RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2014; 46(08): 1059-1066
DOI: 10.1055/s-0033-1340815
DOI: 10.1055/s-0033-1340815
paper
Facile Synthesis of Spiro[indane-2,1′-pyrrolo[2,1-a]isoquinolines] via Three-Component Reaction of Isoquinolinium Salts, Indane-1,3-dione, and Isatins
Weitere Informationen
Publikationsverlauf
Received: 24. Dezember 2013
Accepted after revision: 22. Januar 2014
Publikationsdatum:
10. Februar 2014 (online)
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
spiro compound - isoquinoline - isatin - indane-1,3-dione - nitrogen ylide - 1,3-cycloadditionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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