Green and Efficient Synthesis of 3-Pyrazolyl Indoles in Water

doi:10.1007/s40242-019-0011-8

Chemical Research in Chinese Universities ›› 2020, Vol. 36 ›› Issue (5): 847-852.doi: 10.1007/s40242-019-0011-8

• Articles • Previous Articles Next Articles

Green and Efficient Synthesis of 3-Pyrazolyl Indoles in Water

ZHAO Yanhui¹, YU Haifeng¹, LIAO Peiqiu², WANG Wenju¹

1. College of Chemistry, Baicheng Normal University, Baicheng 137000, P. R. China;
2. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University, Changchun 130024, P. R. China

Received:2019-10-20 Revised:2019-12-11 Online:2020-10-01 Published:2020-10-01
Contact: YU Haifeng, WANG Wenju E-mail:yuhf68105@sina.com;wangwj3309@163.com
Supported by:
Supported by the National Natural Science Foundation of China(No.20902010) and the Foundation of Science and Technology Research Projects of the 13th Five-year Plan of Jilin Provincial Department of Education, China(No.2016037).

Abstract

Abstract: A green and efficient synthesis of 3-pyrazolyl indoles was developed by the cyclocondensation reaction of β-ethylthio-β-indolyl-α,β-unsaturated ketones with semicarbazide hydrochloride as hydrazine equivalent in the presence of 3 equiv. of PEG-400(1a/PEG mole ratio of 1:3) in reflux water. This procedure did not require toxic hydrazine and product purification, eliminating the use of toxic liquid chemicals.

Key words: 3-Pyrazolyl indole, Green synthesis, Semicarbazide hydrochloride, Polyethylene glycol, Hydrazine equivalent

ZHAO Yanhui, YU Haifeng, LIAO Peiqiu, WANG Wenju. Green and Efficient Synthesis of 3-Pyrazolyl Indoles in Water[J]. Chemical Research in Chinese Universities, 2020, 36(5): 847-852.

