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 2017; 49(09): 2081-2087
DOI: 10.1055/s-0036-1588385
DOI: 10.1055/s-0036-1588385
paper
Enamine-Mediated 1,3-Dipolar Cycloaddition Reaction of Curcumin Derivatives with Azides: Direct Access to 1,4,5-Trisubstituted 1,2,3-Triazoles
Further Information
Publication History
Received: 25 October 2016
Accepted after revision: 06 December 2016
Publication Date:
12 January 2017 (online)
Abstract
An enamine-mediated [3+2] organocatalytic 1,3-dipolar cycloaddition reaction of curcumin derivatives with azides has been developed. This strategy could generate 1,4,5-trisubstituted 1,2,3-triazoles in high yields and regioselectivities under mild conditions.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588385.
- Supporting Information
-
References
- 1a Pagliai F, Pirali T, Grosso ED, Brisco RD, Tron GC, Sorba G, Genazzani AA. J. Med. Chem. 2006; 49: 467
- 1b Lee T, Cho M, Ko S.-Y, Youn H.-J, Baek DJ, Cho W.-J, Kang C.-Y, Kim S. J. Med. Chem. 2007; 50: 585
- 1c Smith G, Glaser M, Perumal M, Nguyen Q.-D, Shan B, Arstad E, Aboagye EO. J. Med. Chem. 2008; 51: 8057
- 1d Yim C.-B, Dijkgraaf I, Merkx R, Versluis C, Eek A, Mulder GE, Rijkers DT. S, Boerman OC, Liskamp RM. J. J. Med. Chem. 2010; 53: 3944
- 1e Pisaneschi F, Nguyen Q.-D, Shamsaei E, Glaser M, Robins E, Kaliszczak M, Smith G, Spivey AC, Aboagye EO. Bioorg. Med. Chem. 2010; 18: 6634
- 2 Soltis MJ, Yeh HJ, Cole KA, Whittaker N, Wersto RP, Kohn EC. Drug Metab. Dispos. 1996; 24: 799
- 3a Neu HC, Fu KP. Antimicrob. Agents Chemother. 1979; 15: 209
- 3b Blackwell CC, Freimer EH, Tuke GC. Antimicrob. Agents Chemother. 1976; 10: 288
- 4 Sheng C, Zhang W. Curr. Med. Chem. 2011; 18: 733
- 5 Legat FJ, Krause R, Zenahlik P, Hoffmann C, Scholz S, Salmhofer W, Tscherpel J, Tscherpel T, Kerl H, Dittrich P. Antimicrob. Agents Chemother. 2005; 49: 4368
- 6a Pérez-Castro I, Caamaño O, Fernández F, García MD, López C, De Clercq E. Org. Biomol. Chem. 2007; 5: 3805
- 6b Kiss L, Forro E, Fulop F. Lett. Org. Chem. 2011; 8: 220
- 7a Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 565
- 7b Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 633
- 8 Huisgen R, Szeimis G, Möbius L. Chem. Ber. 1967; 100: 2494
- 9 Tornoe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
- 10a Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
-
10b Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 10c Himo F, Lovell T, Sharpless KB. J. Am. Chem. Soc. 2005; 127: 210
- 11a Nakamura T, Terashima T, Ogata K, Fukuzawa S. Org. Lett. 2011; 13: 620
- 11b Spiteri C, Moses JE. Angew. Chem. Int. Ed. 2010; 49: 31
- 11c Kappe CO, Van der Eycken E. Chem. Soc. Rev. 2010; 39: 1280
- 11d Amblard F, Cho JH, Schinazi RF. Chem. Rev. 2009; 109: 4207
- 11e Shi F, Waldo JP, Chen Y, Larock RC. Org. Lett. 2008; 10: 2409
- 11f Moses JE, Moorhouse AD. Chem. Soc. Rev. 2007; 36: 1249
- 11g Calvo-Flores FG, Isac-Garcia J, Hernández-Mateo F, Pérez-Balderas F, Calvo-Asin JA, Sanchéz-Vaquero E, Santoyo-González F. Org. Lett. 2000; 2: 2499
- 11h Pérez-Balderas F, Ortega-Muńoz M, Morales-Sanfrutos J, Hernández-Mateo F, Calvo-Flores FG, Calvo-Asin JA, Isac-Garcia J, Santoyo-González F. Org. Lett. 2003; 5: 1951
- 12a Zhang L, Chen X, Xue P, Sun HH, Williams ID, Sharpless KB, Fokin VV, Jia G. J. Am. Chem. Soc. 2005; 127: 15998
- 12b Boren BC, Narayan S, Rasmussen LK, Zhang L, Zhao H, Lin Z, Jia G, Fokin VV. J. Am. Chem. Soc. 2008; 130: 8923
- 12c Tam A, Arnold U, Soellner MB, Raines RT. J. Am. Chem. Soc. 2007; 129: 12670
-
13 For an example of IrAAC, see: Ding S, Jia G, Sun J. Angew. Chem. Int. Ed. 2014; 53: 1877
- 14a Ramaastry V. Angew. Chem. Int. Ed. 2014; 53: 14310
- 14b John J, Thomas J, Dehaen W. Chem. Commun. 2015; 51: 10797
