Microwave-Assisted Synthesis of Spiro Heterocycles for Light Emitting Diodes

$40.00

Microwave-Assisted Synthesis of Spiro Heterocycles for Light Emitting Diodes

Priya, Rajni, Riyansha Verma, Sneh Lata, Anjaneyulu Bendi

Spirocyclic molecules are defined as compounds with two rings connected via common atom. As they have structural complexity, distinct conformational characteristics and rigidity, spiro compounds promise to be intriguing skeletal systems in drug discovery. Heterocyclic compounds have incredible significance due to their diverse applications and biological activity. Microwave chemistry involves the application of microwave irradiation to chemical reactions which plays an important role in the synthesis of spiro heterocycles as well as other organic compounds. This chapter aims at highlighting the different approaches for the synthesis of spiro-heterocyclic compounds for pharmacological applications such as anticancer, antimicrobial and anti-inflammatory activity via microwave assisted techniques and in the development of optoelectronic devices.

Keywords
Microwave-Assisted Organic Synthesis, Spiro Heterocycles, Organic Light Emitting Diodes, Spiro-Oxindoles, Multicomponent

Published online 4/5/2026, 21 pages

Citation: Priya, Rajni, Riyansha Verma, Sneh Lata, Anjaneyulu Bendi, Microwave-Assisted Synthesis of Spiro Heterocycles for Light Emitting Diodes, Materials Research Foundations, Vol. 189, pp 134-154, 2026

