A New Synthetic Protocol for One-Pot Preparations of 5-Halo-1,4-disubstituted-1,2,3-triazoles
Lingjun Li A B , Yanyan Li A , Ran Li A , Anlian Zhu A and Guisheng Zhang A
+ Author Affiliations
- Author Affiliations
A College of Chemistry and Environmental Science, Henan Normal University, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Xinxiang 453007, China.
B Corresponding author. Email: lingjunlee@htu.cn
Australian Journal of Chemistry 64(10) 1383-1389 https://doi.org/10.1071/CH11067
Submitted: 11 February 2011 Accepted: 2 June 2011 Published: 23 August 2011
Abstract
In this paper, a new synthetic protocol for one-pot preparations of 5-halo-1,4-disubstituted-1,2,3-triazoles is provided by rational combination of a CuI catalyzed azide–alkyne cycloaddition (CuAAC) reaction and an oxidative halogenation reaction. CuI- N-chlorosuccinimide (NCS) and CuBr-NCS reaction systems are developed, respectively, for effective preparations of 5-iodo-1,4-disubstituted-1,2,3-triazoles and 5-bromo-1,4-disubstituted-1,2,3-trizoles under mild conditions with a high tolerance of various sensitive groups.
References
[1] (a) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004.| Crossref | GoogleScholarGoogle Scholar |
(b) H. C. Kolb, K. B. Sharpless, Drug Discov. Today 2003, 8, 1128.
| Crossref | GoogleScholarGoogle Scholar |
[2] C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057.
| Crossref | GoogleScholarGoogle Scholar |
[3] V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596.
| Crossref | GoogleScholarGoogle Scholar |
[4] M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952.
| Crossref | GoogleScholarGoogle Scholar |
[5] V. D. Bock, H. Hiemstra, J. H. Maarseveen, Eur. J. Org. Chem. 2006, 71, 51.
| Crossref | GoogleScholarGoogle Scholar |
[6] G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba, A. A. Genaz-zani, Med. Res. Rev. 2008, 28, 278.
| Crossref | GoogleScholarGoogle Scholar |
[7] F. Amblard, J. H. Hyun Cho, R. F. Schinazi, Chem. Rev. 2009, 109, 4207.
| Crossref | GoogleScholarGoogle Scholar |
[8] K. V. Hänni, D. V. Leigh, Chem. Soc. Rev. 2010, 39, 1240.
| Crossref | GoogleScholarGoogle Scholar |
[9] A. Dondoni, A. Marra, Chem. Rev. 2010, 110, 4949.
| Crossref | GoogleScholarGoogle Scholar |
[10] M. van Dijk, D. T. S. Rijkers, R. M. J. Liskamp, C. F. van Nostrum, W. E. Hennink, Bioconjug. Chem. 2009, 20, 2001.
| Crossref | GoogleScholarGoogle Scholar |
[11] H. A. El-Sagheerab, T. Brown, Chem. Soc. Rev. 2010, 39, 1388.
| Crossref | GoogleScholarGoogle Scholar |
[12] R. K. Iha, K. L. Wooley, A. M. Nyström, D. J. Burke, M. J. Kade, C. J. Hawker, Chem. Rev. 2009, 109, 5620.
| Crossref | GoogleScholarGoogle Scholar |
[13] P. L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 2010, 39, 1338.
| Crossref | GoogleScholarGoogle Scholar |
[14] S. Patai, Z. Rappoport, in The Chemistry of Functional Groups: Supplement D2, The Chemistry of Halides, Pseudo-Halides and Azides, 1995, Part 1, p. 2 (Wiley: Chichester).
[15] (a) R. F. Heck, J. Am. Chem. Soc. 1968, 90, 5518.
| Crossref | GoogleScholarGoogle Scholar |
(b) T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581.
| Crossref | GoogleScholarGoogle Scholar |
[16] N. Miyaura, A. Suzuki, J. Chem. Soc., Chem. Commun. 1979, 866.
| Crossref | GoogleScholarGoogle Scholar |
[17] S. Baba, E. Negishi, J. Am. Chem. Soc. 1976, 98, 6729.
| Crossref | GoogleScholarGoogle Scholar |
[18] (a) (a) Reviews on 1,3-dipolar cycloadditions, see: W. Carruthers, in Cycloaddition Reactions in Organic Chemistry 1990, p. 269 (Pergamon: Oxford).
