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
PDF herunterladen
Synthesis 2014; 46(04): 489-495
DOI: 10.1055/s-0033-1340459
DOI: 10.1055/s-0033-1340459
paper
Povarov Reaction of β-Enamino Esters and Isatin-3-imines for Diastereoselective Synthesis of Spiro[indoline-3,2′-quinolines]
Weitere Informationen
Publikationsverlauf
Received: 22. Oktober 2013
Accepted after revision: 18. November 2013
Publikationsdatum:
10. Dezember 2013 (online)
Abstract
The p-toluenesulfonic acid catalyzed Povarov reaction of isatin-3-imines with β-enamino esters, which were generated in situ from the reaction of arylamines and methyl propiolate in ethanol, afforded the polysubstituted spiro[indoline-3,2′-quinolines] in high yields and with high diastereoselectivity.
Key words
Povarov reaction - hetero-Diels–Alder reaction - β-enamino ester - isatinimine - spiro[indoline-3,2′-quinolines]Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Povarov LS. Russ. Chem. Rev. 1967; 36: 656
- 2a Buonora P, Olsen JC, Oh T. Tetrahedron 2001; 57: 6099
- 2b Syamal M. Org. Prep. Proced. Int. 2005; 37: 103
- 2c Choudhury LH, Parvin T. Tetrahedron 2011; 67: 8213
- 3a Bello D, Ramon R, Lavilla R. Curr. Org. Chem. 2010; 14: 332
- 3b Kouznetsov VV. Tetrahedron 2009; 65: 2721
- 3c Majumdar KC, Taher A, Nandi RK. Tetrahedron 2012; 68: 5693
- 4a Palacios A, Herran E, Alonso C, Rubiales G. Tetrahedron 2006; 62: 7661
MissingFormLabel
- 4b Alves MJ, Azoia NG, Fortes AG. Tetrahedron 2007; 63: 727
- 4c Jin GF, Zhao JW, Han JW, Zhu SZ, Zhang JM. Tetrahedron 2010; 66: 913
- 5a Maiti G, Kundu P. Tetrahedron Lett. 2006; 47: 5733
- 5b Chen ZL, Lin LL, Chen DH, Li JT, Liu XH, Feng XM. Tetrahedron Lett. 2010; 51: 3088
- 5c Rajanarendar E, Reddy MN, Reddy KG, Krishna SR. Tetrahedron Lett. 2012; 53: 2909
- 6a Kouznetsov VV, Mora Cruz U, Zubkov FI, Nikitina EV. Synthesis 2007; 375
- 6b Kouznestov VV, Romero Bohorquez AR, Astudillo Saavedra L, Fierro Medina R. Mol. Diversity 2006; 10: 29
- 6c Sridharan V, Suryavanshi PA, Menendez JC. Chem. Rev. 2011; 111: 7157
- 7a Demaude T, Knerr L, Pasau P. J. Comb. Chem. 2004; 6: 768
- 7b Kobayashi S, Nagayama S. J. Am. Chem. Soc. 1996; 118: 8977
- 8a Tietze LF. Chem. Rev. 1996; 96: 115
- 8b Beifuss U, Herde A, Ledderhose S. Chem. Commun. 1996; 1213
- 8c Laschat S, Lauterweine J. J. Org. Chem. 1993; 58: 2856
- 8d Anniyappan M, Muralidharan D, Perumal PT. Tetrahedron Lett. 2003; 44: 3653
- 8e Muhuni J, Spaller MR. J. Org. Chem. 2006; 71: 5515
- 9a Yadav JS, Subba Reddy BV, Madhurai CR, Sabitha G. Synthesis 2001; 1065
- 9b Kouznetsov VV, Gómez CM, Ruíz FR, del Olmo E. Tetrahedron Lett. 2012; 53: 3115
- 9c Maiti G, Karmakar R, Kayal U. Tetrahedron Lett. 2013; 54: 2920
- 10a Cabral J, Laszlo P, Montaufier MT. Tetrahedron Lett. 1988; 29: 547
- 10b Spanedda MV, Hoang VD, Crousse B, Bonnet-Delphon D, Begue JP. Tetrahedron Lett. 2003; 44: 217
- 11a Chen DS, Li YL, Liu Y, Wang XS. Tetrahedron 2013; 69: 7045
- 11b Rong ZT, Li QJ, Jia YX. Tetrahedron Lett. 2013; 54: 4432
- 12a Lue P, Greenhill JV. Adv. Heterocycl. Chem. 1997; 67: 215
- 12b Elassara AZ, El-Khair AA. Tetrahedron 2003; 59: 8463
- 13a Fenain F, Médebielle M, Rocher M, Onomura O, Okada E, Shibata D. J. Fluorine Chem. 2007; 128: 1286
- 13b Yavari I, Hossaini Z, Sabbaghan M. Tetrahedron Lett. 2008; 49: 844
- 13c Vicario J, Aparicio D, Palacios F. Tetrahedron Lett. 2011; 52: 4109
- 13d Lyutenko NV, Gerus II. Tetrahedron Lett. 2013; 54: 4091
- 14a Sun J, Xia EY, Wu Q, Yan CG. Org. Lett. 2010; 12: 678
- 14b Sun J, Wu Q, Xia EY, Yan CG. Eur. J. Org. Chem. 2011; 2981
- 14c Sun J, Xia EY, Wu Q, Yan CG. ACS Comb. Sci. 2011; 13: 421
- 14d Sun J, Sun Y, Xia EY, Yan CG. ACS Comb. Sci. 2011; 13: 436
- 14e Sun J, Sun Y, Gao H, Yan CG. Synthesis 2012; 44: 1069
- 15 Sun J, Gao H, Wu Q, Yan CG. Beilstein J. Org. Chem. 2012; 8: 1839
- 16a Shi YH, Wang Z, Shi Y, Deng WP. Tetrahedron 2012; 68: 3649
- 16b Reddy SB.V, Karthik G, Rajasekaran T, Antony A, Sridhar B. Tetrahedron Lett. 2012; 53: 2396
- 16c Chauhan P, Chimni SH. Tetrahedron: Asymmetry 2013; 24: 343
- 16d Periyaraja S, Shanmugam P, Mandal AB, Kumar TS, Ramamurthy P. Tetrahedron 2013; 69: 2891
- 17a Kouznetsov VV, Forero VS. B, Torres DF.A. Tetrahedron Lett. 2008; 49: 5855
- 17b Shi F, Xing GJ, Zhu RY, Tan W, Tu SJ. Org. Lett. 2013; 15: 128
- 18 CCDC 933878 and CCDC 971471 contain the supplementary crystallographic data for compounds 1d and 1e, respectively, of this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.