References 44

[1]	Singh S., Chauhan P., Ravi M., Yadav P. P., New J. Chem., 2018, 42, 6617
[2]	Anand D., Yadav P. K., Patel O. P. S., Parmar N., Maurya R. K., Vishwakarma P., Raju K. S. R., Taneja I., Wahajuddin M., Kar S., Yadav P. P., J. Med. Chem., 2017, 60(3), 1041
[3]	Gmeiner P., Huebner H., Abu S. K. A., Heterocycles, 2003, 60(6), 1339
[4]	Zhang Y. M., Wang R., Shi Z. J., Zhang W., Synthesis, 2011, 11, 1711
[5]	Esvan Y. J., Giraud F., Pereira E., Suchaud V., Nauton L., Théry V., Dezhenkova L. G., Kaluzhny D. N., Mazov V. N., Shtil A. A., Anizon F., Moreau P., Bioorgan. Med. Chem., 2016, 24(14), 3116
[6]	Sechi M., Innocenti A., Pala N., Rogolino D., Carcelli M., Scozzafava A., Supuran C. T., Bioorgan. Med. Chem. Lett., 2012, 22(18), 5801
[7]	Cadoni R., Pala N., Lomelino C., Mahon B. P., McKenna R., Dallocchio R., Dessì A., Carcelli M., Rogolino D., Sanna V., Rassu M., Iaccarino C., Vullo D., Supuran C. T., Sechi M., ACS Med. Chem. Lett., 2017, 8(9), 941
[8]	Rao R. M., Reddy G. N., Sreeramulu J., Der. Pharma. Chemica, 2011, 3(5), 301
[9]	Somappa S. B., Biradar J. S., Rajesab P., Rahber S., Sundar M., Monatsh. Chem., 2015, 146(12), 2067
[10]	El-Mekabaty A., Etman H. A., Mosbah A., J. Heterocyclic Chem., 2016, 53, 894
[11]	Ummadi N., Gundala S., Venkatapuram P., Adivireddy P., Med. Chem. Res., 2017, 26, 1574
[12]	Gupton J. T., Telang N., Gazzo D. F., Barelli P. J., Lescalleet K. E., Fagan J. W., Mills B. J., Finzel K. L., Kanters R. P. F., Crocker K. R., Dudek S. T., Lariviere C. M., Smith S. Q., Keertikar K. M., Tetrahedron, 2013, 69(29), 5829
[13]	El-Mekabaty A., Mesbah A., Fadda A. A., J. Heterocyclic Chem., 2017, 54(2), 916
[14]	Conchon E., Aboab B., Golsteyn R. M., Cruzalegui F., Edmonds T., Léonce S., Pfeiffer B., Prudhomme M., Eur. J. Med. Chem., 2006, 41(12), 1470
[15]	Wen J. C., Bao Y., Niu Q., Yang J. Y., Fan Y. B., Li J. H., Jing Y. K., Zhao L. X., Liu D., Eur. J. Med. Chem., 2016, 109, 350
[16]	Cocconcelli G., Diodato E., Caricasole A., Gaviraghi G., Genesio E., Ghiron C., Magnoni L., Pecchioli E., Plazzi P. V., Terstappen G. C., Bioorgan. Med. Chem., 2008, 16(4), 2043
[17]	Krasavin M., Konstantinov I. O., Lett. Org. Chem., 2008, 5(7), 594
[18]	Diana P., Carbone A., Barraja P., Martorana A., Gia O., DallaVia L., Cirrincione, G., Bioorgan. Med. Chem. Lett., 2007, 17(22), 6134
[19]	Abo-salem H. M., Ahmed K. M., El-Hallouty S., El-sawy E. R., Mandour A. H., Int. J. Pharm. Pharm. Sci., 2016,8(12), 113
[20]	Abu Safieh K. A., El-Abadelah M. M., Sabri S. S., Abu Zarga M. H., Voelter W., Mössmer C. M., J. Heterocyclic Chem., 2001, 38(3), 623
[21]	Gmeiner P., Hübner H., Abu Safieh K. A., Fasfous I. I., El-Abadelah M. M., Sabri S. S., Voelter W., Heterocycles, 2003, 60(6), 1339
[22]	Reddy C. R., Vijaykumar J. R., Synthesis, 2013, 45, 830
[23]	Usachev B. I., Obydennov D. I., Kodess M. I., Sosnovskikh V. Y., Tetrahedron Lett., 2009, 50, 4446
[24]	Kumari S., Shekharb A., Pathak D. D., New J. Chem., 2016, 40, 5053
[25]	Usachev B. I., Obydennov D. L., Sosnovskikh V. Y., J. Fluorine Chem., 2012, 135, 278
[26]	Kumari S., Shekhar A., Pathak D. D., New J. Chem., 2016, 40, 5053
[27]	Hazra S., Deb M., Elias A. J., Green Chem., 2017, 19, 5548
[28]	Wu C., Lu L. H., Peng A. Z., Jia G. K., Peng C., Cao Z., Tang Z., He W. M., Xu X., Green Chem., 2018, 20, 3683
[29]	Pakamorė I., Rousseau J., Rousseau C., Monflier E., Szilágyi P. Á., Green Chem., 2018, 20, 5292
[30]	Xie L. Y., Peng S., Liu F., Liu Y. F., Sun M., Tang Z. L., Jiang S., Cao Z., He W. M., ACS Sustainable Chem. Eng., 2019, 77, 7193
[31]	Zhang Q. Q., Ge Y. C., Yang C. J., Zhang B. G., Deng K. J., Green Chem., 2019, 21, 5019
[32]	Dong D. W., Ouyang Y., Yu H. F., Liu Q., Liu J., Wang M., Zhu J., J. Org. Chem., 2005, 70, 4535
[33]	Yu H. F., Liao P. Q., Chemistry, 2013, 5, 435
[34]	Yu H. F., Liao P. Q., Tetrahedron Lett., 2016, 57, 2868
[35]	Qi F., Yu H. F., Wang Y. N., Lv Y., Li Y. X., Han L., Wang R., Feng X. N., Synth. Commun., 2017, 47(23), 2220
[36]	Yu H. F., Yu Z. K., Angew. Chem. Int. Ed., 2009, 48, 2929
[37]	Yu H. F., Li T. C., Liao P. Q., Synthesis, 2012, 44, 3743
[38]	Wang W. J., Yu, H. F., Synth. Commun., 2019, 49(3), 377
[39]	Marković V., Joksović M. D., Green Chem., 2015, 17, 842
[40]	Dickerson T. J., Reed N. N., Janda K. D., Chem. Rev., 2002, 102, 3325
[41]	Burley G. A., Davies D. L., Griffith G. A., Lee M., Singh K., J. Org. Chem., 2010, 75, 980
[42]	Kidwai M., Bhatnagar D., Tetrahedron Lett., 2010, 51, 2700
[43]	Jawale D. V., Pratap U. R., Bhosale M. R., Mane R. A., J. Heterocyclic Chem., 2016, 53(5), 1626
[44]	Brückner R.; Ed. Hamata M., Organic Mechanisms:Reactions, Stereochemistry and Synthesis, 3rd Edn., Springer, Berlin, 2010, 344

