CiteScore: 2.1     h-index: 21

Document Type : Original Research Article

Authors

1 Iqra Pharmaceuticals, Nutanhat, Burdwan, West Bengal-713147, India

2 Diu College, DHES, Diu (U.T)- 362520, India

3 Om College of Science, Junagadh-Gujrat-362310, India

10.33945/SAMI/AJGC.2019.4.4

Abstract

This work describes the synthesis of complex small molecules spirooxindoles using imidazole as an efficient organocatalyst. The three components coupling reactions of isatin, malononitrile and enolizable 4-hydroxycoumarin were performed in water as a green solvent. The reaction is done with imidazole an amphoteric organocatalyst to construct spiro-molecules in high yields. The significant features of this protocol are neutral reaction condition, readily available low cost catalyst, metal free, strong acid/base free, and reusable reaction medium with no column chromatography separation. This methodology is useful for the easy access of structurally complex, highly functionalized spirooxindole molecules with important medicinal chemistry applications.

Graphical Abstract

Imidazole mediated synthesis of spirooxindoles in water using isatin as a privileged scaffold

Keywords

Main Subjects

[1]. Zhu J., Bienayme H. Multicomponent Reactions; Wiley-VCH: Weinheim Germany, 2005
[2]. Zhu J., Wang Q., Wang M. Multicomponent Reactions in Organic Synthesis; Wiley-VCH: Weinheim Germany, 2014
[3]. Jung G. Combinatorial Chemistry: Synthesis, Analysis, Screening; Wiley-VCH: Weinheim Germany, 2008; p 125
[4]. Trabocchi A. Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology; Wiley: Hoboken New Jersey, 2013; p 29
[5]. Zarganes-Tzitzikas T., Dömling A. Org. Chem. Front., 2014, 1:834
[6]. Weber L. Cur. Med. Chem., 2002, 9:2085
[7]. Sunderhaus J.D., Martin S.F. Chemistry, 2009, 15:1300
[8]. Kaur M., Singh M., Chadha N., Silakari O. Eur. J. Med. Chem., 2016, 123:858
[9]. Ye N., Chen H., Wold E.A., Shi P.Y., Zhou J. ACS Infect. Dis., 2016, 2:382
[10]. Yu B., Yu D.Q., Liu H.M. Eur. J. Med. Chem., 2015, 97:673
[11]. Sun Y., Liu J., Jiang X., Sun T., Liu L., Zhang X., Ding S., Li J., Zhuang Y., Wang Y., Wang R. Sci. Rep., 2015, 5:13699
[12]. Baran P.S., Richter J.M. J. Am. Chem. Soc., 2005, 127:15394
[13]. Edmondson S., Danishefsky S.J., Sepp-Lorenzino L., Rosen N. J. Am. Chem. Soc., 1999, 121:2147
[14]. Saraswat P., Jeyabalan G., Hassan M.Z., Rahman M.U., Nyola N.K. Synth. Commun., 2016, 46:1643
[15]. Panda S.S., Jones R.A., Bachawala P., Mohapatra P.P. Mini Rev. Med. Chem., 2017, 17:1515
[16]. Zheng Y.J., Tice C.M. Expert Opin. Drug Discov. 2016, 11:831
[17]. Wang S., Sun W., Zhao Y., McEachern D., Meaux I., Barriere C., Stuckey J.A., Meagher J.L., Bai L., Liu L., Hoffman-Luca C.G., Lu J., Shangary S., Yu S., Bernard D., Aguilar A., Dos-Santos O., Besret L., Guerif S., Pannier P., Gorge-Bernat D., Debussche L. Cancer Res., 2014, 74:5855
[18]. Singh G.S., Desta Z.Y. Chem. Rev., 2012, 112:6104
