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DOI: 10.1055/a-2081-9249
Recent Developments in Ultrasound-Promoted Aqueous-Mediated Greener Synthesis of Biologically Vital Indole Derivatives
Financial support was provided by the University Grants Commission, New Delhi (No. F.30-572/2021-BSR) and by the Council of Scientific and Industrial Research, New Delhi, India.
Abstract
The extensive range of uses of N-heterocycles as potent bioactive motifs has attracted researchers to expand newer methods for their efficient synthesis. Particularly, indoles are widely known for their prevalent pharmacological properties. Green chemistry provides various synthetic tools viz. alternative energy resources, nonconventional solvents, nano-catalysts, etc. Modern strategies of using ultrasound as an alternative energy resource in organic synthesis has led to the development of environment friendly and cost-effective techniques. The chemical and mechanical effects of ultrasound waves impart significant enhancement in both stoichiometric and catalytic reactions. The exclusive physicochemical properties of water offer widespread utility for carrying out organic reactions in this medium. The aim of this review article is to provide an inclusive summary of the combined use of ultrasound and aqueous media for the facile synthesis of biologically vital indole derivatives.
1 Introduction
2 Synthesis of Biologically Vital Indoles
2.1 Spirocyclic Indoles
2.2 Non-spiro 3-Substituted Indoles
2.3 Miscellaneous Indole Syntheses
3 Conclusions
Publikationsverlauf
Eingereicht: 05. Januar 2023
Angenommen nach Revision: 20. April 2023
Accepted Manuscript online:
26. April 2023
Artikel online veröffentlicht:
24. Mai 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1a Ferrazzano L, Catani M, Cavazzini A, Martelli G, Corbisiero D, Cantelmi P, Fantoni T, Mattellone A, De Luca C, Felletti S, Cabri W, Tolomelli A. Green Chem. 2022; 24: 975
- 1b Zimmerman JB, Anastas PT, Erythropel HC, Leitner W. Science 2020; 367: 397
- 1c Anastas P, Eghbali N. Chem. Soc. Rev. 2010; 39: 301
- 2a Banerjee B. Ultrason. Sonochem. 2017; 35: 1
- 2b Puri S, Kaur B, Parmar A, Kumar H. Curr. Org. Chem. 2013; 17: 1790
- 2c Baig RB. N, Varma RS. Chem. Soc. Rev. 2012; 41: 1559
- 3a Das P, Bhattacharyya SK, Banerji P, Das NC. Nano-Struct. Nano-Objects 2021; 25: 100641
- 3b Zhao S, Yao C, Zhang Q, Chen G, Yuan Q. Chem. Eng. J. 2019; 374: 68
- 3c Muthupandian AK. Ultrason. Sonochem. 2011; 18: 864
- 4a Pagadala R, Kasi V, Shabalala NG, Jonnalagadda SB. Arabian J. Chem. 2022; 15: 103544
- 4b Patil R, Bhoir P, Deshpande P, Wattamwar T, Shirude M, Chaskar P. Ultrason. Sonochem. 2013; 20: 1327
- 4c Patil R, Bhoir P, Deshpande P, Wattamwar T, Shirude M, Chaskar P. Ultrason. Sonochem. 2013; 20: 1327
- 4d Banerjee B. Aust. J. Chem. 2017; 70: 872
- 4e Banerjee B. Ultrason. Sonochem. 2017; 35: 1
- 4f Kaur N. Synth. Commun. 2018; 48: 1235
- 4g Kaur G, Sharma A, Banerjee B. ChemistrySelect 2018; 3: 5283
- 4h Banerjee B. ChemistrySelect 2019; 4: 2484
- 4i Sharma A, Priya A, Kaur M, Singh A, Kaur G, Banerjee B. Synth. Commun. 2021; 51: 3209
- 5a Gawande MB, Bonifacio VD. B, Luque R, Brancoa PS, Varma RS. Chem. Soc. Rev. 2013; 42: 5522
- 5b Kommi DN, Kumar D, Seth K, Chakraborti AK. Org. Lett. 2013; 15: 1158
- 5c Butler RN, Coyne AG. Chem. Rev. 2010; 110: 6302
- 5d Leadbeater NE. Chem. Commun. 2005; 2881
- 6a Cortes-Clerget M, Yu J, Kincaid JR. A, Walde P, Gallou F, Lipshutz BH. Chem. Sci. 2021; 12: 4237
- 6b Banerjee B. J. Serb. Chem. Soc. 2017; 82: 755
- 7a Zhaoa S, Yao C, Dong Z, Chen G, Yuan Q. Particuology 2020; 48: 88
- 7b Naeimi H, Lahouti S. J. Iran. Chem. Soc. 2018; 15: 2017
- 7c Yusof NS. M, Babgi B, Aksu M, Madhavan J, Muthupandian AK. Ultrason. Sonochem. 2016; 29: 568
