Paper
Organic & Biomolecular Chemistry
7
S. F. Wang, Y. Yin, Y. L. Zhang, S. W. Mi, M. Y. Zhao, 19 G. C. Senadi, W. P. Hu, T. Y. Lu, A. M. Garkhedkar,
P. C. Lv, B. Z. Wang and H. L. Zhu, Synthesis, biological
evaluation and 3D-QSAR studies of novel 5-phenyl-1H-
pyrazol cinnamamide derivatives as novel antitubulin
agents, Eur. J. Med. Chem., 2015, 93, 291–299.
(a) A. G. G. Allah, M. M. Hefny, S. A. Salih and M. S. El-
Basiouny, Corrosion Inhibition of Zinc in HCl Solution by
Several Pyrazole Derivatives, Corrosion, 1989, 45, 574–578;
J. K. Vandavasi and J. J. Wang, I -TBHP-catalyzed oxidative
cross-coupling of N-sulfonyl hydrazones and isocyanides to
5-aminopyrazoles, Org. Lett., 2015, 17, 1521–1524.
2
20 C. Ma, P. Wen, J. Li, X. Han, Z. Wu and G. Huang,
Palladium and copper cocatalyzed intermolecular cycliza-
tion reaction: synthesis of 5-aminopyrazole derivatives, Adv.
Synth. Catal., 2016, 358, 1073–1077.
8
(
b) A. G. Allah, M. W. Badawy, H. H. Reham and 21 (a) N. Suryakiran, T. S. Reddy, K. A. Latha, P. Prabhakar,
M. M. Abou-Romia, J. Appl. Electrochem., 1989, 19, 928–932;
K. Yadagiri and Y. Venkateswarlu, An expeditious synthesis
of 3-amino 2H-pyrazoles promoted by methanesulphonic
acid under solvent and solvent free conditions, J. Mol.
Catal. A: Chem., 2006, 258, 371–375; (b) N. Suryakiran,
D. Ramesh and Y. Venkateswarlu, Synthesis of 3-amino
1H-pyrazoles catalyzed by p-toluene sulphonic acid using
polyethylene glycol-400 as an efficient and recyclable
reaction medium, Green Chem. Lett. Rev., 2007, 1, 73–78;
(c) N. Everson, K. Yniguez, L. Loop, H. Lazaro, B. Belanger,
G. Koch, J. Bach, A. Manjunath, R. Schioldager, J. Law,
M. Grabenauer and S. Eagon, Microwave synthesis of 1-aryl-
1H-pyrazole-5-amines, Tetrahedron Lett., 2019, 60, 72–74;
(d) M. Kelada, J. M. D. Walsh, R. W. Devine, P. McArdle and
J. C. Stephens, Synthesis of pyrazolopyrimidinones using a
“one-pot” approach under microwave irradiation, Beilstein
J. Org. Chem., 2018, 14, 1222–1228.
(
c) W. A. Badawy, M. M. Hefny and S. S. El-Egamy, Effect of
Some Organic Amines as Corrosion Inhibitors for Lead in
.3 HCl Solution, Corrosion, 1990, 46, 978–982;
d) M. M. Abou-Romia, H. A. Abd El-Rahaman and
0
(
M
H. A. M. El-Sayed, Effect of Some Organic Amines as
Corrosion Inhibitors for Lead in 0.3 M HCl Solution, Bull.
Electrochem., 1990, 6, 757–982.
K. C. Joshi, V. N. Pathak and U. Garg, Synthesis of some
new fluorine-containing 5-amino-1,3-disubstituted pyra-
zoles and 1H-pyrazolo[3,4-b]pyridines, J. Heterocycl. Chem.,
9
1
979, 16, 1141–1145.
1
0 U. Hanefeld, C. W. Rees and A. J. P. White, J. Chem. Soc.,
Perkin Trans. 1, 1996, 1545.
1 (a) D. S. Dodd, R. L. Martinez, M. Kamau, Z. Ruam,
K. V. Kirk, C. B. Cooper, M. A. Hermsmeier, S. C. Traeger
1
and M. A. Poss, J. Comb. Chem., 2005, 7, 584–588; 22 A. Shaabani, M. T. Nazeri and R. Afshari, 5-Amino-pyra-
(b) D. Villemin and A. Benalloum, A Safe, Simple, One-Pot
zoles: potent reagents in organic and medicinal synthesis,
Preparation of N-Derivatized β-Amino Alcohols and
Mol. Diversity, 2019, 23, 751–807.
