Synthesis, Table of Contents Synthesis 2014; 46(08): 1059-1066DOI: 10.1055/s-0033-1340815 paper © Georg Thieme Verlag Stuttgart · New YorkFacile Synthesis of Spiro[indane-2,1′-pyrrolo[2,1-a]isoquinolines] via Three-Component Reaction of Isoquinolinium Salts, Indane-1,3-dione, and Isatins Authors Author Affiliations Xiao-Hua Wang College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. of China Fax: +86(514)87975244 Email: cgyan@yzu.edu.cn Chao-Guo Yan* College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. of China Fax: +86(514)87975244 Email: cgyan@yzu.edu.cn Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract A series of novel 2′-aryl-2′-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)-2′,3′-dihydro-10b′H-spiro[indene-2,1′-pyrrolo[2,1-a]isoquinoline]-1,3-diones were efficiently synthesized by three-component reactions of in situ generated N-phenacylisoquinolinium bromides with indane-1,3-dione and isatins in ethanol with triethylamine as the base. A domino reaction mechanism for the formation of the spiro compounds was rationally proposed. Key words Key wordsspiro compound - isoquinoline - isatin - indane-1,3-dione - nitrogen ylide - 1,3-cycloaddition Full Text References References 1a Kröhnke F, Zecher W. Angew. Chem. Int. Ed. 1962; 1: 626 1b Kröhnke F. Angew. Chem. Int. Ed. 1963; 2: 225 2 Jacobs J, Van Hende E, Claessens S, De Kimpe N. Curr. Org. Chem. 2011; 15: 1340 3a Wang BX, Zhang XC, Li J, Jiang X, Hu YF, Hu HW. J. Chem. Soc., Perkin Trans. 1 1999; 1571 3b Hu JX, Jiang X, He T, Zhou J, Hu YF, Hu HW. J. Chem. Soc., Perkin Trans. 1 2001; 1820 4a Kojima S, Suzuki M, Watanabe A, Ohkata K. Tetrahedron Lett. 2006; 47: 9061 4b Kojima S, Hiroike K, Ohkata K. Tetrahedron Lett. 2004; 45: 3565 4c Kojima S, Fujitomo K, Shinohara Y, Shimizu M, Ohkata K. Tetrahedron Lett. 2000; 41: 9847 4d Yamada S, Yamamoto J, Ohta E. Tetrahedron Lett. 2007; 48: 855 5a Shang YJ, Zhang M, Yu SY, Ju K, Wang CE, He XW. Tetrahedron Lett. 2009; 50: 6981 5b Muthusaravanan S, Perumal S, Yogeeswari P, Sriram D. Tetrahedron Lett. 2010; 51: 6439 5c Gogoi S, Dutta M, Gogoi J, Boruah RC. Tetrahedron Lett. 2011; 52: 813 5d Proença F, Costa M. Tetrahedron 2011; 67: 1071 5e Bloch WM, Derwent-Smith SM, Issa F, Morris JC, Rendina LM, Sumby CJ. Tetrahedron 2011; 67: 9368 6a Mao ZJ, Li XJ, Lin XF, Lu P, Wang YG. Tetrahedron 2012; 68: 85 6b Yang Y, Gao M, Zhang DX, Wu LM, Shu WM, Wu AX. Tetrahedron 2012; 68: 7338 6c Peláez WJ, Pinho e Melo T. Tetrahedron 2013; 69: 3646 6d Khoroshilov GE, Tverdokhleb NM, Brovarets VS, Babaev EV. Tetrahedron 2013; 69: 4353 6e Dontsova NE, Nesterov VN, Shestopalov AM. Tetrahedron 2013; 69: 5016 6f Paira R, Mondal S, Chowdhury A, Banerjee M, Maity A, Hazra A, Mondal NB. Tetrahedron Lett. 2013; 54: 3046 7a Neogi A, Majhi TP, Mukhopadhyay R, Chattopadhyay P. J. Org. Chem. 2006; 71: 3291 7b Rujirawanich J, Gallagher T. Org. Lett. 2009; 11: 5494 7c Ullah E, Rotzoll S, Schmidt A, Michalikc D, Langer P. Tetrahedron Lett. 2005; 46: 8997 8a Moghaddam FM, Mirjafary Z, Saeidian H, Taheri S, Doulabi M, Kiamehr M. Tetrahedron 2010; 66: 134 8b Moghaddam FM, Taheri S, Mirjafary Z, Saeidian H. Synlett 2010; 123 8c Moghaddam FM, Mirjafary M, Saeidian H, Taheria S, Soltanzadeh B. Tetrahedron 2010; 66: 3678 8d Moghaddam FM, Mirjafary Z, Saeidian H, Taheri S, Khodabakhshi MR. Tetrahedron Lett. 2010; 51: 2704 8e Kiamehr M, Moghaddam FM, Gormay PV, Semeniuchenko V, Villinger A, Langer P, Iaroshenko VO. Tetrahedron 2012; 68: 9685 9 Paira R, Mondal S, Maity A, Sahu KB, Naskar S, Saha P, Hazra A, Kundu S, Banerjee S, Mondal NB. Tetrahedron Lett. 2011; 52: 5516 10a Yan CG, Cai XM, Wang QF, Wang TY, Zheng M. Org. Biomol. Chem. 2007; 5: 945 10b Yan CG, Song XK, Wang QF, Sun J, Siemeling U, Bruhn C. Chem. Commun. 2008; 1440 10c Wang QF, Song XK, Chen J, Yan CG. J. Comb. Chem. 2009; 11: 1007 10d Wang QF, Hou H, Hui L, Yan CG. J. Org. Chem. 2009; 74: 7403 10e Yan CG, Wang QF, Song XK, Sun J. J. Org. Chem. 2009; 74: 710 11a Wang QF, Hui L, Hou H, Yan CG. J. Comb. Chem. 2010; 12: 260 11b Han Y, Chen J, Hui L, Yan CG. Tetrahedron 2010; 66: 7743 11c Hou H, Zhang Y, Yan CG. Chem. Commun. 2012; 48: 4492 12a Nyerges M, Gajdics L, Szöllösy A, Töke L. Synlett 1999; 111 12b Fejes I, Töke L, Nyerges M, Pak CS. Tetrahedron 2000; 56: 639 12c Fejes I, Nyerges M, Szollosy A, Blasko G, Töke L. Tetrahedron 2001; 57: 1129 13a Serov AB, Kartsev VG, Aleksandrov AYu, Dolgushin FM. Russ. Chem. Bull. 2005; 54: 2432 13b Velikorodov AV, Imasheva NM, Kuanchalieva AK, Poddubnyi OYu. Russ. J. Org. Chem. 2010; 46: 971 14a Kotha SB, Deb AC, Lahiri K, Manivannan E. Synthesis 2009; 165 14b Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104 14c Liu YY, Wang H, Wan JP. Asian J. Org. Chem. 2013; 2: 374 15a Trost BM, Brennan MK. Synthesis 2009; 3003 15b Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165 15c Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023 16 Hui L, Li HY, Yan CG. Eur. J. Org. Chem. 2012; 3157 17 Wu L, Sun J, Yan CG. Org. Biomol. Chem. 2012; 10: 9452 18 Fu Q, Yan CG. Tetrahedron 2013; 69: 5841 19 Afsah EM, Etman HA, Hamama WS, Sayed-Ahmed AF. Boll. Chim. Farm. 1998; 137: 244 Supplementary Material Supplementary Material Supporting Information (PDF)