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

Vasilissa V. Shirokova; Viktoria A. Ikonnikova; Pavel N. Solyev; Vladislav A. Lushpa; Alexander A. Korlyukov; Alexander D. Volodin; Nadezhda S. Baleeva; Mikhail S. Baranov; Andrey A. Mikhaylov

doi:10.1055/a-1559-2728

Synthesis, Inhaltsverzeichnis

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

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation

^bHigher Chemical College, D.I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya sq., 125047 Moscow, Russian Federation

,

Viktoria A. Ikonnikova

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation

^bHigher Chemical College, D.I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya sq., 125047 Moscow, Russian Federation

,

Pavel N. Solyev

^cEngelhardt Institute of Molecular Biology of the Russian Academy of Sciences, 32 Vavilova St., Moscow, 119991, Russian Federation

,

Vladislav A. Lushpa

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation

,

Alexander A. Korlyukov

^dNesmeyanov Institute of Organoelement Compounds, 28 Vavilov St., Moscow, 119334, Russian Federation

,

Alexander D. Volodin

^dNesmeyanov Institute of Organoelement Compounds, 28 Vavilov St., Moscow, 119334, Russian Federation

,

Nadezhda S. Baleeva

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation

,

Mikhail S. Baranov

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation

,

Andrey A. Mikhaylov ∗

^aShemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russian Federation

^eNational Research University Higher School of Economics, 20 Myasnitskaya St., Moscow, 101000, Russian Federation

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Abstract

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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

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Referenzen

References
1 Varejao JO. S, Varejao EV. V, Fernandes SA. Eur. J. Org. Chem. 2019; 4273
2 Hendrickx E, Van Steenwinckel D, Persoons A, Samyn C, Beljonne D, Brédas JL. J. Chem. Phys. 2000; 113: 5439
3 Moylan CR. J. Phys. Chem. 1994; 98: 13513
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
7 Wang C, Han ZY, Luo HW, Gong LZ. Org. Lett. 2010; 12: 2266
8 Katritzky AR, Rachwal B, Rachwal S, Abboud K. J. Org. Chem. 1996; 61: 3117
9 An X.-D, Xiao J. Org. Chem. Front. 2021; 8: 1364
10 Xiao M, Zhu S, Shen Y, Wang L, Xiao J. Chin. J. Org. Chem. 2018; 38: 328
11 Wang L, Xiao J. Adv. Synth. Catal. 2014; 356: 1137
12 Haibach MC, Seidel D. Angew. Chem. Int. Ed. 2014; 53: 5010
13 Wang L, Xiao J. Top. Curr. Chem. 2016; 374: 17
14 Peng B, Maulide N. Chem. Eur. J. 2013; 19: 13274
15 Murarka S, Zhang C, Konieczynska MD, Seidel D. Org. Lett. 2009; 11: 129
16 Murarka S, Deb I, Zhang C, Seidel D. J. Am. Chem. Soc. 2009; 131: 13226
17 Duan K, An X.-D, Li LF, Sun LL, Qiu B, Li XJ, Xiao J. Org. Lett. 2020; 22: 2537
18 Anderson JC, Chang CH, Corpinot MK, Nunn M, Ware OJ. Tetrahedron 2019; 75: 130663
19 Bhowmik A, Das S, Sarkar W, Saidalavi KM, Mishra A, Roy A, Deb I. Adv. Synth. Catal. 2021; 363: 826
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
21 Li SS, Lv X, Ren D, Shao CL, Liu Q, Xiao J. Chem. Sci. 2018; 9: 8253
22 Li SS, Zhou L, Wang L, Zhao H, Yu L, Xiao J. Org. Lett. 2018; 20: 138
23 Wang S, An X.-D, Li SS, Liu X, Liu Q, Xiao J. Chem. Commun. 2018; 54: 13833
24 Li SS, Zhu S, Chen C, Duan K, Liu Q, Xiao J. Org. Lett. 2019; 21: 1058
25 Wang S, Shen Y.-B, Li L.-F, Qiu B, Yu L, Liu Q, Xiao J. Org. Lett. 2019; 21: 8904
26 Alajarin M, Marin-Luna M, Vidala A. Adv. Synth. Catal. 2011; 353: 557
27 McQuaid KM, Sames D. J. Am. Chem. Soc. 2009; 131: 402
28 McQuaid KM, Long JZ, Sames D. Org. Lett. 2009; 11: 2972
29 Otawa Y, Mori K. Chem. Commun. 2019; 55: 13856
30 Kataoka M, Otawa Y, Ido N, Mori K. Org. Lett. 2019; 21: 9334
31 Manahelohe GM, Potapov AY, Shikhaliev KS. Russ. Chem. Bull. 2016; 65: 1145
32 Sugasawa T, Hamana H, Toyoda T, Adachi M. Synthesis 1979; 99
33 Molander GA, Romero JA. C. Tetrahedron 2005; 61: 2631
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
36 Peterson JP, Ellern A, Winter AH. J. Am. Chem. Soc. 2020; 142: 5304
37 Wang H, Huang Y, Jiang Q, Dai X, Shi F. Chem. Commun. 2019; 55: 3915

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