Oxazolidinones from Amino Acids, Synth. Commun., 1991, 23 P. Wang, Z. Xie, Z. Hong, J. Tang, O. Wong, C. S. Lee,
2
1, 63–68.
N. Wong and S. Lee, Synthesis, photoluminescence and
electroluminescence of new 1H-pyrazolo[3,4-b]quinoxaline
derivatives, J. Mater. Chem., 2003, 13, 1894–1899.
1
2 H. A. Ioannidou and P. A. Koutentis, The conversion of iso-
thiazoles into pyrazoles using hydrazine, Tetrahedron, 2009,
6
5, 7023–7037.
24 W. Fan, Q. Ye, H. W. Xu, B. Jiang, S. L. Wang and S. Tu,
Novel Double [3 + 2 + 1] Heteroannulation for Forming
Unprecedented Dipyrazolo-Fused 2,6-Naphthyridines, Org.
Lett., 2013, 15, 2258–2261.
1
3 M. C. Bagley, T. Davis, M. C. Dix, C. S. Widdowson and
D. Kipling, Microwave-assisted synthesis of N-pyrazole
ureas and the p38α inhibitor BIRB 796 for study into accel-
erated cell ageing, Org. Biomol. Chem., 2006, 4, 4158– 25 B. Jiang, W. Fan, M. Y. Sun, Q. Ye, S. L. Wang, S. J. Tu and
4
164.
G. Li, Domino Reaction of Arylglyoxals with Pyrazol-5-
amines: Selective Access to Pyrazolo-Fused 1,7-
Naphthyridines, 1,3-Diazocanes, and Pyrroles, J. Org.
Chem., 2014, 79, 5258–5268.
1
1
4 W. N. Su, T. P. Lin, K. M. Cheng, K. C. Sung, S. K. Lin and
F. F. Wong, An efficient one-pot synthesis of N,-(1,3-diphe-
nyl-1H-pyrazol-5-yl) amides, J. Heterocycl. Chem., 2010, 47,
8
31–837.
26 X. J. Tu, W. J. Hao, Q. Ye, S. S. Wang, B. Jiang, G. Li and
S. J. Tu, Four-Component Bicyclization Approaches to
Skeletally Diverse Pyrazolo[3,4-b]pyridine Derivatives,
J. Org. Chem., 2014, 79, 11110–11118.
27 J. Sun, J. K. Qiu, Y. L. Zhu, C. Guo, W. J. Hao, B. Jiang and
S. J. Tu, Metal-Free Iodine-Catalyzed Synthesis of Fully
Substituted Pyrazoles and Its Sulphenylation, J. Org. Chem.,
2015, 80, 8217–8224.
5 B. R. Kim, G. H. Sung, K. E. Ryu, S. G. Lee, H. J. Yoon,
D. S. Shin and Y. J. Yoon, Direct synthesis of pyrazoles
from esters using tertbutoxide-assisted C-(C=O) coupling,
Chem. Commun., 2015, 51, 9201–9204.
1
6 M. Zora and A. Kivrak, Synthesis of pyrazoles via CuI-
mediated electrophilic cyclizations of α, β-alkynic hydra-
zones, J. Org. Chem., 2011, 76, 9379–9390.
1
7 G. J. Reddy, D. Latha and K. S. Rao, A clean and rapid syn- 28 J. Sun, J. K. Qiu, B. Jiang, W. J. Hao, C. Guo and S. J. Tu, I2-
thesis of 5-amino and 5-alkoxycarbonylpyrazoles using
montomorillonite under acid free conditions, Org. Prep.
Proced. Int., 2004, 36, 494–498.
Catalyzed Multicomponent Reactions for Accessing
Densely Functionalized Pyrazolo[1,5-a]pyrimidines and
Their Disulphenylated Derivatives, J. Org. Chem., 2016, 81,
3321–3328.
1
8 J. D. Kirkham, S. J. Edeson, S. Stokes and J. P. Harrity,
Synthesis of ynone trifluoroborates toward functionalized 29 (a) L. J. Chen, J. Zhang, Y. T. Wei, Z. Yang, P. Liu, J. Zhang
pyrazoles, Org. Lett., 2012, 14, 5354–5357.
and B. Dai, NH I/1,10-phenanthroline catalyzed direct sul-
4
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