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Synthesis 2016; 48(24): 4477-4488
DOI: 10.1055/s-0035-1562616
DOI: 10.1055/s-0035-1562616
paper
Expedient and Diastereoselective Synthesis of Substituted 6,6a-Dihydroisoindolo[2,1-a]quinolin-11(5H)-ones
Further Information
Publication History
Received: 20 May 2016
Accepted after revision: 17 July 2016
Publication Date:
07 September 2016 (online)
Abstract
Further synthetic utility of 3-substituted N-arylisoindolinones obtained from N-aryl-3-hydroxyisoindolinones and alkyl aryl ketones under Lewis acid mediated anhydrous conditions is reported. Herein, substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones were synthesized from 3-substituted isoindolinones following a NaBH4 ketone reduction and carbocation-mediated intramolecular electrophilic aromatic substitution using BF3·OEt2. Representative final products were unambiguously characterized by single-crystal X-ray crystallography.
Key words
3-substituted N-arylisoindolinones - N-aryl-3-hydroxyisoindolinones - electrophilic aromatic substitution - 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones - intramolecular cyclization - Lewis acidSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562616.
- Supporting Information
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References
- 1 Valencia E, Freyer AJ, Shamma M, Fajardo V. Tetrahedron Lett. 1984; 25: 599
- 2 Moreau A, Couture A, Deniau E, Grandclaudon P. Eur. J. Org. Chem. 2005; 3437
- 3 Apers S, Vlietinck A, Pieters L. Phytochem. Rev. 2003; 2: 201
- 4 Ishihara Y, Kiyota Y, Goto G. Chem. Pharm. Bull. 1990; 38: 3024
- 5 Sui Z, Altom J, Nguyen VN, Fernandez J, Bernstein JI, Hiliard JJ, Barrett JF, Podlogar BL, Ohemeng KA. Bioorg. Med. Chem. 1998; 6: 735
- 6 Pigeon P, Othman M, Netchitaïlo P, Decroix B. J. Heterocycl. Chem. 1999; 36: 691
- 7 Epsztajn J, Jóźwiak A, Kołuda P, Sadokierska I, Wilkowska ID. Tetrahedron 2000; 56: 4837
- 8 Varlamov AV, Zubkov FI, Boltukhina EV, Sidorenko NV, Borisov RS. Tetrahedron Lett. 2003; 44: 3641
- 9 Varlamov AV, Boltukhina EV, Zubkov FI, Nikitina EV, Turchin KF. J. Heterocycl. Chem. 2006; 43: 1479
- 10 Zubkov FI, Boltukhina EV, Turchin KF, Borisov RS, Varlamov AV. Tetrahedron 2005; 61: 4099
- 11 Zhang W, Zheng A, Liu Z, Yang L, Liu Z. Tetrahedron Lett. 2005; 46: 5691
- 12 Mamane V, Fort Y. Tetrahedron Lett. 2006; 47: 2337
- 13 Zhang W, Zhou Y, Qian L. Synlett 2009; 843
- 14 Khadem S, Udachin KA, Enright GD, Prakesch M, Arya P. Tetrahedron Lett. 2009; 50: 6661
- 15 Qiao L, Zhou Y, Zhang W. Chin. J. Chem. 2010; 28: 449
- 16 Merchan Arenas DR, Rojas Ruíz FA, Kouznetsov VV. Tetrahedron Lett. 2011; 52: 1388
- 17 Merchan Arenas DR, Kouznetsov VV. J. Org. Chem. 2014; 79: 5327
- 18 Jha A, Chou TY, Aljaroudi Z, Ellis BD, Cameron TS. Beilstein J. Org. Chem. 2014; 10: 848
- 19 Jha A, Dimmock JR. Can. J. Chem. 2003; 81: 293
- 20 Nichols CE, Youssef D, Harris RG, Jha A. ARKIVOC 2006; (xiii): 64
- 21 Huang P.-JJ, Youssef D, Cameron TS, Jha A. ARKIVOC 2008; (xvi): 165
- 22 Pericherla K, Kumar A, Jha A. Org. Lett. 2013; 15: 4078
- 23 Huang P.-JJ, Potter E, Jha A. Mol. Divers. 2010; 14: 393
- 24 Abdelkhalik AM, Paul NK, Jha A. Steroids 2015; 98: 117
- 25 Aljaroudi Z, Mohapatra PP, Jha A. Tetrahedron Lett. 2016; 57: 772
- 26 CCDC 1450475 (3a), 1450447 (3c′), and 1450448 (3f) 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/getstructures.
- 27 Dhanasekaran S, Kayet A, Suneja A, Bisai V, Singh VK. Org. Lett. 2015; 17; 2780