative kinetic resolution of racemic heterocyclic amines using N-phthaloyl-(S)-amino acyl chlorides with alkyl side chains”, Tetrahedron: Asymmetry, 23:24 (2012), 1640  crossref
    19. E. N. Chulakov, D. A. Gruzdev, G. L. Levit, L. Sh. Sadretdinova, V. P. Krasnov, V. N. Charushin, “2-Arylpropionyl chlorides in kinetic resolution of racemic 3-methyl-2,3-dihydro-4H-[1,4]benzoxazines”, Russ Chem Bull, 60:5 (2011), 948  crossref
    20. Galina L. Levit, Dmitry A. Gruzdev, Victor P. Krasnov, Evgeny N. Chulakov, Liliya Sh. Sadretdinova, Marina A. Ezhikova, Mikhail I. Kodess, Valery N. Charushin, “Substituent effect on the stereoselectivity of acylation of racemic heterocyclic amines with N-phthaloyl-3-aryl-(S)-alanyl chlorides”, Tetrahedron: Asymmetry, 22:2 (2011), 185  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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