Synthesis of 4-Vinyl-1,2,3,4-tetrahydroisoquinoline from N-Tethered Benzyl-Alkenol Catalyzed by Indium(III) Chloride: Formal Synthesis of (±)-Isocyclocelabenzine

Ngangbam Renubala Devi; Sudip Shit; Bipin Kumar Behera; Anil K. Saikia

doi:10.1055/s-0037-1610750

Synthesis, Table of Contents

Synthesis 2020; 52(09): 1425-1434
DOI: 10.1055/s-0037-1610750

paper

Synthesis of 4-Vinyl-1,2,3,4-tetrahydroisoquinoline from N-Tethered Benzyl-Alkenol Catalyzed by Indium(III) Chloride: Formal Synthesis of (±)-Isocyclocelabenzine

Ngangbam Renubala Devi

,

Sudip Shit

,

Bipin Kumar Behera

,

Anil K. Saikia∗

Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India Email: asaikia@iitg.ac.in

› Author Affiliations

Abstract

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Abstract

An intramolecular Friedel–Crafts cyclization reaction catalyzed by indium(III) chloride for the formation of 4-vinyl-1,2,3,4-tetrahydroisoquinoline from N-tethered benzyl-alkenol in good yields has been described. The reaction is highly regioselective and generates an exocyclic vinyl functionality in the piperidine ring. The reaction is compatible with a wide range of functional groups. The strategy is demonstrated for the formal synthesis of (±)-isocyclocelabenzine alkaloid.

Key words

tetrahydroisoquinoline - (±)-isocyclocelabenzine - indium(III) chloride - regioselectivity - N-tethered benzyl-alkenol - Friedel–Crafts

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References

References

1a Padwa A, Danca MD. Org. Lett. 2002; 4: 715
1b Simpkins NS, Gill CD. Org. Lett. 2003; 5: 535
1c Pérard-Viret J, Souquet F, Manisse M.-L, Royer J. Tetrahedron Lett. 2010; 51: 96

2 Bruno E, Buemi MR, Luca LD, Ferro S, Monforte A.-M, Supuran CT, Vullo D, Sarro GD, Russo E, Gitto R. ChemMedChem 2016; 11: 1812
3 Wu L, Ling H, Li L, Jiang L, He M. J. Pharm. Pharmacol. 2007; 59: 695

4a Correché ER, Andujar SA, Kurdelas RR, Gómez Lechón MJ, Freile ML. R, Enriz D. Bioorg. Med. Chem. 2008; 16: 3641
4b Cech NB, Junio HA, Ackermann LW, Kavanaugh JS, Horswill AR. Planta Med. 2012; 78: 1556

5 Abe K, Saitoh T, Horiguchi Y, Uysunomiya I, Taguchi K. Biol. Pharm. Bull. 2005; 28: 1355
6 Heptner W, Schacht U. Biochem. Pharmacol. 1974; 23: 3413
7 Dhanasekaran S, Kayet A, Suneja A, Bisai V, Singh VK. Org. Lett. 2015; 17: 2780
8 Cuny GD. Tetrahedron Lett. 2004; 45: 5167
9 Name Reactions in Heterocyclic Chemistry. Li, J.-J.; John Wiley & Sons. Inc.: Hoboken; 2005: 469
10 Bandini M, Tragni M, Umani-Ronchi A. Adv. Synth. Catal. 2009; 351: 2521
11 Qurban S, Du Y, Gong J, Lina S.-X, Kang Q. Chem. Commun. 2019; 55: 8478
12 Lee SG, Kim SG. Tetrahedron 2018; 74: 3671
13 Benmekhbi L, Louafi F, Roisnel T, Hurvois J.-P. J. Org. Chem. 2016; 81: 6721
14 Chen Z, Wang Z, Sun J. Chem. Eur. J. 2013; 19: 8426

For reviews, see:

15a Galvis CE. P, Kouznetsov VV. Synthesis 2017; 49: 4535
15b Kotha S, Deodhar D, Khedkar P. Org. Biomol. Chem. 2014; 12: 9054

16 Tietze LF, Burkhardt O. Synthesis 1994; 1331
17 Zhao Z.-L, Xu Q.-L, Gu Q, Wu X.-Y, You S.-L. Org. Biomol. Chem. 2015; 13: 3086

18a Borah M, Borthakur U, Saikia AK. J. Org. Chem. 2017; 82: 1330
18b Deka MJ, Borthakur U, Saikia AK. Org. Biomol. Chem. 2016; 14: 10489
18c Ghosh P, Deka MJ, Saikia AK. Tetrahedron 2016; 72: 690
18d Borah M, Saikia AK. ChemistrySelect 2018; 3: 2162
18e Deka MJ, Indukuri K, Sultana S, Borah M, Saikia AK. J. Org. Chem. 2015; 80: 4349

19 Devi NR, Behera BK, Saikia AK. ACS Omega 2018; 3: 576

For reviews, see:

20a Frost CG, Chauhan KK. J. Chem. Soc., Perkin Trans 1 2000; 3015
20b Yadav JS, Antony A, George J, Subba Reddy BV. Eur. J. Org. Chem. 2010; 591
20c Cho YS, Kim HY, Cha JH, Pae AN, Koh HY, Choi JH, Chang MH. Org. Lett. 2002; 4: 2025
20d Dobbs AP, Guesné SJ. J, Martinović S, Coles SJ, Hursthouse MB. A. J. Org. Chem. 2003; 68: 7880
20e Subba Reddy BV, Sreelatha M, Kishore Ch, Borkar P, Yadav JS. Tetrahedron Lett. 2012; 53: 2748

21 Sabitha G, Reddy KB, Reddy GS. K. K, Fatima N, Yadav JS. Synlett 2005; 2347
22 CCDC 1922264 (4h) contains 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/getstructures.
23 Iida H, Fukuhara K, Murayama Y, Machiba M, Kikuchi T. J. Org. Chem. 1986; 51: 4701

24a Wagner H, Burghart J, Hull WE. Tetrahedron Lett. 1978; 3893
24b Wagner H, Burghart J. Helv. Chem. Acta 1982; 65: 739

25 Bhanu Prasad AS, Bhaskar Kanth JV, Periasamy M. Tetrahedron 1992; 48: 4623

26a Qian G, Bai M, Gao S, Chen H, Zhou S, Cheng H.-G, Yan W, Zhou Q. Angew. Chem. Int. Ed. 2018; 57: 10980
26b Serpier F, Brayer J.-L, Folléas B, Darses S. Org. Lett. 2015; 17: 5496

The melting point is not available in the reported literature:

27a Adams CE, Walker FJ, Sharpless KB. J. Org. Chem. 1985; 50: 420
27b Bandini M, Eichholzer A, Kotrusz P, Tragni M, Troisi S, Umani-Ronchi A. Adv. Synth. Catal. 2009; 351: 319
27c Hayashi R, Cook GR. Org. Lett. 2007; 9: 1311

28 Mizukami M, Wada K, Sato G, Ishii Y, Kawahara N, Nagumo S. Tetrahedron 2013; 69: 4120

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