Métodos sostenibles para la síntesis de cromenos: avances recientes

Autores/as

DOI:

https://doi.org/10.24215/23143991e006

Palabras clave:

síntesis, cromenos, heterociclo, reacción multicomponente, catalizador heterogéneo

Resumen

La búsqueda de procesos químicos ambientalmente amigables y alineados con los principios de la Química Verde ha cobrado un interés creciente en los últimos años. En este contexto, la síntesis multicomponente ha emergido como una estrategia clave en Química Orgánica, permitiendo la obtención de heterociclos con potencial actividad biológica, como los cromenos. Estos compuestos poseen un alto valor en la industria farmacéutica y exhiben un amplio espectro de bioactividades. En consecuencia, se han desarrollado diversas metodologías para su síntesis, junto con una amplia gama de materiales catalíticos. Entre los enfoques más estudiados destacan la irradiación por microondas y ultrasonido, debido a su eficiencia y sostenibilidad. En esta revisión, se presentan y analizan los métodos de síntesis que cumplen con los principios de la Química Verde, promoviendo procesos altamente sostenibles y de menor impacto ambiental.

Referencias

Abd El-Hameed, R. H., Mohamed, M. S., Awad, S. M., Hassan, B. B., Khodair, M. A. E. F. y Mansour, Y. E. (2023). Novel benzo chromene derivatives: Design, synthesis, molecular docking, cell cycle arrest, and apoptosis induction in human acute myeloid leukemia HL-60 cells. Journal of Enzyme Inhibition and Medicinal Chemistry, 38(1), 405-422. https://doi.org/10.1080/14756366.2022.2151592

Agrawal, N., Goswami, R. y Pathak, S. (2024). Synthetic methods for various chromeno-fused heterocycles and their potential as antimicrobial agents. Medicinal Chemistry, 20(2), 115-129. https://doi.org/10.2174/0115734064274748231005074100

Akbari, A. (2017). Photochemical synthesis of benzo [f] chromene. Photochemical & Photobiological Sciences, 16(12), 1778-1783. https://doi.org/10.1039/C7PP00302A

Anaikutti, P., Adhikari, P., Baskaran, S., Selvaraj, M., Afzal, M. y Makam, P. (2024). Indolyl‐4H‐Chromene Derivatives as Antibacterial Agents: Synthesis, in Vitro and in Silico Studies. Chemistry & Biodiversity, 21(1), e202301392. https://doi.org/10.1002/cbdv.202301392

Arzehgar, Z., Azizkhani, V., Sajjadifar, S. y Fekri, M. H. (2019). Synthesis of 2-amino-4h-chromene derivatives under solvent-free condition using MOF-5. Chemical Methodologies, 3(2), 251-260. https://doi.org/10.22034/chemm.2018.149048.1089

Azizkhani, V., Amirloo, M. R., Mohammadi, B. y Moradi, A. R. (2017). One-pot catalytic multicomponent synthesis of chromene derivatives by 1-allyl-3-methyl-imidazolium halides. Revue Roumaine de Chimie, 62(11), 831-837.

Baghernejad, B. y Koosha, S. (2020). One-pot Synthesis of 2-amino-4H-chromene derivatives as potential antimicrobial agents using DABCO-CuCl complex as an effective catalyst. Journal of Applied Chemical Research, 14(3), 19-25. https://dorl.net/dor/20.1001.1.20083815.2020.14.3.2.8

Chadha, M., Garg, A., Bhalla, A. y Berry, S. (2024). Green methods mediated synthesis of chromene derivatives using magnetic nanoparticles as heterogeneous and reusable nanocatalyst: A review. Tetrahedron, 150(133741). https://doi.org/10.1016/j.tet.2023.133741

Chatterjee, R., Bhukta, S. y Dandela, R. (2022) Ionic liquid-assisted synthesis of 2-amino-3-cyano-4H chromenes: A sustainable overview. Journal of Heterocyclic Chemistry, 59, 633–654. https://doi.org/10.1002/jhet.4417

Cherif, M., Debbabi, M., Chortani, S., Romdhane, A. y Jannet, H. B. (2018). Design and synthesis of new naphtho [2, 1-b] pyrano [2, 3-d] pyrimidinones under classical and microwave conditions. Turkish Journal of Chemistry, 42(6), 1623-1639. https://doi.org/10.3906/kim-1803-84

Esfandiary, N., Nakisa, A., Azizi, K., Azarnia, J., Radfar, I. y Heydari, A. (2017). Glucose‐coated superparamagnetic nanoparticle‐catalysed pyrazole synthesis in water. Applied Organometallic Chemistry, 31(7), e3641. https://doi.org/10.1002/aoc.3641

Gadhave, A. y Uphade, B. (2020). One-pot synthesis of 2-amino-4h-chromenes using chicken eggshell waste as green catalyst under solvent-free conditions. Indian Journal of Heterocyclic Chemistry, 30(3), 387-394.