DOI: https://doi.org/10.21741/9781644904039-5

Part of the book on Microwave-Assisted Synthesis

References
[1] S.N. Afraj, A. Velusamy, M.C. Chen, M. Abd-Ellah, A.L. Abdelhady, Heterocyclic and heteropolycyclic moieties in organic hole transport materials for perovskite solar cells: Design, synthesis, and performance, Coord. Chem. Rev. 532 (2025) 216500. https://doi.org/10.1016/j.ccr.2025.216500
[2] A. Ding, M. Meazza, H. Guo, J.W. Yang, R. Rios, New development in the enantioselective synthesis of spiro compounds, Chem. Soc. Rev. 47 (2018) 5946-5996. https://doi.org/10.1039/C6CS00825A
[3] S. Dhadda, S. Sharma, P. Jakhar, H. Sharma, Contemporary progress in the green synthesis of spiro-thiazolidines and their medicinal significance: a review, RSC Adv. 13 (2023) 3723-3742. https://doi.org/10.1039/D2RA07474E
[4] X.-N. Zhang, X. Dong, Y. Wei, M. Shi, Access to 2′,3′-dihydro-1′H-spiro[indoline-3,4′-pyridin]-2-ones via amino acid derived phosphine-catalyzed asymmetric [4+2] annulation with easily available oxindole-derived α,β-unsaturated imines, Tetrahedron 70 (2014) 2838-2846. https://doi.org/10.1016/j.tet.2014.02.052
[5] P. Saraswat, G. Jeyabalan, M.Z. Hassan, M.U. Rahman, N.K. Nyola, Review of synthesis and various biological activities of spiro heterocyclic compounds comprising oxindole and pyrrolidine moieties, Synth. Commun. 46 (2016) 1643-1664. https://doi.org/10.1080/00397911.2016.1211704
[6] R. Javahershenas, A. Makarem, K.D. Klika, Recent advances in microwave-assisted multicomponent synthesis of spiro heterocycles, RSC Adv. 14 (2024) 5547-5565. https://doi.org/10.1039/D4RA00056K
[7] M. Henary, C. Kananda, L. Rotolo, B. Savino, E.A. Owens, G. Cravotto, Benefits and applications of microwave-assisted synthesis of nitrogen-containing heterocycles in medicinal chemistry, RSC Adv. 10 (2020) 14170-14197. https://doi.org/10.1039/D0RA01378A
[8] S. Gulati, S.E. John, N. Shankaraiah, Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects, Beilstein J. Org. Chem. 17 (2021) 819-865. https://doi.org/10.3762/bjoc.17.71
[9] M. Kamboj, S. Bajpai, G. Pandey, M. Yadav, B.K. Banik, Microwave-assisted synthesis of biologically relevant six-membered N-heterocycles, Curr. Microw. Chem. 10 (2023) 122-134. https://doi.org/10.2174/0122133356268693231114052121
[10] R. Singh, D. Bhardwaj, M.R. Saini, Recent advancement in the synthesis of diverse spiro-indeno[1,2-b]quinoxalines: A review, RSC Adv. 11 (2021) 4760-4804. https://doi.org/10.1039/D0RA09130H
[11] M.A. Borad, M.N. Bhoi, N.P. Prajapati, H.D. Patel, Review of synthesis of Spiro heterocyclic compounds from isatin, Synth. Commun. 44 (2014) 897-922. https://doi.org/10.1080/00397911.2013.843196
[12] N. Lashgari, G. Mohammadi Ziarani, R. Moradi, M. Zandiyeh, 4-Hydroxy-6-methyl-2-pyrone- A versatile synthon in the synthesis of heterocyclic scaffolds via multicomponent reactions, Heterocycles 96 (2018) 381. https://doi.org/10.3987/REV-17-872
[13] M. Mamaghani, R. Hossein Nia, Recent developments in the MCRs synthesis of pyridopyrimidines and Spiro‐pyridopyrimidines: Recent developments in the MCRs synthesis of pyridopyrimidines and Spiro-pyridopyrimidines, J. Heterocycl. Chem. 54 (2017) 1700-1722. https://doi.org/10.1002/jhet.2783
[14] K. Kumar, Microwave‐assisted diversified synthesis of pyrimidines: An overview, J. Heterocycl. Chem. 59 (2022) 205-238. https://doi.org/10.1002/jhet.4376
[15] F. Frecentese, I. Saccone, G. Caliendo, A. Corvino, F. Fiorino, E. Magli, E. Perissutti, B. Severino, V. Santagada, Microwave-assisted organic synthesis of heterocycles in aqueous media: Recent advances in medicinal chemistry, Med. Chem. 12 (2016) 720-732. https://doi.org/10.2174/1573406412666160502153553
[16] B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Small heterocycles in multicomponent reactions, Chem. Rev. 114 (2014) 8323-8359. https://doi.org/10.1021/cr400615v
[17] V. Nigam, S. Singh, S. Kasana, S. Kumar, B. Das Kurmi, G. Das Gupta, P. Patel, Revolutionizing indole synthesis: A microwave‐powered approach, ChemistrySelect 9 (2024). https://doi.org/10.1002/slct.202402171