Green and Efficient Synthesis of 3-Pyrazolyl Indoles in Water

Knowledge

Abstract

Cite this article

share this article

References 44

Related Articles 7

Recommended Articles

Metrics

Comments

[1]	XIONG Jin'en, LI Shuang, LI Yi, CHEN Yingli, LIU Yu, GAN Junlan, JU Jiahui, XIAN Yaoling, XIONG Xiaohui. Fluorescent Aptamer-Polyethylene Glycol Functionalized Graphene Oxide Biosensor for Profenofos Detection in Food [J]. Chemical Research in Chinese Universities, 2020, 36(5): 787-794.
[2]	HUANG Sa, HAN Qinghe, WANG Lei, GONG Tingting, YUAN Qinghai. One-pot Synthesis of PEGylated Gd-based Nanoparticles as High-performance and Biocompatibility Contrast Agents for T ₁-Weighted Magnetic Resonance Imaging In vivo [J]. Chemical Research in Chinese Universities, 2019, 35(3): 537-541.
[3]	LU Xueting, FENG Wei, WANG Honglei, HU Qianqian, GUAN Shuang, GUO Peipei. Bentonite Reinforced Tough Composite Hydrogels as Potential Artificial Articular Cartilage [J]. Chemical Research in Chinese Universities, 2018, 34(6): 1028-1034.
[4]	JIANG Yuhang, LI Yao, WANG Xuesong, PIAO Linglan, SHI Zuosen, CUI Zhanchen. Fabrication of New Transparent and Hydrophilic Hybrid Anti-fog Coating from Silane Coupler Modified by Polyethylene Glycols [J]. Chemical Research in Chinese Universities, 2017, 33(1): 150-154.
[5]	ZHANG Yinan, JIANG Dong, HE Zhi, YU Yunwu, ZHANG Haibo, JIANG Zhenhua. Hydrothermal Synthesis of PEG-capped ZnS：Mn²⁺ Quantum Dots Nanocomposites [J]. Chemical Research in Chinese Universities, 2014, 30(1): 176-180.
[6]	NAWAZ Faisal, WANG Liang, ZHU Long-feng, MENG Xiang-ju, XIAO Feng-Shou. Ascorbic Acid Assisted Green Route for Synthesis of Water Dispersible Carbon Dots [J]. Chemical Research in Chinese Universities, 2013, 29(3): 401-403.
[7]	JIN Gu*, YAO Qi-zhi, DONG Li-quan and MA Feng. PEG-grafted PVA Membrane and Its Blood Compatibility [J]. Chemical Research in Chinese Universities, 2011, 27(6): 1078-1082.