Ghabdian, K., Motavalizadehkakhky, A., Zhiani, R., Allahresani, A. y Ghabdian, M. (2024). Cu (II) salen complex grafted onto KCC-1 as a convenient multifunctional heterogeneous catalyst for the preparation of 4 H-benzochromenes. Research on Chemical Intermediates, 50(7), 3179-3196. https://doi.org/10.1007/s11164-024-05311-8

Ghorbani, F., Pourmousavi, S. A. y Kiyani, H. (2021). Synthesis and characterization of pine-cone derived carbon-based solid acid: A green and recoverable catalyst for the synthesis of pyrano_ pyrazole, amino-benzochromene, amidoalkyl naphthol and thiazolidinedione derivatives. Letters in Organic Chemistry, 18(1), 66-81. https://doi.org/10.2174/1570178617666200210105635

Kafi‐Ahmadi, L., Poursattar Marjani, A. y Nozad, E. (2021). Ultrasonic‐assisted preparation of Co3O4 and Eu‐doped Co3O4 nanocatalysts and their application for solvent‐free synthesis of 2‐amino‐4H‐benzochromenes under microwave irradiation. Applied Organometallic Chemistry, 35(8), e6271. https://doi.org/10.1002/aoc.6271

Kantharaju, K. y Khatavi, S. Y. (2018). A green method synthesis and antimicrobial activity of 2-amino-4H-chromene derivatives. Asian Journal of Chemistry, 30(7), 1496-1502. https://doi.org/10.14233/ajchem.2018.21191

Katiyar, M. K., Dhakad, G. K., Arora, S., Bhagat, S., Arora, T. y Kumar, R. (2022). Synthetic strategies and pharmacological activities of chromene and its derivatives: An overview. Journal of Molecular Structure, 1263(133012). https://doi.org/10.1016/j.molstruc.2022.133012

Khaledi-koureh, B., Kafi-Ahmadi, L., Khademinia, S. y Marjani, A. P. (2023). Synthesis, physical and electrochemical properties of Bi-VO mixed metal oxide nanocomposites for catalytic fabrication of 2-amino-4H-benzochromenes under heat, ultrasonic, and microwave illuminations. Journal of Molecular Structure, 1277(134832). https://doi.org/10.1016/j.molstruc.2022.134832

Khazaee, A., Jahanshahi, R., Sobhani, S., Skibsted, J. y Sansano, J. M. (2020). Immobilized piperazine on the surface of graphene oxide as a heterogeneous bifunctional acid–base catalyst for the multicomponent synthesis of 2-amino-3-cyano-4 H-chromenes. Green Chemistry, 22(14), 4604-4616. https://doi.org/10.1039/D0GC01274B

Kheirkhah, L., Mamaghani, M., Mahmoodi, N. O., Yahyazadeh, A. y Ziabari, S. S. M. (2017). Studies on the Synthesis of Substituted 2-amino-4 H-benzo [h] chromene and 3-amino-1 H-benzo [f] chromene Derivatives Using Base Supported Ionic Liquid Like-phase (SILLP) as an Efficient Green Catalyst. Journal of Chemical Research, 41(1), 21-24. https://doi.org/10.3184/174751917X14815427219202

Kiasat, A. R., Hamid, S. y Saghanezhad, S. J. (2019). Bipyridinium chloride supported rice husk silica: An efficient nanocomposite for the one-pot preparation of spirooxindole pyran and 2-amino-4H chromene derivatives. Revue Roumaine de Chimie, 64(11), 927-934. https://doi.org/10.33224/rrch/2019.64.11.01

Li, Y., Ma, T., Yang, Y., Zhong, X., Zhu, G., Wang, J. y Fan, L. (2024). Synthesis of Novel Chromene Derivatives Bearing Hydrazide/Thiazol/Oxazol/Oxime Moieties as Potential Antifungal Agents. Journal of Agricultural and Food Chemistry, 72(48), 26983-26995. https://doi.org/10.1021/acs.jafc.4c07704