[18] P. Khanna, L. Khanna, S.J. Thomas, A.M. Asiri, S.S. Panda, Microwave assisted synthesis of Spiro heterocyclic systems: A review, Curr. Org. Chem. 22 (2018) 67-84. https://doi.org/10.2174/1385272821666170818161517
[19] I. Almas, A. Malik, N. Rasool, A. Kanwal, T. Khalid, H. Nawaz, Microwave-assisted protocol towards synthesis of heterocyclic molecules: A comparative analysis with conventional synthetic methodologies (years 2019-2023): A review, Mol. Divers. (2024). https://doi.org/10.1007/s11030-024-10981-y
[20] T.L. Lambat, P.K.P.G. Chopra, S.H. Mahmood, Microwave: A green contrivance for the synthesis of N-heterocyclic compounds, Curr. Org. Chem. 24 (2020) 2527-2554. https://doi.org/10.2174/1385272824999200622114919
[21] Q. Wu, H. Feng, D.-D. Guo, M.-S. Yi, X.-H. Wang, B. Jiang, S.-J. Tu, Microwave-assisted aqueous multicomponent reaction: Facile synthesis of polyfunctionalized indoline-spiro fused pyran derivatives: Synthesis of indoline-spiro fused pyran derivatives, J. Heterocycl. Chem. 50 (2013) 599-602. https://doi.org/10.1002/jhet.1537
[22] D. Luo, Q. Chen, B. Liu, Y. Qiu, Emergence of flexible white organic light-emitting diodes, Polymers (Basel) 11 (2019) 384. https://doi.org/10.3390/polym11020384
[23] X. Yang, X. Xu, G. Zhou, Recent advances of the emitters for high performance deep-blue organic light-emitting diodes, J. Mater. Chem. C Mater. Opt. Electron. Devices 3 (2015) 913-944. https://doi.org/10.1039/C4TC02474E
[24] L. Duan, L. Hou, T.-W. Lee, J. Qiao, D. Zhang, G. Dong, L. Wang, Y. Qiu, Solution processable small molecules for organic light-emitting diodes, J. Mater. Chem. 20 (2010) 6392. https://doi.org/10.1039/b926348a
[25] S. Janietz, H. Krueger, M. Thesen, B. Salert, A. Wedel, Concepts for the material development of phosphorescent organic materials processable from solution and their application in OLEDs, Organic Light Emitting Materials and Devices XVIII (2014) 918303. https://doi.org/10.1117/12.2061005
[26] B. Rávai, A.S. Németh, Z. Kelemen, Erika Bálint, Microwave-assisted multicomponent synthesis of spirooxindole dihydropyridine bisphosphonates, Eur. J. Org. Chem. 28 (2025) e202400873. https://doi.org/10.1002/ejoc.202400873
[27] P. Paul, M. Goswami, D. Chakravarty, S. Joshi, S.R Joshi, R. Nongkhlaw, Microwave-assisted synthesis of spiro heterocyclic scaffolds using graphite oxide as a heterogeneous carbocatalyst and study of their anti-microbial activities, ChemistrySelect 9 (2024) e202402637. https://doi.org/10.1002/slct.202402637
[28] E.V Burgaz, M. Yakut, i. Kunter, Efficient microwave synthesis and anti-cancer evaluation of new substituted 2,4- diazaspiro[5.5] undecane-1,5,9-trione (or 1,3,5,9-tetraone) derivatives, Arkivoc 8 (2024) 202412321. https://doi.org/10.24820/ark.5550190.p012.321
[29] R. Das, D.K Mehta, S. Gupta, S. Mujwar, V. Sharma, A. Goyal, S. Patel, A. Patel, Microwave-assisted synthesis, molecular docking study of spirofused heterocycles as anti-microbial and anthelmintic potential, Letters in Organic Chemistry 20 (2023) 1182-1191. https://doi.org/10.2174/1570178620666230703111452
[30] N.K Sahu, R. Sharma, K.P Suhas, J. Joshi, K. Prakash, R. Sharma, R. Pratap, X. Hu, S. Kaur, M. Jain, C. Coluccini, P. Coghi, S. Chaudhary, Natural-product-inspired microwave-assisted synthesis of novel spirooxindoles as antileishmanial agents: Synthesis, stereochemical assignment, Bioevaluation, SAR, and Molecular Docking Studies, Molecules 28 (2023) 4817. https://doi.org/10.3390/molecules28124817
[31] R. Sharma, L. Yadav, A.A. Nasim, R.K Yadav, R.H. Chen, N. Kumari, F. Ruiqi, A. Sharon, N.K. Sahu, S.K. Ippagunta, P. Coghi, V.K.W. Wong, S. Chaudhary, Chemo-/regio-selective synthesis of novel functionalized spiro[pyrrolidine-2,30-oxindoles] under microwave irradiation and their anticancer activity, Molecules 28 (2023) 6503. https://doi.org/10.3390/molecules28186503
[32] F.H.M. Naglaa, S. A. Rizk, A.E. Galal, A.K. Ali, Expeditious microwavable one‑pot synthesis and biological exploration of spiro[indoline‑3,4′‑pyrazolo[3,4‑b] pyridine derivatives, Journal of the Iranian Chemical Society 19 (2022) 3711-3719. https://doi.org/10.1007/s13738-022-02568-x
