One-pot multicomponent click synthesis of some novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes

Keshavarz, Mosadegh

Document Type : Original Research Article

Author

Mosadegh Keshavarz

Department of Gas and Petroleum Yasouj University, Yasouj 75918&ndash;74831, Iran

Abstract

A facile and one-pot multicomponent synthesis of novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes at room temperature is reported. At the first step, in the presence of I2/NaN3 reagents, various alkenes were converted to the corresponding azido iodides and in the next step, the reaction of these compounds with phenylacetylene in the presence of catalytic amount of sodium ascorbate/ CuSO4 afforded regioselective synthesis of 1,4-disubstituted-1H-1,2,3-triazoles in short times and at good to high yields. This green
approach has several advantages such as short reaction times, clean reaction profiles, and simple experimental and workup
procedures. All the products were fully characterized by 1HNMR, 13CNMR, IR and CHN analysis

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

[1] C.D. Hein, X.M. Liu, D. Wang, Pharm. Res., 2008, 25, 2216–2230.

[2] A.D. Moorhouse, S. Haider, M. Gunaratnam, D. Munnur, S. Neidle, J.E. Moses, Mol. BioSyst., 2008, 4,629–642.

[3] A.D. Moorhouse, J.E. Moses, Chem. Med. Chem., 2008, 3, 715-723.

[4] M.V. Gil, M.J. Arevalo, O. Lopez, Synthesis, 2007, 11, 1589–1620.

[5] E.F.V. Scriven, K. Turnbull, Chem. Rev., 1988, 88, 297-300.

[6] A.K. Feldman, B. Colasson, V.V. Fokin, Org. Lett., 2004, 6, 3897-3900.

[7] P. Appukkuttan, W. Dehaen, V.V. Fokin, E. Van der Eycken, Org. Lett., 2004, 6, 4223-4225.

[8] J.A. Demaray, J.E. Thuener, M.N. Dawson, S.J. Sucheck, Bioorg. Med. Chem. Lett., 2008, 18, 4868-4872.

[9] K.A. Dururgkar, R.G. Gonnade, C.V. Ramana, Tetrahedron, 2009, 65, 3974-3978.

[10] K. Odlo, E.A. Høydahl, T.V. Hansen, Tetrahedron Lett., 2007, 48, 2097-3001.

[11] V.S. Sudhir, R.B.N. Baig, S. Chandrasekaran, Eur. J. Org. Chem., 2008, 2423-2427.

[12] D. Kumar, et al., Synlett, 2009, 3, 399-402.

[13] D. Kumar, V.B. Reddy, R.S. Varma, Tetrahedron Lett., 2009, 50, 2065-2068.

[14] C.Z. Tao, X. Cui, J. Li, A.X. Liu, L. Liu, Q.X. Guo, Tetrahedron Lett., 2007, 48, 3525-3528.

[15] J.S. Yadav, B.V.S. Reddy, G.M. Reddy, D.N. Chary, Tetrahedron Lett., 2007, 48, 8773-8775.

[16] G. Kumaraswamy, K. Ankamma, A. Pitchaiah, J. Org. Chem., 2007, 72, 9822-98-26.

[17] B. Sreedhar, P.S. Reddy, V.R. Krishna, Tetrahedron Lett., 2007, 48, 5831-58-34.

[18] J.S. Yadav, B.V.S. Reddy, D.N. Chary, C.H.S. Reddy, Tetrahedron Lett., 2008, 49, 2649-2652.

[19] S. Chittaboina, F. Xie, Q. Wang, Tetrahedron Lett., 2005, 46, 2331-2334. [20] S. Fukuzawa, E. Shimizu, S. Kikuchi, Synlett, 2007, 15, 2436-2438.

[21] N.M. Smith, M.J. Greaves, R. Jewell, M.W.D. Perry, M.J. Stocks, J.P. Stonehouse, Synlett, 2009, 9, 1391-1394.

[22] S. Maisonneuve, J. Xie, Synlett, 2009, 18, 2977-2981.

[23] J. Albadi, M. Keshavarz, F. Shirini, M. Vafaie-nezhad, Catal. Commun., 2012, 27, 17-20.

[24] J. Albadi, M. Keshavarz, M. Abedini, M. Vafaie-nezhad, Chin.Chem. Lett., 2012, 23, 797-800.

[25] S. Saadat, S. Nazari, M. Afshari, M. Keshavarz, Orient. J. Chem., 2015, 31, 1005-1012.

[26] M. Keshavarz, N. Iravani, A. Ghaedi, A. Zarei Ahmady, M. Vafaei-Nezhad, S. Karimi, SpringerPlus., 2013, 2, 64-70.

[27] J. Albadi, M. Keshavarz, Synthetic. Commun., 2013, 43, 2119-2030.

[28] A. Zarei Ahmady, F. Heidarizadeh, M. Keshavarz, Synthetic. commun., 2013, 43, 2100-2109.

[29] M. Keshavarz, B. Karami, A. Zarei Ahmady, A. Ghaedi, H. Vafaei, C.R. Chimie. 2014, 17, 570-576.

[30] M. Keshavarz, R. Badri, Mol. Divers., 2011, 15, 957-962.

[31] A.O. Terent'ev, et al. Synthetic. Commun., 2008, 38, 3797-3809.

Iranian chemical communication

One-pot multicomponent click synthesis of some novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes

References

References

Volume 6, Issue 2, pp. 109-217, Serial No. 19
April 2018
Pages 134-142

One-pot multicomponent click synthesis of some novel 1,4-disubstituted-1H-1,2,3-triazoles from alkenes

References

References

Volume 6, Issue 2, pp. 109-217, Serial No. 19April 2018Pages 134-142

Volume 6, Issue 2, pp. 109-217, Serial No. 19
April 2018
Pages 134-142