Mamaghani, M., Nia, R. H., Tavakoli, F. y Jahanshahi, P. (2018). Recent advances in the MCRs synthesis of chromenes: A review. Current Organic Chemistry, 22(17), 1704-1769. https://doi.org/10.2174/1385272822666180530104302

Mobinikhaledi, A., Moghanian, H. y Ghanbari, M. (2018). Synthesis and characterization of sodium polyaspartate‐functionalized silica‐coated magnetite nanoparticles: A heterogeneous, reusable and magnetically separable catalyst for the solvent‐free synthesis of 2‐amino‐4H‐chromene derivatives. Applied Organometallic Chemistry, 32(3), e4108. https://doi.org/10.1002/aoc.4108

Mohammadi, R., Esmati, S., Gholamhosseini-Nazari, M. y Teimuri-Mofrad, R. (2019). Synthesis and characterization of a novel Fe3O4@ SiO2–BenzIm-Fc [Cl]/BiOCl nano-composite and its efficient catalytic activity in the ultrasound-assisted synthesis of diverse chromene analogs. New Journal of Chemistry, 43(1), 135-145. https://doi.org/10.1039/C8NJ04938F

Nabinia, N., Shirini, F., Tajik, H., Mashhadinezhad, M. y Langarudi, M. S. N. (2018). An affordable DABCO-based ionic liquid efficiency in the synthesis of 3-amino-1-aryl-1H-benzo[f] chromene-2-carbonitrile, 1-(benzothiazolylamino)phenylmethyl-2-naphthol, and 1-(benzoimidazolylamino)phenylmethyl-2-naphthol derivatives. Journal of the Iranian Chemical Society, 15, 2147-2157. https://doi.org/10.1007/s13738-018-1408-x

Neela, A., Clarina, T. y Rama, V. (2019). Nickel oxide-catalyzed synthesis of 4-amino-2H-chromenes: Its application in antimicrobial studies and towards protein docking. Asian Journal of Chemistry, 31(5), 1049-1056.

Nope Vargas, E. R. (2021). Sólidos básicos como catalizadores en la síntesis ecoeficiente de heterociclos potencialmente activos [Tesis de doctorado, Universidad Nacional de La Plata]. http://sedici.unlp.edu.ar/handle/10915/114455

Palermo, V., Sosa, A. A., Rivera, T. S., Pizzio, L. R. y Romanelli, G. P. (2019). Unexpected Result in the Catalytic Solvent-free Multicomponent Synthesis of 2-Amino-3-cyano-4 H-chromene. Organic Preparations and Procedures International, 51(5), 443-455. https://doi.org/10.1080/00304948.2018.1549903

Papi, S., Jamehbozorgi, S., Yazdanipour, A. y Ramezani, M. (2023). Fe3O4@ SiO2@ propyl‐AMP/Co: A new catalyst for the synthesis of benzopyrans. Journal of Organometallic Chemistry, 995, 122729. https://doi.org/10.1016/j.jorganchem.2023.122729

Patil, U. P., Patil, R. C. y Patil, S. S. (2019). An Eco‐friendly Catalytic System for One‐pot Multicomponent Synthesis of Diverse and Densely Functionalized Pyranopyrazole and Benzochromene Derivatives. Journal of Heterocyclic Chemistry, 56(7), 1898-1913. https://doi.org/10.1002/jhet.3564

Patil, S. P., Shinde, S. K. y Patil, S. S. (2022). Coconut endocarp shell ash (CESA): A non-conventional catalyst for green synthesis of 2-amino-4 H-benzochromenes. Research on Chemical Intermediates, 48(12), 5003-5027. https://doi.org/10.1007/s11164-022-04847-x

Pertino, M. W., F de la Torre, A., Schmeda-Hirschmann, G., Vega Gómez, C., Rolón, M., Coronel, C., Rojas de Arias, A., Molina-Torres, C. A.,Vera-Cabrera, L. y Viveros-Valdez, E. (2024). Exploring benzo [h] chromene derivatives as agents against protozoal and mycobacterial infections. Pharmaceuticals, 17(10), 1375. https://doi.org/10.3390/ph17101375.

