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Synthesis 2014; 46(17): 2327-2332
DOI: 10.1055/s-0033-1339120
DOI: 10.1055/s-0033-1339120
paper
Synthesis of (Triphenylphosphoranylidene)spiro[cyclopentene-1,3′-indole]s by a Three-Component Reaction of Triphenylphosphine, Dialkyl Acetylenedicarboxylates, and 3-(Aroylmethylene)-1,3-dihydro-2H-indol-2-ones
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Further Information
Publication History
Received: 14 February 2014
Accepted after revision: 22 April 2014
Publication Date:
28 May 2014 (online)
Abstract
The three-component reaction of triphenylphosphine, a dialkyl acetylenedicarboxylate, and a 3-(aroylmethylene)-1,3-dihydro-2H-indol-2-one in 1,2-dimethoxyethane at room temperature gave the corresponding functionalized (triphenylphosphoranylidene)spiro[cyclopentene-1,3′-indole]s in satisfactory yields.
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10.1055/s-00000084.
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References
- 1a Huisgen R, Morikawa M, Herbig K, Brunn E. Chem. Ber. 1967; 100: 1094
- 1b Huisgen R. Z. Chem. 1968; 8: 290
- 2a Johnson AW, Tebby JC. J. Chem. Soc. 1961; 2126
- 2b Tebby JC, Wilson IF, Griffiths DV. J. Chem. Soc., Perkin Trans. 1 1979; 2133
- 3 Lu X, Zhang C, Xu Z. Acc. Chem. Res. 2001; 34: 535
- 4a Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L. Acc. Chem. Res. 2003; 36: 899
- 4b Nair V, Menon RS, Sreekanth A, Abhilash N, Biju AT. Acc. Chem. Res. 2006; 39: 520
- 5a Kielland N, Lavilla R. Top. Heterocycl. Chem. 2010; 25: 127
- 5b Shaabani A, Rezayan AH, Sarvary A. Mol. Diversity 2011; 15: 41
- 6a Nair V, Nair JS, Vinod AU. J. Chem. Soc., Perkin Trans. 1 1998; 3129
- 6b Nair V, Nair JS, Vinod AU. Synthesis 2000; 1713
- 6c Nair V, Deepthi A, Beneesh PB, Eringathodi S. Synthesis 2006; 1443
- 7a Zhu G, Chen Z, Jiang Q, Xiao D, Cao P, Zhang X. J. Am. Chem. Soc. 1997; 119: 3836
- 7b Du Y, Lu X. J. Org. Chem. 2003; 68: 6463
- 7c Zhu X.-F, Lan J, Kwon O. J. Am. Chem. Soc. 2003; 125: 4716
- 7d Tran YS, Kwon O. Org. Lett. 2005; 7: 4289
- 7e Jung C.-K, Wang JC, Krische MJ. J. Am. Chem. Soc. 2004; 126: 4118
- 8a Ramazani A, Noshiranzadeh N, Ghamkharia A, Ślepokura K, Lis T. Helv. Chim. Acta 2008; 91: 2252
- 8b Yavari I, Mohtat B, Zare H. Mendeleev Commun. 2006; 16: 102
- 8c Alizadeh A, Sheikhi E. Tetrahedron Lett. 2007; 48: 4887
- 8d Asghari S, Tajbakhsh M, Taghipour V. Tetrahedron Lett. 2008; 49: 1824
- 9a Yavari A, Moradi L. Tetrahedron Lett. 2006; 47: 1627
- 9b Adib M, Sayahi MH, Mahernia S, Zhu L.-G. Tetrahedron Lett. 2008; 49: 945
- 9c Heydari R, Maghsoodlou MT, Yami RN. Chin. Chem. Lett. 2009; 20: 1175
- 9d Alizadeh A, Rostamnia S, Zhu LG. Tetrahedron Lett. 2010; 51: 4750
- 10a Deng H.-P, Wei Y, Shi M. Org. Lett. 2011; 13: 3348
- 10b Zhang X.-C, Kao S.-H, Wei Y, Shi M. Org. Lett. 2011; 13: 1142
- 10c Zhang X.-C, Kao S.-H, Wei Y, Shi M. Chem. Commun. 2011; 47: 1548
Reference Ris Wihthout Link
- 11a Methot JL, Roush WR. Adv. Synth. Catal. 2004; 346: 1035
- 11b Marinetti A, Voituriez A. Synlett 2010; 174
- 11c Wei Y, Shi M. Acc. Chem. Res. 2010; 43: 1005
- 12a Ye L.-W, Zhou J, Tang Y. Chem. Soc. Rev. 2008; 37: 1140
- 12b Cowen BJ, Miller SJ. Chem. Soc. Rev. 2009; 38: 3102
- 12c Xu S, He Z. Zhongguo Kexue: Huaxue 2010; 40: 856
- 13a Kotha S, Deb AC, Lahiri K, Manivannan E. Synthesis 2009; 165
- 13b Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
- 13c Liu Y, Wang H, Wan J. Asian J. Org. Chem. 2013; 2: 374
- 14a Trost BM, Brennan MK. Synthesis 2009; 3003
- 14b Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165
- 14c Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
- 14d Cheng D, Ishihara Y, Tan B, Barbas III CF. ACS Catal. 2014; 4: 743
- 15a Esmaeili AA, Bodaghi A. Tetrahedron 2003; 59: 1169
- 15b Esmaeili AA, Darbanian M. Tetrahedron 2003; 59: 5545
- 15c Nair V, Vinod AU, Abhilash N, Menon RS, Santhi V, Varma RL, Viji S, Mathew S, Srinivas R. Tetrahedron 2003; 59: 10279
- 15d Yavari I, Hossaini Z, Sabbaghan M, Ghazanfarpour-Darjani M. Tetrahedron 2007; 63: 9423
- 15e Nair V, Devipriya S, Suresh E. Tetrahedron 2008; 64: 3567
- 16a Esmaeili AA, Nazer M. Synlett 2009; 2119
- 16b Esmaeili AA, Vesalipoor H, Hosseinabadi R, Zavareh AF, Naseri NA, Ghiamati E. Tetrahedron Lett. 2011; 52: 4865
- 16c Kiruthika SE, Lakshmi NV, Banu BR, Perumal PT. Tetrahedron Lett. 2011; 52: 6508
- 17a Sun J, Xia E.-Y, Wu Q, Yan C.-G. Org. Lett. 2010; 12: 3678
- 17b Sun J, Xia E.-Y, Wu Q, Yan C.-G. ACS Comb. Sci. 2011; 13: 421
- 17c Sun J, Sun Y, Xia E.-Y, Yan C.-G. ACS Comb. Sci. 2011; 13: 436
- 17d Sun J, Wu Q, Xia E.-Y, Yan C.-G. Eur. J. Org. Chem. 2011; 2981
- 18a Sun J, Sun Y, Gong H, Xie Y.-J, Yan C.-G. Org. Lett. 2012; 14: 5172
- 18b Han Y, Sun Y, Sun J, Yan C.-G. Tetrahedron 2012; 68: 8256
- 18c Sun J, Sun Y, Gao H, Yan C.-G. Eur. J. Org. Chem. 2012; 1976
- 18d Han Y, Wu Q, Sun J, Yan C.-G. Tetrahedron 2012; 68: 8539
- 18e Sun J, Zhu D, Gong H, Yan C.-G. Tetrahedron 2013; 69: 10565
- 18f Gao H, Sun J, Yan C.-G. Tetrahedron 2013; 69: 589
- 19 Crystallographic data for compounds 1e, 1h, and 1k have been deposited with the accession numbers CCDC 982781, 982782, and 982783, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.