[33] S. Shroff, P. P. Mohanta, I. Baitharu, B.P. Bag, A.K. Behera, Microwave-assisted synthesis of novel spiro diarylidenes and their antimicrobial assay, J. Serb. Chem. Soc. 87 (2022) 813-827. https://doi.org/10.2298/JSC210123031S
[34] A. Castro, I.M.G. Andrade, M.C. Coelho, D.P. da Costa, D. das N. Moreira, R.A. Maia, G. da S. Lima, G.F. dos Santos, B.G. Vaz, G.C.G. Militão, P.B.N. da Silva, M.L.A. de A. Vasconcellos, C.G. Lima-Junior, Multicomponent synthesis of spiro 1,3,4‐thiadiazolines with anticancer activity by using deep eutectic solvent under microwave irradiation, J. Heterocyclic Chem. 60 (2023) 392-405. https://doi.org/10.1002/jhet.4591
[35] D.F. Katowah, H.M.E Hassaneen, T.A.Farghaly, Novel Spiro-pyrrolizidine-Oxindole and Spiropyrrolidine-Oxindoles: Green synthesis under classical, ultrasonic, and microwave conditions and molecular docking simulation for antitumor and type 2 diabetes, Arabian Journal of Chemistry 15 (2022) 103930. https://doi.org/10.1016/j.arabjc.2022.103930
[36] S. Bhandari, S. Sana, B. Sridhar, N. Shankaraiah, Microwave‐assisted one‐pot [3+2] cycloaddition of azomethine ylides and 3‐alkenyl oxindoles: A facile approach to pyrrolidine‐fused bis‐spirooxindoles, ChemistrySelect 4 (2019) 1727-1730. https://doi.org/10.1002/slct.201802847
[37] S. Nayak, P. Panda, S. Mohapatra, B. Raiguru, N. Baral, Microwave‐assisted one‐pot, three‐component regiospecific and sterospecific synthesis of Spiro indanone pyrrolidine/piperidine fused nitrochromene derivatives through 1,3‐dipolar cycloaddition reactions, J. Heterocyclic Chem. 56 (2019) 1757-1770. https://doi.org/10.1002/jhet.3534
[38] A. Mondal, B. Naskar, S. Goswami, C. Prodhan, K. Chaudhuri, C. Mukhopadhyay, A quick accelerating microwave-assisted sustainable technique: permutated spiro-casing for imaging experiment, Mol. Divers. 24 (2020) 93-106. https://doi.org/10.1007/s11030-019-09934-7
[39] P.N. Shinde, M.A. Raskar, Synthesis and biological evaluation of Spiro (indole-thiazolidine) derivatives as antimicrobial agents, Int. J. Curr. Pharm. Res. 11 (2019) 71-74. https://doi.org/10.22159/ijcpr.2019v11i6.36346
[40] S. Khojasteh-Khosro, H. Shahbazi-Alavi, Preparation of spirooxindoles catalyzed by nano-Co3S4 under microwave irradiations, J. Chem. Res. 43 (2019) 107-111. https://doi.org/10.1177/1747519819841791
[41] H. Gazzeh, S. Boudriga, M. Askri, A. Khatyr, M. Knorr, C. Strohmann, C. Golz, Y. Rousselin, M.M. Kubicki, Stoichiometry-controlled cycloaddition of nitrilimines with unsymmetrical exocyclic dienones: Microwave-assisted synthesis of novel mono- and dispiropyrazoline derivatives, RSC Adv. 6 (2016) 49868-49875. https://doi.org/10.1039/C6RA09703K
[42] Y.X. Zhang, L. Ding, X.Y. Liu, Z.Q. Jiang, H. Chen, S.J. Ji, L.S. Liao, Spiro-fused N-phenylcarbazole-based host materials for blue phosphorescent organic light-emitting diodes, Organic Electronics. 20 (2015) 112-118. https://doi.org/10.1016/j.orgel.2015.02.014
[43] Y. Qian, G. Xie, S. Chen, Z. Liu, Y. Ni, X. Zhou, L. Xie, J. Liang, Y. Zhao, M. Yi, Y. Zhao, W. Wei, W. Huang, A new spiro[fluorene-9,90-xanthene]-based host material possessing no conventional hole- and electron-transporting units for efficient and low voltage blue PHOLED via simple two-step synthesis, Organic Electronics. 13 (2012) 2741-2746. https://doi.org/10.1016/j.orgel.2012.07.047
[44] X.Y. Liu, X. Tang, D. Zhao, B. Song, L. Ding, J. Fan, L.-S. Liao, A series of spirofluorene-based host materials for efficient phosphorescent organic light-emitting diodes, Organic Electronics. 61 (2018) 70-77. https://doi.org/10.1016/j.orgel.2018.06.046
[45] L. He, B.-L. Qu, M. Xiao, J.-Q. Yu, J. Yu, Y. Cheng, Z. Zhang, W.-J. Xiao, L.-Q. Lu, Synthesis of chiral spiro-indenes via Pd-catalyzed asymmetric (4 + 2) dipolar cyclization. Chem. Synth. 4 (2024). https://doi.org/10.20517/cs.2024.39
[46] S.O. Jeon, K.S. Yook, J.Y. Lee, Pyridine substituted spirofluorene derivative as an electron transport material for high efficiency in blue organic light-emitting diodes, Thin Solid Films 519 (2010) 890-893. https://doi.org/10.1016/j.tsf.2010.08.108