Pourhasan, B. y Mohammadi‐Nejad, A. (2019). Piperazine‐functionalized nickel ferrite nanoparticles as efficient and reusable catalysts for the solvent‐free synthesis of 2‐amino‐4H‐chromenes. Journal of the Chinese Chemical Society, 66(10), 1356-1362. https://doi.org/10.1002/jccs.201800291

Raj, V. y Lee, J. (2020). 2H/4H-Chromenes-A versatile biologically attractive Scaffold. Frontiers in Chemistry, 8, 623. https://doi.org/10.3389/fchem.2020.00623

Sadjadi, S., Heravi, M. M., Zadsirjan, V. y Ebrahimizadeh, M. (2017). SBA-15@ methenamine-HPA: a novel, simple, and efficient catalyst for one-pot three-component synthesis of 2-amino-4 H-chromene derivatives in aqueous medium. Research on Chemical Intermediates, 43, 5467-5483. https://doi.org/10.1007/s11164-017-2940-5

Sarmah, B. y Srivastava, R. (2017) Highly efficient and recyclable basic ionic liquids supported on SBA-15 for the synthesis of substituted styrenes, carbinolamides, and naphthopyrans. Journal of Molecular Catalysis A: Chemical, 427, 62–72. https://doi.org/10.1016/j.molcata.2016.11.030

Shaban, S. S., Haneen, D. S., Abou-El-Regal, M. M. y El-Metwally, S. A. (2024). Design, synthesis and antibacterial assessment of novel 4 H-chromene analogues. Synthetic Communications, 54(7), 600-611. https://doi.org/10.1080/00397911.2024.2324009

Shamili, S., Chandrakala, G., Farheen, S. I. y Kavitha, S. (2023). Synthesis and Antimicrobial Activity of Novel (1-Aryl-1 H-1, 2, 3-triazol-4-yl) methyl 3-Acetamido-1-phenyl-1 H-benzo [f] chromene-2-carboxylates. Russian Journal of Organic Chemistry, 59(6), 1033-1040. https://doi.org/10.1134/S1070428023060106

Taheri, N., Fallah-Mehrjardi, M. y Sayyahi, S. (2018). Polystyrene-supported 1-methylimidazolium tetrachloro ferrate: Synthesis, characterization, and application as an efficient and reusable heterogeneous catalyst for one-pot synthesis of 4h-chromene derivatives in aqueous media. Bulletin of the Chemical Society of Ethiopia, 32(3), 531-540. https://doi.org/10.4314/bcse.v32i3.12

Taib, L. A., Keshavarz, M. y Parhami, A. (2021). Solvent‐free synthesis of compounds containing chromene core catalyzed by novel Brønsted acidic ionic liquids‐ClO4. Journal of the Chinese Chemical Society, 68(6), 1128-1137. https://doi.org/10.1002/jccs.202000449

Teimuri‐Mofrad, R., Gholamhosseini‐Nazari, M., Payami, E. y Esmati, S. (2018). Ferrocene‐tagged ionic liquid stabilized on silica‐coated magnetic nanoparticles: Efficient catalyst for the synthesis of 2‐amino‐3‐cyano‐4H‐pyran derivatives under solvent‐free conditions. Applied Organometallic Chemistry, 32(1), e3955. https://doi.org/10.1002/aoc.3955

Thabet, H. K., Ragab, A., Imran, M., Helal, M. H., Alaqel, S. I., Alshehri, A., Mohd A. A., Alshammari, S. S., Ammar. Y. A. y Abusaif, M. S. (2024). Innovation of 6-sulfonamide-2 H-chromene derivatives as antidiabetic agents targeting α-amylase, α-glycosidase, and PPAR-γ inhibitors with in silico molecular docking simulation. RSC advances, 14(22), 15691-15705. https://doi.org/10.1039/d4ra02143f

Vanga, M. K., Bhukya, R., Thumma, V., Tamalapakula, V., Boddu, L. S. y Manga, V. (2024). Antioxidant and Antimicrobial Activities of 4H‐Chromene Based Indole‐Pyrimidine Hybrids: Synthesis and Molecular Docking Studies. Chemistry & Biodiversity, 21(12), e202401583. https://doi.org/10.1002/cbdv.202401583

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2025-07-18

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Pérez, M. E., & Nope Vargas, E. R. (2025). Métodos sostenibles para la síntesis de cromenos: avances recientes. Investigación Joven, 12, e006. https://doi.org/10.24215/23143991e006