Facile one-pot green synthesis of 2-amino-4H-benzo[g]chromenes in aqueous ethanol under ultrasound irradiation

References

• Maleki, B.; Babaee, S.; Tayebee, R. Zn (L-Proline)2 as a Powerful and Reusable Organometallic Catalyst for the Very Fast Synthesis of 2-Amino-4H-Benzo[g]Chromene Derivatives under Solvent-Free Conditions. Appl. Organometal. Chem. 2015, 29, 408–411. DOI: 10.1002/aoc.3306.
   Web of Science ®Google Scholar
• Yang, F.; Wang, H.; Jiang, L.; Yue, H.; Zhang, H.; Wang, Z.; Wang, L. A Green and One-Pot Synthesis of Benzo[g]Chromene Derivatives through a Multi-Component Reaction Catalyzed by Lipase. RSC Adv. 2015, 5, 5213–5216. DOI: 10.1039/C4RA13272F.
   Web of Science ®Google Scholar
• Wang, X. H.; Zhang, X. H.; Tu, S. J.; Shi, F.; Zou, X.; Yan, S.; Han, Z.-G.; Hao, W. J.; Cao, X. D.; Wu, S. S. A Facile Route to the Synthesis of 1,4-Pyranonaphthoquinone Derivatives under Microwave Irradiation without Catalyst. J. Heterocyclic Chem. 2009, 46, 832–836. DOI: 10.1002/jhet.153.
   Web of Science ®Google Scholar
• Khurana, J. M.; Nand, B.; Saluja, P. DBU: A Highly Efficient Catalyst for One-Pot Synthesis of Substituted 3,4-Dihydropyrano[3,2-c]Chromenes, Dihydropyrano[4,3-b]Pyranes, 2-Amino-4H-Benzo[h]Chromenes and 2-Amino-4H Benzo[g]Chromenes in Aqueous Medium. Tetrahedron 2010, 66, 5637–5641. DOI: 10.1016/j.tet.2010.05.082.
   Web of Science ®Google Scholar
• Silva, J. P. E.; de Araujo, N. M.; da Silva Emery, F. Claisen Rearrangement of Hydroxynaphthoquinones: Selectivity toward Naphthofuran or α-Xiloidone Using Copper Salts and Iodine. J. Heterocyclic Chem. 2015, 52, 518–521. DOI: 10.1002/jhet.2087.
   Web of Science ®Google Scholar
• Shaabani, A.; Ghadari, R.; Ghasemi, S.; Pedarpour, M.; Rezayan, A. H.; Sarvary, A.; Ng, S. W. Novel One-Pot Three- and Pseudo-Five-Component Reactions: Synthesis of Functionalized Benzo[g]- and Dihydropyrano[2,3-g]Chromene Derivatives. J. Comb. Chem. 2009, 11, 956–959. DOI: 10.1021/cc900101w.
   PubMedGoogle Scholar
• Safaei-Ghomi, J.; Eshteghal, F.; Shahbazi-Alavi, H. A Facile One-Pot Ultrasound Assisted for an Efficient Synthesis of Benzo[g]Chromenes Using Fe3O4/Polyethylene Glycol (PEG) Core/Shell Nanoparticles. Ultrason. Sonochem. 2016, 33, 99–105. DOI: 10.1016/j.ultsonch.2016.04.025.
   PubMed Web of Science ®Google Scholar
• Khurana, J. M.; Magoo, D.; Chaudhary, A. Efficient and Green Approaches for the Synthesis of 4H-Benzo[g]Chromenes in Water, under Neat Conditions, and Using Task-Specific Ionic Liquid. Synth. Commun. 2012, 42, 3211–3219. DOI: 10.1080/00397911.2011.580069.
   Web of Science ®Google Scholar
• Maleki, B. One-Pot Synthesis of Some 2-Amino-4H-Benzo[g]Chromenes. Org. Prep. Proced. Int. 2016, 48, 81–87. DOI: 10.1080/00304948.2016.1127104.
