Synthesis, Table of Contents Synthesis 2016; 48(24): 4477-4488DOI: 10.1055/s-0035-1562616 paper © Georg Thieme Verlag Stuttgart · New YorkExpedient and Diastereoselective Synthesis of Substituted 6,6a-Dihydroisoindolo[2,1-a]quinolin-11(5H)-ones Authors Author Affiliations Zainab Al-Jaroudi a Department of Chemistry, Acadia University, Wolfville, NS, B4P 2R6, Canada Prabhu P. Mohapatra a Department of Chemistry, Acadia University, Wolfville, NS, B4P 2R6, Canada T. Stanley Cameron b Department of Chemistry, Dalhousie University, Halifax, NS,B3H 4R2, Canada Email: amitabh.jha@acadiau.ca Amitabh Jha* a Department of Chemistry, Acadia University, Wolfville, NS, B4P 2R6, Canada Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) 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 Key words3-substituted N-arylisoindolinones - N-aryl-3-hydroxyisoindolinones - electrophilic aromatic substitution - 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones - intramolecular cyclization - Lewis acid Full Text References 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 Supplementary Material Supplementary Material Supporting Information (PDF) (opens in new window)
