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A Greener, Versatile and Convenient Approach for Catalyst Free Conversion of Pyrazole Aldehydes into Carbonitriles
Corresponding Author(s) : Ragunathan Venkatachalam
Asian Journal of Chemistry,
Vol. 34 No. 11 (2022): Vol 34 Issue 11, 2022
Abstract
A new, efficient and catalyst-free synthetic strategy was developed for ten carbonitriles by the combination of pyrazole aldehydes and hydroxylamine hydrochloride in the presence of green solvent-glycerol. All the synthesized carbonitriles were confirmed from by 1H, 13C NMR and high resolution mass spectroscopies. The proposed synthetic process was simple, effective with high product yields and environmentally benign with mild reaction conditions.
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- A.P. Ingale, S.M. Patil and S.V. Shinde, Tetrahedron Lett., 58, 4845 (2017); https://doi.org/10.1016/j.tetlet.2017.11.032
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D. Murdoch and S. Keam, J. Drugs, 65, 2379 (2005); https://doi.org/10.2165/00003495-200565160-00013
F.F. Fleming, L. Yao, P.C. Ravikumar, L. Funk and B.C. Shook, J. Med. Chem., 53, 7902 (2010); https://doi.org/10.1021/jm100762r
L.H. Jones, N.W. Summerhill, N.A. Swain and J.E. Mills, MedChemComm, 1, 309 (2010); https://doi.org/10.1039/C0MD00135J
M.N. Janakiraman, K.D. Watenpaugh, P.K. Tomich, K.-T. Chong, S.R. Turner, R.A. Tommasi, S. Thaisrivongs and J.W. Strohbach, Bioorg. Med. Chem. Lett., 8, 1237 (1998); https://doi.org/10.1016/S0960-894X(98)00197-8
M.J. Kim, J. Mun and J. Kim, Tetrahedron Lett., 58, 4695 (2017); https://doi.org/10.1016/j.tetlet.2017.11.002
N. Kornblum, R.A. Smiley, R.K. Blackwood and D.C. Iffland, J. Am. Chem. Soc., 77, 6269 (1955); https://doi.org/10.1021/ja01628a064
C.W. Kuo, J.L. Zhu, J.D. Wu, C.M. Chu, C.F. Yao and K.S. Shia, Chem. Commun., 3, 301 (2007); https://doi.org/10.1039/B614061K
T.A. Khan, S. Pernucheralathan, H. Ila and H. Junjappa, Synlett, 2019 (2004); https://doi.org/10.1055/s-2004-830878
F.-E. Chen, Y.-Y. Li, M. Xu and H.-Q. Jia, Synthesis, 1804 (2002); https://doi.org/10.1055/s-2002-33906
N. Iranpoor, H. Firouzabadi, B. Akhlaghinia and N. Nowrouzi, J. Org. Chem., 69, 2562 (2004); https://doi.org/10.1021/jo035238v
N. Mori and H. Togo, Synlett, 1456 (2005); https://doi.org/10.1055/s-2005-868511
N.D. Arote, D.S. Bhalerao and K.G. Akamanchi, Tetrahedron Lett., 48, 3651 (2007); https://doi.org/10.1016/j.tetlet.2007.03.137
H. Sharghi and M.H. Sarvari, Tetrahedron, 58, 10323 (2002); https://doi.org/10.1016/S0040-4020(02)01417-5
M. Carmeli, N. Shefer and S. Rozen, Tetrahedron Lett., 47, 8969 (2006); https://doi.org/10.1016/j.tetlet.2006.10.014
B. Movassagh and S. Shokri, Tetrahedron Lett., 46, 6923 (2005); https://doi.org/10.1016/j.tetlet.2005.08.007
R. Ballini, D. Fiorini and A. Palmieri, Synlett, 1841 (2003); https://doi.org/10.1055/s-2003-41408
B.P. Bandgar and S.S. Makone, Synlett, 262 (2003); https://doi.org/10.1055/s-2003-36779
C.O. Kangani, B.W. Day and D.E. Kelley, Tetrahedron Lett., 48, 5933 (2007); https://doi.org/10.1016/j.tetlet.2007.06.119
V.N. Telvekar and R.A. Rane, Tetrahedron Lett., 48, 6051 (2007); https://doi.org/10.1016/j.tetlet.2007.06.108
K. Mori, K. Yamaguchi, T. Mizugaki, K. Ebitani and K. Kaneda, Chem. Commun., 5, 461 (2001); https://doi.org/10.1039/b009944i
S. Iida and H. Togo, Synlett, 407 (2007); https://doi.org/10.1055/s-2007-967954
F.E. Chen, Y.Y. Kuang, H.F. Dai, L. Lu and M. Huo, Synthesis, 2629 (2003); https://doi.org/10.1055/s-2003-42431
T. Cheewawisuttichai, R.D. Hurst and M. Brichacek, Carbohydr. Res., 502, 108282 (2021); https://doi.org/10.1016/j.carres.2021.108282
J. Xue, Y. Zhou, Y.D. Liu and R. Zhong, Sci. Total Environ., 836, 155592 (2022); https://doi.org/10.1016/j.scitotenv.2022.155592
J. Nandi and N.E. Leadbeater, Org. Biomol. Chem., 17, 9182 (2019); https://doi.org/10.1039/C9OB01918A
W. Zhan, M. Tong, L. Ji, H. Zhang, Z. Ge, X. Wang and R. Li, Chin. Chem. Lett., 30, 973 (2019); https://doi.org/10.1016/j.cclet.2019.01.006
Q. Chen, C. Fang, Z. Shen and M. Li, Electrochem. Commun., 64, 51 (2016); https://doi.org/10.1016/j.elecom.2016.01.011