- 8a Martins P, Jesus J, Santos S, Raposo LR, Roma-Rodrigues C, Baptista PV, Fernandes AR. Molecules 2015; 20: 16852
- 8b Baumann M, Baxendale IR. Beilstein J. Org. Chem. 2013; 9: 2265
- 8c Dua R, Shrivastava S, Sonwane SK, Srivastava SK. Adv. Biol. Res. 2011; 5: 120
- 8d Baumann M, Baxendale IR, Ley SV, Nikbin N. Beilstein J. Org. Chem. 2011; 7: 442
- 8e Sharom MS, Miles JR. W, Harris CR, McEwen FL. Water Res. 1980; 14: 1095
- 9a Khan S, Quraishi MA. Arabian J. Sci. Eng. 2010; 35: 73
- 9b Behera GB, Behera PK, Mishra BK. J. Surf. Sci. Technol. 2007; 23: 1
- 9c Steingruber E. Indigo and Indigo Colorants. In Ullmann’s Encyclopedia of Industrial Chemistry. Wiley-VCH; Weinheim: 2004
- 9d Darzynkiewicz Z. Methods Cell Biol. 1990; 33: 285
- 10a Demirel N, Haber J, Ivlev SI, Meggers E. Organometallics 2022; 41: 3852
- 10b Lizza JR, Bremerich M, McCabe SR, Wipf P. Org. Lett. 2018; 20: 6760
- 10c Li QZ, Zeng R, Fan Y, Liu YQ, Qi T, Zhang X, Li JL. Angew. Chem. 2022; 61: e202116629
- 10d Diez-Gonzalez S, Marion N, Nolan SP. Chem. Rev. 2009; 109: 3612
- 11a Sravanthi TV, Manju SL. Eur. J. Pharm. Sci. 2016; 91: 1
- 11b Yan W, Zhao SS, Ye YH, Zhang YY, Zhang Y, Xu JY, Yin SM, Tan RX. J. Nat. Prod. 2019; 82: 2132
- 11c Palmisanoa G, Penonia A, Sistia M, Tibilettia F, Tollaria S, Nicholas KM. Curr. Org. Chem. 2010; 14: 2409
- 12a Zhang H.-H, Shi F. Acc. Chem. Res. 2022; 55: 2562
- 12b Nasri S, Bayat M, Miankooshki FR, Samet NH. Mol. Diversity 2022; 26: 3411
- 12c Tu M.-S, Chen K.-W, Wu P, Zhang Y.-C, Liu X.-Q, Shi F. Org. Chem. Front. 2021; 8: 2643
- 12d Zhang Y.-C, Jiang F, Shi F. Acc. Chem. Res. 2020; 53: 425
- 12e Mei G.-J, Shi F. Chem. Commun. 2018; 54: 6607
- 12f Yan LJ, Wang YC. ChemistrySelect 2016; 1: 6948
- 13 Bazgir A, Ahadi S, Ghahremanzadeh R, Khavasi HR, Mirzaei P. Ultrason. Sonochem. 2010; 17: 447
- 14 Dandia A, Singh R, Bhaskaran S, Samant SD. Green Chem. 2011; 13: 1852
- 15 Dandia A, Saini D, Bhaskaran S, Saini DK. Med. Chem. Res. 2014; 23: 725
- 16 Dandia A, Parewa V, Jain AK, Rathore KS. Green Chem. 2011; 13: 2135
- 17 Dandia A, Jain AK, Bhati DS. Synth. Commun. 2011; 41: 2905
- 18 Dandia A, Singh R, Joshi J, Maheshwari S, Soni P. RSC Adv. 2013; 3: 18992
- 19 Arya K, Rawat DS, Sasai H. Green Chem. 2012; 14: 1956
- 20 Gholizadeh S, Radmoghadam K. Orient. J. Chem. 2013; 29: 1637
- 21 Hojati SF, Mohamadi S. Org. Prep. Proced. Int. 2020; 52: 304
- 22 Yu CB, Lyu H, Cai Y, Miao XY, Miao ZW. RSC Adv. 2013; 3: 18857
- 23 Liju W, Ablajan K, Jun F. Ultrason. Sonochem. 2015; 22: 113
- 24 Elyasi Z, Ghomi JS, Najafi GR. Ultrason. Sonochem. 2021; 75: 105614
- 25 Li JT, Dai HG, Xu WZ, Li TS. Ultrason. Sonochem. 2006; 13: 24
- 26 Li JT, Sun MX, He GY, Xu XY. Ultrason. Sonochem. 2011; 18: 412
- 27 Joshi RS, Mandhane PG, Diwakar SD, Gill CH. Ultrason. Sonochem. 2010; 17: 298
- 28 Khorshidi A, Tabatabaeian K. J. Serb. Chem. Soc. 2011; 76: 1347
- 29 Li JT, Sun SF, Sun MX. Ultrason. Sonochem. 2011; 18: 42
- 30 Rahimi S, Amrollahi MA, Kheilkordi Z. C. R. Chim. 2015; 18: 558
- 31 Amrollahi MA, Kheilkordi Z. J. Iran. Chem. Soc. 2016; 13: 925
- 32 Shaikh T, Sharma A, Kaur H. ChemistrySelect 2019; 4: 245
- 33 Lu CW, Wang JJ, Liu YH, Shan WJ, Sun Q, Shi L. Res. Chem. Intermed. 2017; 43: 943
- 34 Nikpassand M, Fekri LZ, Nabatzadeh M. Synth. Commun. 2017; 47: 29
- 35 Kasar SB, Thopate SR. Curr. Green Chem. 2018; 5: 177
- 36 Deshmukh SR, Nalkar AS, Thopate SR. Polycyclic Aromat. Compd. 2022; 42: 6501
- 37 Dandia A, Singh R, Bhaskaran S. Ultrason. Sonochem. 2010; 17: 399
- 38 Dandia A, Singh R, Bhaskaran S. Ultrason. Sonochem. 2011; 18: 1113
- 39 Shaikh S, Rasal S, Ramana MM. V. React. Kinet., Mech. Catal. 2021; 133: 405
- 40 Ali A, Ali A, Tahir A, Bakht MA, Ahsan MJ. J. Enzyme Inhib. Med. Chem. 2022; 37: 135