- 14c Lima CG. S, Ali A, van Berkel SS, Westermann B, Paixão MW. Chem. Commun. 2015; 51: 10784
- 15a Thomas J, John J, Parekh N, Dehaen W. Angew. Chem. Int. Ed. 2014; 53: 10155
- 15b Ali A, Corrêa AG, Alves D, Zukerman-Schpector J, Westermann B, Ferreira MA. B, Paixão MW. Chem. Commun. 2014; 50: 11926
- 15c Cheng G, Zeng X, Shen J, Wang X, Cui X. Angew. Chem. Int. Ed. 2013; 52: 13265
- 15d van Berkel SS, Brauch S, Gabriel L, Henze M, Stark S, Vasilev D, Wessjohann LA, Abbas M, Westermann B. Angew. Chem. Int. Ed. 2012; 51: 5343
- 15e Chen Z, Yan Q, Liu Z, Xu Y, Zhang Y. Angew. Chem. Int. Ed. 2013; 52: 13324
- 15f Cai ZJ, Lu XM, Zi Y, Yang C, Shen LJ, Li J, Wang SY, Ji SJ. Org. Lett. 2014; 16: 5108
- 15g Quan XJ, Ren ZH, Wang YY, Guan ZH. Org. Lett. 2014; 16: 5728
- 15h Chen Z, Yan Q, Yi H, Liu Z, Lei A, Zhang Y. Chem. Eur. J. 2014; 20: 13692
- 15i John J, Thomas J, Parekh N, Dehaen W. Eur. J. Org. Chem. 2015; 4922
- 15j Chen Y, Nie G, Zhang Q, Ma S, Li H, Hu Q. Org. Lett. 2015; 17: 1118
- 15k Jia F, Xu C, Zhou Z, Cai Q, Li D, Wu A. Org. Lett. 2015; 17: 2820
- 15l Wei F, Li H, Song C, Ma Y, Zhou L, Tung C, Xu Z. Org. Lett. 2015; 17: 2860
- 15m Wang W, Peng X, Wei F, Tung C, Xu Z. Angew. Chem. Int. Ed. 2016; 55: 649
- 16a Ramachary DB, Ramakumar K, Narayana VV. Chem. Eur. J. 2008; 14: 9143
- 16b Ramachary DB, Shashank AB. Chem. Eur. J. 2013; 19: 13175
-
16c Ramachary DB, Shashank AB, Karthik S. Angew. Chem. Int. Ed. 2014; 53: 10420
- 16d Shashank AB, Karthik S, Madhavachary R, Ramachary DB. Chem. Eur. J. 2014; 20: 16877
- 16e Krishna PM, Ramachary DB, Peesapati S. RSC Adv. 2015; 5: 62062
- 16f Ramachary DB, Krishna PM, Gujral J, Reddy GS. Chem. Eur. J. 2015; 21: 16775
- 17 Belkheira M, El Abed D, Pons J.-M, Bressy C. Chem. Eur. J. 2011; 17: 12917
- 18a Danence LJ. T, Gao Y, Li M, Huang Y, Wang J. Chem. Eur. J. 2011; 17: 3584
- 18b Wang L, Peng SY, Danence LJ. T, Gao Y, Wang J. Chem. Eur. J. 2012; 18: 6088
- 18c Li WJ, Jia QF, Du ZY, Wang J. Chem. Commun. 2013; 49: 10187
- 18d Yeung DK. J, Gao T, Huang JY, Sun SF, Guo HB, Wang J. Green Chem. 2013; 15: 2384
- 18e Wang L, Huang JY, Gong XJ, Wang J. Chem. Eur. J. 2013; 19: 7555
- 18f Li WJ, Du ZY, Huang JY, Jia QF, Zhang K, Wang J. Green Chem. 2014; 16: 3003
- 18g Li WJ, Wang J. Angew. Chem. Int. Ed. 2014; 53: 14186
- 18h Li WJ, Du ZY, Zhang K, Wang J. Green Chem. 2015; 17: 781
- 18i Jia QF, Yang GM, Chen L, Du ZY, Wei J, Zhong Y, Wang J. Eur. J. Org. Chem. 2015; 3435
- 18j Li WJ, Zhou X, Luan Y, Wang J. RSC Adv. 2015; 5: 88816
- 19a Weber WM, Hunsaker LA, Roybal CN, Bobrovnikova-Marjon EV, Abcouwer SF, Royer RE, Deck LM, Vander Jagt DL. Bioorg. Med. Chem. 2006; 14: 2450
- 19b Hong J, Bose M, Ju J, Ryu J, Chen X, Sang S, Lee M, Yang C. Carcinogenesis 2004; 25: 1671
- 19c Woo HB, Shin W, Lee S, Ahn CM. Bioorg. Med. Chem. Lett. 2005; 15: 3782
- 20a Ahn CM, Shin WS, Woo HB, Lee S, Lee HW. Bioorg. Med. Chem. Lett. 2004; 14: 3893
- 20b Venkateswarlu S, Ramachandra MS, Subbaraju GV. Bioorg. Med. Chem. 2005; 13: 6374
- 20c Mishra S, Karmodiya K, Surolia A. Bioorg. Med. Chem. 2008; 16: 2894
- 21a Li W, Wu W, Yu F, Huang H, Liang X, Ye J. Org. Biomol. Chem. 2011; 9: 2505
- 21b Ayyagari N, Jose D, Mobin SM, Namboothiri IN. N. Tetrahedron Lett. 2011; 52: 258
- 21c Ayyagari N, Namboothiri IN. N. Tetrahedron: Asymmetry 2012; 23: 605
- 21d Yin X.-G, Liu X.-Y, Hu Z.-P, Yan M. Org. Biomol. Chem. 2012; 10: 1506
- 21e Luo N, Sun X, Wei W, Zhang XJ, Yan M. Tetrahedron: Asymmetry 2013; 24: 402
- 22a Lev AS, Strier L, Kazanov D, Arber N. Clin. Cancer Res. 2005; 11: 6738
- 22b Handler N, Jaeger W, Erker T. Chem. Pharm. Bull. 2007; 55: 64
For selected examples of RuAAC, see:
For a recent highlight and reviews on 1,2,3-triazole synthesis, see:
For selected examples of 1,2,3-triazole synthesis, see: