Document Type: Original Article

Authors

1 Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran

2 Department of Chemistry, Payame Noor University, P.O. Box 19395-3697 Tehran, Iran

Abstract

In this work, multicomponent synthesis of mono and bis spiro-pyrazolopyridines from isatin derivatives, indanedione and 3-methyl-5-aminopyrazole at the presence of 1,4-disulfo-1,4-diazoniabicyclo[2.2.2]octane chloride (DSDABCO) as a novel ionic liquid media is reported. The present methodology offers several advantages such as simple procedure, mild conditions, excellent yields, green media and reduced environmental consequences. The ionic liquid was recovered and reused. The structures of the synthesized spiro-pyrazolopyridine compounds were confirmed by 1H, 13C NMR and FTIR spectral data and elemental analyses.

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[1] Huang S., Lin R., Yu Y., Connolly P.J., Chiu G., Li S., Emanuel S.L., Middleton S.A. Bioorg. Med. Chem. Lett., 2007, 17:1243

[2] Saggar S.A., Sisko J.T., Tucker T.J., Tynebor R.M., Su D.S., Anthony N.J.U. S. Patent Appl.US 2007021442 2007

[3] Zhang P., Pennell A.M.K., Wright J.J.K., Chen W., Leleti M.R., Li Y., Li L., Xu Y. PCT Int. Appl. WO 2007002293 chemocentryx USA

[4] Chiu G., Li S., Connelly P.J., Middleton S.A., Emanuel S.L., Huang S., Lin R., Lu Y. PCT Int. Appl. WO 2006130673 Janssen Pharmaceutica N. V. Belgium.

[5] Feurer A., Luithle J., Wirtz S., Koenig G., Stasch J., Stahl E., Schreiber R., Wunder F., Lang D. PCT Int. Appl. WO 2004009589 Bayer Healthcare AG Germany

[6] Hafed A.A.A., Awad I.M.A., Ahmed R. Collect. Czech. Chem. Commun., 1993, 58:1198

[7] Cappelli A., Nannicini C., Gallelli A., Giuliani G., Valenti S., Mohr G.P., Anzini M., Mennuni L., Ferrari F., Caselli G., Giordani A., Peris W., Makovec F., Giorgi G., Vomero S., J. Med. Chem., 2008, 51:2137

[8] Straub A., Benet-Buckoltz J., Frode R., Kem A., Kohlsdorfer C., Schmitt P., Schwarz T., Siefert H.M., Stasch J.P. Bioorg. Med. Chem., 2002, 10:1711

[9] Stein R.G., Biel J.H., Singh T. J. Med. Chem., 1970, 13:153

[10] Lin R., Connolly P.J., Lu Y., Chiu G., Li S., Yu Y., Huang S., Li M., Emanuel S.L., Middleton S.A, Gruninger R.H., Adams M., Fuentes-Pesquera A.R., Greenberger L.M., Bioorg. Med. Chem. Lett., 2007, 17:4297

[11] de Mello H., Echevarria A., Bemardino A.M., Canto-Cavalheiro M., Leon L.L. J. Med. Chem., 2004, 47:5427

[12] (a) Bernardino A.M.R., de Azevedo A.R., da Silva Pinheiro L.C., Borges J.C., Carvalho V.L., Miranda M.D., de Meneses M.D.F. Med. Chem. Res., 2007, 16:352; (b) Trucker T.J., Sisko J.T., Tynebor R.M., Williams T.M., Felock P.J., Flynn J.A., Lai M.T., Liang Y., McGaughey G., Liu M., Miller M., Moyer G., Munshi V., Perlow-Poehnelt R., Prasad S., Reid J.C., Sanchez R., Torrent M., Vacca J.P., Wan B.L., Yan Y. J. Med. Chem., 2008, 51:6503

[13] Bare T.M., Mclaren C.D., Campbell J.B., Firor J.W., Resch J.F., Walters C.P., Salama A.I., Meiners B.A., Patel J.B. J. Med. Chem., 1998, 32:2561