[19]. Pal S., Khan M.N., Karamthulla S., Choudhury L.H. Tetrahedron Lett., 2015, 56:359
[20]. Pal S., Khan M.N., Karamthulla S., Abbas S.J., Choudhury L.H. Tetrahedron Lett., 2013, 54:5434
[21]. Karamthulla S., Pal S., Khan M.N., Choudhury L.H. RSC Adv., 2013, 13:15576
[22]. Molla A., Ranjan S., Rao M.S., Dar A.H., Shyam M., Jayaprakash V., Hussain S. ChemistrySelect, 2018, 3:8669
[23]. Sadat-Ebrahimi S.E., Haghayegh-Zavareh S.M., Bahadorikhalili S., Yahya-Meymandi A., Mahdavi M., Saeedi M. Synth. Commun., 2017, 47:2324
[24]. Safaei-Ghomi J., Nazemzadeh S. H., Shahbazi-Alavi H. Catal. Commun., 2016, 86:14
[25]. Singh N.G., Lily M., Devi S.P., Rahman N., Ahmed A., Chandra A.K., Nongkhlaw R. Green Chem., 2016, 18:4216
[26]. Brahmachari G., Banerjee B. Asian J. Org. Chem., 2016, 5:271
[27]. Baghernejad M., Khodabakhshi S., Tajik S. New J. Chem., 2016, 40:2704
[28]. Molla A., Hussain S. RSC Adv., 2016, 6:5491
[29]. Nasseri M.A., Kamali F., Zakerinasab B. RSC Adv., 2015, 5:26517
[30]. He T., Zeng Q.Q., Yang D.C., He Y.H., Guan Z. RSC Adv., 2015, 5:37843
[31]. Khazaei A., Zolfigol M. A., Karimitabar F., Nikokar I., Moosavi-Zarec A. R. RSC Adv., 2015, 5:71402
[32]. Satasia S.P., Kalaria P.N., Avalani J.R., Raval D.K. Tetrahedron, 2014, 70:5763
[33]. Thakur A., Tripathi M., Rajesh U.C., Rawat D.S. RSC Adv., 2013, 3:18142
[34]. Saluja P., Aggarwal K., Khurana J.M. Synth. Commun., 2013, 43:3239
[35]. Hasaninejad A., Golzar N., Beyrati M., Zare A., Doroodmand M.M. J. Mol. Catal. A Chem., 2013, 372:137
[36]. Nasseri M.A., Sadeghzadeh S.M. J. Iran Chem. Soc., 2013, 10:1047
[37]. Guo R.Y., An Z.M., Mo L.P., Wang R.Z., Liu H.X., Wang S.X., Zhang Z.H. ACS Comb. Sci.,2013,15:557
[38]. Mohammadi Ziarani G., Hosseini Mohtasham N., Lashgari N., Badiei A., Amanlou M., Bazlc R. J. Nanostruct., 2013, 2:489
[39]. Safaei H.R., Shekouhy M., Rahmanpur S., Shirinfeshan A. Green Chem., 2012,14:1696
[40]. Hamadi H., Gholami M., Khoobi M. International J. Heterocyclic Chem., 2011, 1:1
[41]. Karimi A.R., Sedaghatpour F. Synthesis, 2010,10:1731
[42]. Baer D.R., Munusamy P., Thrall B.D. Biointerphases, 2016, 11:04B401
[43]. Karakoti A.S., Munusamy P., Hostetler K., Kodali V., Kuchibhatla S., Orr G., Pounds J.G., Teeguarden J.G., Thrall B.D., Baer D.R. Surf. Interface Anal., 2012, 44:882
[44]. Baer D.R. Front. Chem., 2018, 6:145
[45]. Bertelsen S., Jorgensen K.A. Chem. Soc. Rev., 2009, 38:2178
[46]. Dalpozzo R., Bartoli G., Bencivenni G., Chem. Soc. Rev., 2012, 41:7247
[47]. Qin Y., Zhu L., Luo S. Chem. Rev., 2017, 117:9433
[48]. Verma S.K., Acharya B.N., Kaushik M.P. Org. Lett., 2010, 12:4232
[49]. Huang X.G., Liu J., Ren J., Wang T., Chen W., Zeng B.B. Tetrahedron., 2011, 67:6202
[50]. Guan X.Y., Shi M. Org. Biomol. Chem., 2008, 6:3616
[51]. Khan M.N., Pal S., Karamthulla S., Choudhury L.H. RSC Adv., 2013, 4:3732
[52]. Huang C.N., Kuo P.Y., Lin C.H., Yang D.Y. Tetrahedron, 2007, 63:10025