Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(3): 375-381
DOI: 10.1055/s-0032-1316836
DOI: 10.1055/s-0032-1316836
paper
Three-Component Condensation for the Construction of Novel Spirooxindoles
Further Information
Publication History
Received: 13 November 2012
Accepted after revision: 05 December 2012
Publication Date:
21 December 2012 (online)
Abstract
A new route for the synthesis of novel spirooxindoles from isocyanides, dialkyl acetylenedicarboxylates, and N-substituted isatylidene derivatives through [3+2] cycloaddition has been developed. This method has several advantages, such as high regioselectivity, high yields, readily available starting materials, and one-pot operations. The synthetic alkyne-containing spirooxindoles could also be used in the selective synthesis of triazole-containing spirocyclic compounds using a copper azide–alkyne cycloaddition (CuAAC) reaction.
Key words
multicomponent reaction - spirooxindoles - [3+2] cycloaddition - CuAAC reaction - triazolesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
Primary Data
- for this article are available online at http://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0036th
- Primary Data
-
References
- 1a Williams RM, Cox RJ. Acc. Chem. Res. 2003; 36: 127
-
1b Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
- 2a Trost BM, Jiang C. Synthesis 2006; 369
- 2b Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2209
- 2c Chen XH, Wei Q, Xiao H, Luo SW, Gong LZ. J. Am. Chem. Soc. 2009; 131: 13819
- 2d Bencivenni G, Wu LY, Mazzanti A, Giannichi B, Pesciaioli F, Song MP, Bartoli G, Melchiorre P. Angew. Chem. Int. Ed. 2009; 48: 7200
- 2e Wei Q, Gong LZ. Org. Lett. 2010; 12: 1008
- 2f Shintani R, Hayashi SY, Murakami M, Takeda M, Hayashi T. Org. Lett. 2009; 11: 3754
- 2g Castaldi MP, Troast DM, Porco JA. Org. Lett. 2009; 11: 3362
- 3a Ruijter E, Scheffelaar R, Orru RV. A. Angew. Chem. Int. Ed. 2011; 50: 6234
- 3b Bienayme H, Hulme C, Oddon G, Schmitt P. Chem. Eur. J. 2000; 6: 3321
- 4a Oakes TR, David HG, Nagel FJ. J. Am. Chem. Soc. 1969; 91: 4761
- 4b Takizawa T, Obata N, Suzuki Y, Yanagida T. Tetrahedron Lett. 1969; 10: 3407
- 4c Ugi I. Angew. Chem., Int. Ed. Engl. 1982; 21: 810
- 4d Yavari I, Maghsoodlou MT. J. Chem. Res., Synop. 1998; 386
- 5a Reddy BV. S, Reddy AM, Somashekar D, Yadav JS, Sridhar B. Synthesis 2010; 2571
- 5b Terzidis MA, Stephanidou-Stephanatou J, Tsoleridis CA. J. Org. Chem. 2010; 75: 1948
- 6a Shaabani A, Sarvary A, Ghasemi S, Rezayan AH, Ghadari R, Ng SW. Green Chem. 2011; 13: 582
- 6b Adib M, Sayahi MH, Nosrati M, Zhu LG. Tetrahedron Lett. 2007; 48: 4195
- 6c Yavari I, Alizadeh A, Anary-Abbasinejad M, Bijanzadeh HR. Tetrahedron 2003; 59: 6083
- 7a Alizadeh A, Rostamnia S. Synthesis 2008; 57
- 7b Baharfar R, Jaafari L, Azimi R. Chin. Chem. Lett. 2011; 22: 943
- 8a Alizadeh A, Oskueyan Q, Rostamnia S, Ghanbari-Niaki A, Mohebbi AR. Synthesis 2008; 2929
- 8b Alizadeh A, Rostamnia S, Zhu LG. Synthesis 2008; 1788
- 8c Alizadeh A, Rostamnia S, Zhu LG. Tetrahedron 2006; 62: 5641
- 8d Alizadeh A, Rostamnia S, Hu ML. Synlett 2006; 1592
- 8e Azuaje J, Coelho A, Maatougui AE, Blanco JM, Sotelo E. ACS Comb. Sci. 2011; 13: 89
- 9a Shaabani A, Sarvary A, Rezayan AH, Keshipour S. Tetrahedron 2009; 65: 3492
- 9b Shaabani A, Ghadari R, Sarvary A, Rezayan AH. J. Org. Chem. 2009; 74: 4372
- 10 Esmaeili AA, Darbanian M. Tetrahedron 2003; 59: 5545
- 11 Yavari I, Hossaini Z, Sabbaghan M. Monatsh. Chem. 2007; 138: 107
- 12a Esmaeili AA, Moradi A, Habibi A. Synlett 2011; 2307
- 12b Nair V, Menon RS, Beneesh PB, Sreekumar V, Bindu S. Org. Lett. 2004; 6: 767
- 12c Shaabani A, Rezayan AH, Rahmati A, Sarvary A. Synlett 2007; 1458
- 13a Pibiri I, Buscemi S. Curr. Bioact. Compd. 2010; 6: 208
- 13b Tripathi RP, Yadav AK, Ajay A, Bisht SS, Chaturvedi V, Sinha SK. Eur. J. Med. Chem. 2010; 45: 142
- 13c Siddiqui N, Ahsan W, Alam MS, Ali R, Jain S, Azad B, Akhtar J. Int. J. Pharm. Sci. Rev. Res. 2011; 8: 161
-
14a Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 14b Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
-
14c Meldal M, Tornøe CW. Chem. Rev. 2008; 108: 2952
- 14d Niu TF, Gu L, Yi WB, Cai C. ACS Comb. Sci. 2012; 14: 309
- 14e MacDonald JP, Badillo JJ, Arevalo GE, Silva-García A, Franz AK. ACS Comb. Sci. 2012; 14: 285
For reviews on domino reactions, see: