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Synthesis 2021; 53(24): 4689-4699
DOI: 10.1055/a-1559-2728
paper

1,5-Hydride-Shift-Triggered Cyclization for the Synthesis of Unsymmetric Julolidines

Vasilissa V. Shirokova
a   Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation
b   Higher Chemical College, D.I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya sq., 125047 Moscow, Russian Federation
,
Viktoria A. Ikonnikova
a   Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation
b   Higher Chemical College, D.I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya sq., 125047 Moscow, Russian Federation
,
Pavel N. Solyev
c   Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences, 32 Vavilova St., Moscow, 119991, Russian Federation
,
Vladislav A. Lushpa
a   Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation
,
Alexander A. Korlyukov
d   Nesmeyanov Institute of Organoelement Compounds, 28 Vavilov St., Moscow, 119334, Russian Federation
,
Alexander D. Volodin
d   Nesmeyanov Institute of Organoelement Compounds, 28 Vavilov St., Moscow, 119334, Russian Federation
,
Nadezhda S. Baleeva
a   Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation
,
Mikhail S. Baranov 
a   Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation
,
Andrey A. Mikhaylov  ∗
a   Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation
e   National Research University Higher School of Economics, 20 Myasnitskaya St., Moscow, 101000, Russian Federation
› Author AffiliationsThe authors gratefully acknowledge support from the Russian Science Foundation (Grant No. 20-73-10195).
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Abstract

Directly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride-shift-triggered cyclization to provide difficult to access julolidine derivatives in yields of 21–98% under scandium(III) triflate catalysis. Additionally, the scope of the reaction, several follow-up transformations and a remarkable side process discovered during optimization of the conditions are highlighted.

Key words

julolidine - 1,5-hydride shift - redox-neutral reaction - tetrahydroquinoline - catalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1559-2728.
  • Supporting Information


Publication History

Received: 31 May 2021

Accepted after revision: 27 July 2021

Accepted Manuscript online:
27 July 2021

Article published online:
30 August 2021

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  • References

  • 1 Varejao JO. S, Varejao EV. V, Fernandes SA. Eur. J. Org. Chem. 2019; 4273
    Crossref
  • 2 Hendrickx E, Van Steenwinckel D, Persoons A, Samyn C, Beljonne D, Brédas JL. J. Chem. Phys. 2000; 113: 5439
    Crossref
  • 3 Moylan CR. J. Phys. Chem. 1994; 98: 13513
    Crossref
  • 4 Ito F, Koike H, Morita A. US 6869960B2, 2005
  • 5 Fevig JM, Mitchell IS, Lee T, Chen W, Cacciola J. WO 02/059124A2, 2002
  • 6 Rao Lingam VS. P, Thomas A, Mukkanti K, Gopalan B. Synth. Commun. 2011; 41: 1809
    Crossref
  • 7 Wang C, Han ZY, Luo HW, Gong LZ. Org. Lett. 2010; 12: 2266
    CrossrefPubMed
  • 8 Katritzky AR, Rachwal B, Rachwal S, Abboud K. J. Org. Chem. 1996; 61: 3117
    CrossrefPubMed
  • 9 An X.-D, Xiao J. Org. Chem. Front. 2021; 8: 1364
    Crossref
  • 10 Xiao M, Zhu S, Shen Y, Wang L, Xiao J. Chin. J. Org. Chem. 2018; 38: 328
    Crossref
  • 11 Wang L, Xiao J. Adv. Synth. Catal. 2014; 356: 1137
    Crossref
  • 12 Haibach MC, Seidel D. Angew. Chem. Int. Ed. 2014; 53: 5010
    CrossrefPubMed
  • 13 Wang L, Xiao J. Top. Curr. Chem. 2016; 374: 17
    CrossrefPubMed
  • 14 Peng B, Maulide N. Chem. Eur. J. 2013; 19: 13274
    CrossrefPubMed
  • 15 Murarka S, Zhang C, Konieczynska MD, Seidel D. Org. Lett. 2009; 11: 129
    CrossrefPubMed
  • 16 Murarka S, Deb I, Zhang C, Seidel D. J. Am. Chem. Soc. 2009; 131: 13226
    CrossrefPubMed
  • 17 Duan K, An X.-D, Li LF, Sun LL, Qiu B, Li XJ, Xiao J. Org. Lett. 2020; 22: 2537
    CrossrefPubMed
  • 18 Anderson JC, Chang CH, Corpinot MK, Nunn M, Ware OJ. Tetrahedron 2019; 75: 130663
    Crossref
  • 19 Bhowmik A, Das S, Sarkar W, Saidalavi KM, Mishra A, Roy A, Deb I. Adv. Synth. Catal. 2021; 363: 826
    Crossref
  • 20 Zaitseva ER, Smirnov AYu, Myasnyanko IN, Mineev KS, Sokolov AI, Volkhina TN, Mikhaylov AA, Baleeva NS, Baranov MS. New. J. Chem. 2021; 45: 1805
    Crossref
  • 21 Li SS, Lv X, Ren D, Shao CL, Liu Q, Xiao J. Chem. Sci. 2018; 9: 8253
    CrossrefPubMed
  • 22 Li SS, Zhou L, Wang L, Zhao H, Yu L, Xiao J. Org. Lett. 2018; 20: 138
    CrossrefPubMed
  • 23 Wang S, An X.-D, Li SS, Liu X, Liu Q, Xiao J. Chem. Commun. 2018; 54: 13833
    CrossrefPubMed
  • 24 Li SS, Zhu S, Chen C, Duan K, Liu Q, Xiao J. Org. Lett. 2019; 21: 1058
    CrossrefPubMed
  • 25 Wang S, Shen Y.-B, Li L.-F, Qiu B, Yu L, Liu Q, Xiao J. Org. Lett. 2019; 21: 8904
    CrossrefPubMed
  • 26 Alajarin M, Marin-Luna M, Vidala A. Adv. Synth. Catal. 2011; 353: 557
    Crossref
  • 27 McQuaid KM, Sames D. J. Am. Chem. Soc. 2009; 131: 402
    CrossrefPubMed
  • 28 McQuaid KM, Long JZ, Sames D. Org. Lett. 2009; 11: 2972
    CrossrefPubMed
  • 29 Otawa Y, Mori K. Chem. Commun. 2019; 55: 13856
    CrossrefPubMed
  • 30 Kataoka M, Otawa Y, Ido N, Mori K. Org. Lett. 2019; 21: 9334
    CrossrefPubMed
  • 31 Manahelohe GM, Potapov AY, Shikhaliev KS. Russ. Chem. Bull. 2016; 65: 1145
    Crossref
  • 32 Sugasawa T, Hamana H, Toyoda T, Adachi M. Synthesis 1979; 99
    Article in Thieme Connect
  • 33 Molander GA, Romero JA. C. Tetrahedron 2005; 61: 2631
    Crossref
  • 34 CCDC 2096253 (1ab) and CCDC 2096254 (1ad) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
  • 35 Krapcho AP, Jahngen EG. E, Lovey AJ, Short FW. Tetrahedron Lett. 1974; 15: 1091
    Crossref
  • 36 Peterson JP, Ellern A, Winter AH. J. Am. Chem. Soc. 2020; 142: 5304
    CrossrefPubMed
  • 37 Wang H, Huang Y, Jiang Q, Dai X, Shi F. Chem. Commun. 2019; 55: 3915
    CrossrefPubMed