Phenylboronic Acid/CuSO4 as an Efficient Catalyst for the Synthesis of 1,4-Disubstituted-1,2,3-Triazoles from Terminal Acetylenes and Alkyl Azides

Authors

  • Heraclio López-Ruiz Área Académica de Química (AAQ), Universidad Autónoma del Estado de Hidalgo (UAEH), Ciudad Universitaria, Carretera Pachuca-Tulancingo Km 4.5, C.P 42184 Mineral de la Reforma, Hidalgo, México.

DOI:

https://doi.org/10.29356/jmcs.v59i2.26

Keywords:

Triazoles, phenylboronic acid, CuSO4, Microwave irradiation

Abstract

The synthesis of 1,4-disubstituted-1,2,3-triazoles from alkyl azides and terminal alkynes at room temperature and under microwave heating was attained using Cu(I), generated in-situ from copper(II) sulfate and phenylboronic acid, as catalyst. Twelve new triazoles were obtained in moderate to good yields (53-98%), and the products were obtained by crystallization from the mixture reaction without further purification.

Downloads

Download data is not yet available.

References

For a special issue dedicated to applications of click chemistry see. Ed. by: Finn, M. G. and Fokin, V.V. Chem. Soc. Rev. 2010, 39, 1221-1222.

a) Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952-3015; b) Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51-68; c) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596-2599; d) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 002, 67, 3057-3064.

a) Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radi????, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 1053-1057; b) Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278-308; c) Lee, T.; Cho, M.; Ko, S.-Y.; Youn, H.-J.; Baek, D. J.; Cho, W.-J.; Kang, C.-Y.; Kim, S. J. Med. Chem. 2007, 50, 585-589; d) Maurya, S. K.; Gollapalli, D. R.; Kirubakaran, S.; Zhang, M.; Johnson, C. R.; Benjamin, N. N.; Hedstrom, L.; Cuny, G. D. J. Med. Chem. 2009, 52, 4623-4630; e) Kold, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137; f) Puig-Basagoiti, F.; Qing, M.; Dong, H.; Zhang, B.; Zou, G.; Yuan, Z.; Shi, P.-Y. Antiviral Res. 2009, 83, 71-79; g) Guezguez, R.; Bougrin, K.; Akri, K. E.; Benhida, R. Tetrahedron Lett. 2006, 47, 4807-4811.

Tao, C. Z.; Cui, X.; Li, J.; Liu, A. X.; Liu, L.; Guo, Q. X. Tetrahedron Lett. 2007, 48, 3525-3529.

García, M. A.; Ríos, Z. G.; Gonzáles, J.; Pérez, V. M.; Lara, N.; Fuentes, A.; Gonzáles, C.; Corona, D.; Cuevas-Yañes, E. Lett. Org. Chem. 2011, 8, 701-706.

Mohammed, S.; Padala, A. K.; Dar, B. A.; Singh, B.; Sreedhar, B.; Vishwakarma, R. A.; Bharate, S. B. Tetrahedron. 2012, 68, 8156-8162.

de la Cerda-Pedro, J. E.; Amador-Sánchez, Y. A.; Cortés-Hernández, M.; Pérez-Pérez, J.; Rojas-Lima, S.; López-Ruiz, H. Heterocycles. 2014, 89, 27-41.

Bull, S. D.; Davidson, M. G.; van den Elsen, J. M. H.; Fossey, J. S.; Jenkins, A. T. A.; Jiang, Y –B.; Kubo, Y.; Marken, F.; Sakurai, K.; Zhao, J.; James, T. D. Acc. Chem. Res. 2013, 46, 312-326.

Chen, T.; Huang, Q.; Luo, Y.; Hu, Y.; Lu, W. Tetrahedron Lett. 2013, 54, 1401-1404.

Sawant, S. D.; Hudwekar, A. D.; Kumar, K. A. A.; Venkateswarlu, V.; Singh, P. P.; Vishwakarma, R. A. Tetrahedron Lett. 2014, 55, 811-814.

a) Mukherjee, N.; Ahammed, S.; Bhadra, S.; Ranu, B. C. Green Chem. 2013, 15, 389-397; b) Kaboudin, B.; Abedi, Y.; Yokomatsu, T. Org. Biomol. Chem. 2012, 10, 4543-4548.

López-Ruiz, H.; de la Cerda-Pedro, J. E.; Rojas-Lima, S.; Pérez-Pérez, I.; Rodríguez-Sánchez, B. V.; Santillán, R.; Coreño, O. Arkivoc. 2013, iii, 139-164.

Suarez A. An. Quími. 2012, 108, 306-313.

Angell, Y.; Burgess, K. Angew. Chem. Int. Ed. 2007, 46, 3649-3651.

González, J.; Pérez, V. M.; Jiménez, D. O.; López-Valdez, G.; Corona, D.; Cuevas-Yañez, E. Tetrahedron Lett. 2011, 52, 3514- 3517.

X-ray crystallographic data (excluding structure factors) for the structures in this paper has been deposited with the Cambridge Crystallographic Data Centre as a Supplementary Publication Numbers, CCDC 1007167 No. for 3f, CCDC 1007170 No. for 4, CCDC 1007168 No. for 3h, and CCDC 1007169 No for 3j. Copy of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: [email protected]].

a) Loupy, A. Microwaves in Organic Synthesis. Ed. Wiley-VCH, 2001; b) Hayes, B. L. Microwave synthesis Chemistry at the Speed of light. CEM publishing, 2002; c) Tierney, J.; Lindstrom, P. Microwave Assisted Organic Synthesis. Ed. Blackwll, 2004; d) Kappe, C. O. Angew Chem. Int. Ed. 2004, 43, 6250-6284.

Worrell, B. T.; Malik, J. A.; Fokin, V. V. Science. 2013, 340, 457- 460.

a) King, A. E.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044-5045. b) Srivastava, V. P.; Yadav; D. K.; Yadav, A. K.; Watal, G.; Yadav, L. D. S. Synlett. 2013, 24, 1423-1427. c) Mahanta, A.; Adhikari, P.; Bora, U.; Thakur, A. J. Tetrahedron Lett. 2015, in press.

Downloads

Published

2017-10-12

Issue

Section

Regular Articles