h-index: 7     i10-index: 6

Document Type : Original Research Article

Authors

1 Department of Chemistry, Damghan University, Damghan, Semnan, Iran

2 Department of Chemistry, Faculty of Science, Shahrekord University, Shahrekord, Iran

10.48309/ejst.2024.444677.1133

Abstract

The biological activities and therapeutic qualities of indoles as well as their derivatives have garnered significant attention. I n this study, the solid acidic organocatalyst (sulfanilic acid) was examined for the synthesis of derivatives of bis(indolyl)methanes (BIMs) at ambient temperature and in water and ethanol as solvent. BIMs was prepared and characterized by appearance, TLC, FT-IR, and melting point and were further supported by CHNS analysis. The approach has a lot of advantages, including a clean reaction, operational simplicity, a simple experimental work-up process, waste minimization, non-toxicity, quicker reaction times, and high yields of the compounds.

Keywords

Main Subjects

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[1] Banari H., Kiyani H., Pourali A.R., Bisindolization reaction employing phthalimide-N-sulfonic acid as an efficient catalyst, Current Organocatalysis, 2020, 7:124 [Crossref], [Google Scholar], [Publisher]‎
[2] Yaghoubi A., Dekamin M.G., Arefi E., Karimi B., Propylsulfonic acid-anchored isocyanurate-based periodic mesoporous organosilica (PMO-ICS-Pr-SO3H):A new and highly efficient recoverable nanoporous catalyst for the one-pot synthesis of bis (indolyl) methane derivatives, Journal of Colloid and Interface Science, 2017, 505:956 [Crossref], [Google Scholar], [Publisher]‎
[3] Kalla R.M.N., Hong S.C., Kim I., Synthesis of bis (indolyl) methanes using hyper-cross-linked polyaromatic spheres decorated with bromomethyl groups as efficient and recyclable catalysts, ACS Omega, 2018 3:2242[Crossref], [Google Scholar], [Publisher]‎
[4] Mohapatra S.S., Wilson Z.E., Roy S., Ley S.V., Utilization of flow chemistry in catalysis: New avenues for the selective synthesis of Bis (indolyl) methanes, Tetrahedron, 2017, 73:1812 [Crossref], [Google Scholar], [Publisher]‎
[5] Lee S.O., Choi J., Kook S.,  Lee S.Y., Lewis acid-catalyzed double addition of indoles to ketones:synthesis of bis (indolyl) methanes with all-carbon quaternary centers, Organic & Biomolecular Chemistry, 2020, 18:9060 [Crossref], [Google Scholar], [Publisher]‎
[6] Athavale R., Gardi S., Choudhary F., Patil D., Chandan N., More P., Novel acidic ionic liquid [BEMIM][HSO4]:A highly efficient and recyclable catalyst for the synthesis of bis-indolyl methane derivatives,  Applied Catalysis A:General, 2024, 669:119505 [Crossref], [Google Scholar], [Publisher]‎
[7] Galathri E.M., Kuczmera T.J., Nachtsheim B.J., Kokotos C.G., Organocatalytic Friedel–Crafts arylation of aldehydes with indoles utilizing N-heterocyclic iod (az) olium salts as halogen-bonding catalysts, Green Chemistry, 2024, 26:825 [Crossref], [Google Scholar], [Publisher]‎
[8]  Wai Chia P., Soon Lim B., Chen Tan Kh., Siong Julius Yong F., Kan S.Y, Water extract of onion peel for the synthesis of bisindolylmethanes, Journal of King Saud University–Science, 2019, 31:642. [Crossref], [Google Scholar], [Publisher]‎
[9] Ali R., Ahamad M.Z., Singh S., Haq W., Regioselective synthesis of symmetrical and unsymmetrical bis (heteroaryl) methane (BHM)‐containing amino acids, European Journal of Organic Chemistry, 2019, 2019:1820 [Crossref], [Google Scholar], [Publisher]‎
[10]  Kumbhar V., Raskar R., Chafle R., Nikam V., Kumbhar A., Pawar R., Chaskar M., Gugale G. Khairnar B., ProHSO4:An efficient catalyst for solvent-free synthesis of bis (indolyl) methanes and their in silico screening for potential biological activity, Results in Chemistry, 2023, 6:101023 [Crossref], [Google Scholar], [Publisher]‎
[11] Nguyen N.K., Ha M.T., Bui H.Y., Trinh Q.T., Tran B.N., Hung T.Q., Dang T.T., Vu X.H., Magnetically recyclable CuFe2O4 catalyst for efficient synthesis of bis (indolyl) methanes using indoles and alcohols under mild condition, Catalysis Communications, 2021,  149:106240 [Crossref], [Google Scholar], [Publisher]‎
[12]  Ghodrati K., Hosseini S.H., Mosaedi R., Karami C., Maleki F., Farrokhi A., Hamidi Z., Convenient, efficient, and green method for synthesis of bis (indolyl) methanes with nano SIO 2 under ultrasonic irradiation, International Nano Letters, 2013, 3:1 [Crossref], [Google Scholar], [Publisher]‎
[13] Selvakumar K., Shanmugaprabha T., Annapoorani R., Sami P., One-pot three-component synthesis of bis (indolyl) methanes under solvent-free condition using heteropoly-11-tungsto-1-vanadophosphoric acid supported on natural clay as catalyst,  Synthetic Communications, 2017, 47:913 [Crossref], [Google Scholar], [Publisher]‎
[14] Kasar S.B.,  Thopate S.R., Synthesis of bis (indolyl) methanes using naturally occurring, biodegradable itaconic acid as a green and reusable catalyst,  Current Organic Synthesis, 2018, 15:110 [Crossref], [Google Scholar], [Publisher]‎
[15] Mhaldar S.N., Mandrekar K.S., Gawde M.K., Shet R.V.,  Tilve S.G., Solventless mechanosynthesis of bis (indolyl) methanes, Synthetic Communications, 2019,  49:94 [Crossref], [Google Scholar], [Publisher]‎
[16] Khatab T.K., Abdelghany A.M.,  Soliman H.A., V2O5/SiO2 as a heterogeneous catalyst in the synthesis of bis (indolyl) methanes under solvent free condition,  Silicon, 2018,  10, 703 [Crossref], [Google Scholar], [Publisher]‎
[17] Hasaninejad A., Zare A., Sharghi H., Khalifeh R., Zare A.R.M., PCl5 as a mild and efficient catalyst for the synthesis of bis (indolyl) methanes and di-bis (indolyl) methanes, Bulletin of the Chemical Society of Ethiopia, 2008, 22 [Crossref], [Google Scholar], [Publisher]‎
[18] Mallik  A.K., Pal R., Guha  C.,  Mallik H., A convenient, eco-friendly, and efficient method for synthesis of bis (3-indolyl) methanes “on-water”,Green Chemistry Letters and Reviews, 2012, 5:321 [Crossref], [Google Scholar], [Publisher]‎
[19] Dhumaskar K.L., Tilve S.G., Synthesis of bis (indolyl) methanes under catalyst-free and solvent-free conditions, Green Chemistry Letters and Reviews, 2012, 5:353 [Crossref], [Google Scholar], [Publisher]‎
[20] Kidwai M., Chauhan  R., Bhatnagar D., Nafion-H® catalyzed efficient condensation of indoles with aromatic aldehydes in PEG-water solvent system:A green approach,  Arabian Journal of Chemistry, 2016, 9, 2004 [Crossref], [Google Scholar], [Publisher]‎