[14] Ochiai H., Ishida A., Ohtani T., Kusumi K., Kishikawa K., Yamamoto S., Takeda H., Obata T., Makai H., Toda M. Bioorg. Med. Chem., 2004, 12:4089

[15] Bernardino A.M., Rolim da Silva Pinheiro L.C., Rodrigues C.R., Loureiro N.I., Castro H.C., Lanfredi-Rangel A., Sabatini-Lopes J., Borges J.C., Carvalho J.M., Romeiro G.A., Ferreira V.F., Frugulhetti IC.P.P., Vannier-Santosd M.A., Bioorg. Med. Chem., 2006, 14:5765

[16] Hoehn H., Polacek I., Schulze E. J. Med. Chem., 1973, 16:1340

[17] Chu I., Lynch B.M. J. Med. Chem., 1975, 18:161

[18] Kuster G.J.T., Van Berkom L.W.A., Kalmoua M., Van Loevezijn A., Siedregt L.A.J.M., Van Steen B.J., Kruse C.G., Rutjes F.P.J.T., Scheeren H.W. J. Comb. Chem., 2006, 8:85

[19] Tripathy R., Reiboldt A., Messina P.A., Iqbal M., Singh J., Bacon E.R., Angeles T.S., Yang S.X., Album M.S., Robinson C., Chang H., Ruggeri B.A., Mallamo J.P. Bioorg. Med. Chem. Lett., 2006, 16:2158

[20] Amal Raj A., Raghunatan R., Sridevikumaria M.R., Raman N. Bioorg. Med. Chem., 2003, 11:407

[21] Bal T.R., Anand B., Yogeeswari P., Sriram D. Bioorg. Med. Chem. Lett., 2005, 15:4451

[22] Liang T., Neumann C.N., Ritter T. Angew Chem. Int. Ed. Engl., 2013, 52:8214

[23]  Ji S.J., Zhou M.F., Gu D.G., Jiang Z.Q., Loh T.P. Eur. J. Org. Chem., 2004, 2004:1584

[24] Nikpassand M., Pirdelzendeh D. Dyes Pigm., 2016, 130:314

[25] Nikpassand M., Mamaghani M., Tabatabaeian K., Kupaei Abiazi M. Mol. Div., 2009, 13:389

[26] Nikpassand M., Mamaghani M., Tabatabaeian K., Samimi H.A. Synth. Commun., 2010, 40:3552

[27] Nikpassand M., Mamaghani M., Shirini F., Tabatabaeian K. Ultrason. sonochem., 2010, 17:301

[28] Nikpassand M., Zare Fekri L., Shafaati T., Shariati S. Chin. J. Chem., 2012, 30:604

[29] Nikpassand M., Zare Fekri L., Saberi M. Monat. Chem., 2012, 143:289

[30] Zare Fekri L., Mahmoodi N.O., Yahyazadeh A., Nikpassand M. Ultrason. Sonochem., 2012, 19:740

[31] Nikpassand M., Zare Fekri L., Jamshidi N. J. Hetero. Chem., 2015, 52:1580

[32] Nikpassand M., Zare Fekri L., Rahro P.N. Res. Chem. Intermediat., 2019, 45:1707

[33] Hematinezhad K., Nikpassand M., Zare Fekri L. Curr. Org. Synth., 2019, 16:303

[34] Nikpassand M., Zare Fekri L., Nabatzadeh M. Comb. Chem. High Throughput. Screen., 2017, 20:533

[35] Nikpassand M., Zare Fekri L., Sanagou S. Dyes Pigm., 2017, 136:140

[36] Zare Fekri L., Nikpassand M., Pourmirzajani S., Aghazadeh B. RSC Adv., 2018, 8:22313

[37] Nikpassand M., Zare Fekri L., Pourahmad A. J. CO2. Utiliz., 2018, 27:320

[38] Hosseinian A., Zare Fekri L., Monfared A., Vessally E., Nikpassand M. J. Sulfur. Chem., 2018, 39:674

[39] Zare Fekri L., Nikpassand M., Shariati S., Aghazadeh B., Zarkeshvari R., Norouzpour N. J. Orgmet. Chem., 2018, 871:60