(b) K. V. Gothelf, K. A. Jorgensen, Chem. Rev. 1998, 98, 863.
| Crossref | GoogleScholarGoogle Scholar |
(c) G. L’abbé, Chem. Rev. 1969, 69, 345.
| Crossref | GoogleScholarGoogle Scholar |
(d) C. Spiteri, J. E. Moses, Angew. Chem. Int. Ed. 2010, 49, 31.
[19] (a) A. Štimac, I. Leban, J. Kobe, Synlett 1999, 1069.
| Crossref | GoogleScholarGoogle Scholar |
(b) N. Joubert, R. F. Schinazi, L. A. Agrofoglio, Tetrahedron 2005, 61, 11744.
| Crossref | GoogleScholarGoogle Scholar |
[20] J. E. Hein, J. C. Tripp, L. Krasnova, K. B. Sharpless, V. V. Fokin, Angew. Chem. Int. Ed. 2009, 48, 8018.
| Crossref | GoogleScholarGoogle Scholar |
[21] J. Huang, S. J. F. Macdonald, J. P. A. Harrity, Chem. Commun. 2009, 436.
| Crossref | GoogleScholarGoogle Scholar |
[22] B. H. M. Kuijpers, G. C. T. Dijkmans, S. Groothuys, P. J. L. M. Quaedflieg, R. H. Blaauw, F. L. van Delft, F. P. J. T. Rutjes, Synlett 2005, 3059.
[23] J. Garcia-Álvarez, J. Díez, J. Gimeno, Green Chem. 2010, 12, 2127.
| Crossref | GoogleScholarGoogle Scholar |
[24] B. R. Buckley, S. E. Dann, H. Heaney, Chem. – Eur. J. 2010, 16, 6278.
| Crossref | GoogleScholarGoogle Scholar |
[25] P. Dinér, T. Andersson, J. Kjellén, K. Elbing, S. Hohmannb, M. Grøtli, New J. Chem. 2009, 33, 1010.
| Crossref | GoogleScholarGoogle Scholar |
[26] Y. M. Wu, J. Deng, Y. Li, Q. Y. Chen, Synthesis 2005, 1314.
| Crossref | GoogleScholarGoogle Scholar |
[27] L. Li, G. Zhang, A. Zhu, L. Zhang, J. Org. Chem. 2008, 73, 3630.
| Crossref | GoogleScholarGoogle Scholar |
[28] V. Malnuit, M. Duca, A. Manout, K. Bougrin, R. Benhida, Synlett 2009, 2123.
[29] N. Joubert, R. F. Schinazi, L. A. Agrofoglio, Tetrahedron 2005, 61, 11744.
| Crossref | GoogleScholarGoogle Scholar |
[30] V. D. Bock, R. Perciaccante, T. P. Jansen, H. Hiemstra, J. H. van Maarseveen, Org. Lett. 2006, 8, 919.
| Crossref | GoogleScholarGoogle Scholar |
[31] J. March, Advanced Organic Chemistry, 4th edn 2000 (Wiley-Interscience: New York, NY).
[32] A. K. Mohanakrishnan, C. Prakash, N. Ramesh, Tetrahedron 2008, 64, 3242.
[33] L. Lista, A. Pezzella, A. Napolitano, M. d’Ischia, Tetrahedron 2008, 64, 234.
| Crossref | GoogleScholarGoogle Scholar |
[34] J. Iskra, S. Stavber, M. Zupan, Tetrahedron Lett. 2008, 49, 893.
| Crossref | GoogleScholarGoogle Scholar |
[35] K. Rajender Reddy, M. Venkateshwar, C. Uma Maheswari, P. Santhosh Kumar, Tetrahedron Lett. 2010, 51, 2170.
| Crossref | GoogleScholarGoogle Scholar |
[36] R. Carrington, G. Shaw, D. V. Wilson, J. Chem. Soc. 1965, 6864.
| Crossref | GoogleScholarGoogle Scholar |
[37] (a) G. Zhang, L. Shi, Q. Liu, J. Wang, L. Li, X. Liu, Tetrahedron 2007, 63, 9705.
| Crossref | GoogleScholarGoogle Scholar |
(b) P. B. Alper, S. Huang, C. Wong, Tetrahedron Lett. 1996, 37, 6029.
| Crossref | GoogleScholarGoogle Scholar |
[38] F. Wang, Z. Yang, H. Jin, L. Zhang, L. Zhang, Tetrahedron Asymmetry 2007, 18, 2139.
| Crossref | GoogleScholarGoogle Scholar |