   Web of Science ®Google Scholar
• Banerjee, B. Recent Developments on Ultrasound Assisted Catalyst-Free Organic Synthesis. Ultrason. Sonochem. 2017, 35, 1–14. DOI: 10.1016/j.ultsonch.2016.09.023.
   PubMed Web of Science ®Google Scholar
• Patil, R.; Bhoir, P.; Deshpande, P.; Wattamwar, T.; Shirude, M.; Chaskar, P. Relevance of Sonochemistry or Ultrasound (US) as a Proficient Means for the Synthesis of Fused Heterocycles. Ultrason. Sonochem. 2013, 20, 1327–1336. DOI: 10.1016/j.ultsonch.2013.04.002.
   PubMed Web of Science ®Google Scholar
• Cintas, P.; Luche, J. L. Green Chemistry. The Sonochemical Approach. Green Chem. 1999, 1, 115–125. DOI: 10.1039/a900593e.
   Web of Science ®Google Scholar
• Lupacchini, M.; Mascitti, A.; Giachi, G.; Tonucci, L.; d’Alessandro, N.; Martinez, J.; Colacino, E. Sonochemistry in Non-Conventional, Green Solvents or Solvent-Free Reactions. Tetrahedron 2017, 73, 609–653. DOI: 10.1016/j.tet.2016.12.014.
   Web of Science ®Google Scholar
• Ashokkumar, M. The Characterization of Acoustic Cavitation Bubbles – An Overview. Ultrason. Sonochem. 2011, 18, 864–872. DOI: 10.1016/j.ultsonch.2010.11.016.
   PubMed Web of Science ®Google Scholar
• Naeimi, H.; Didar, A. Efficient Sonochemical Green Reaction of Aldehyde, Thiobarbituric Acid and Ammonium Acetate Using Magnetically Recyclable Nanocatalyst in Water. Ultrason. Sonochem. 2017, 34, 889–895. DOI: 10.1016/j.ultsonch.2016.07.021.
   PubMed Web of Science ®Google Scholar
• Leong, T.; Ashokkumar, M.; Kentish, S. The Fundamentals of Power ultrasound-A Review. Acoust. Aust. 2011, 39, 54–63.
   Web of Science ®Google Scholar
• Mohammadi, R.; Esmati, S.; Gholamhosseini-Nazari, M.; Teimuri-Mofrad, R. Synthesis and Characterization of a Novel Fe3O4@SiO2–BenzIm-Fe[Cl]/BiOCl Nano-Composite and Its Efficient Catalytic Activity in the Ultrasound-Assisted Synthesis of Diverse Chromene Analogs. New J. Chem. 2019, 43, 135–145. DOI: 10.1039/C8NJ04938F.
   Web of Science ®Google Scholar
• Sajjadifar, S.; Amini, I.; Amoozadeh, T. Silica Boron Sulfonic Acid as a New and Efficient Catalyst for the Green Synthesis of Quinoxaline Derivatives at Room Temperature. Chem. Method. 2017, 1, 1–11. DOI: 10.22631/chemm.2017.88920.1000.
   Google Scholar
• Hosseinzadeh, Z.; Ramazani, A.; Ahankar, H.; Ślepokura, K.; Lis, T. Sulfonic Acid-Functionalized Silica-Coated Magnetic Nanoparticles as a Reusable Catalyst for the Preparation of Pyrrolidinone Derivatives under Eco-Friendly Conditions. Silicon 2019, 11, 2933–2943. DOI: 10.1007/s12633-019-0087-2.
   Web of Science ®Google Scholar
• Ramazani, A.; Ahankar, H.; Nafeh, Z. T.; Joo, S. W. Modern Catalysts in A3-Coupling Reactions. COC 2020, 23, 2783–2801. DOI: 10.2174/1385272823666191113160643.
   Google Scholar
• Bommeraa, R. K.; Merugu, R.; Eppakayala, L. A Facile Synthesis and Docking Studies of N-(3-(4-Chlorophenoxy)Benzyl)-2-Methyl-7H-Pyrrolo[2,3-d]Pyrimidin-4-Amine. Chem. Methodol. 2019, 3, 354–361.
   Google Scholar
• Ramazani, A.; Sadighian, H.; Gouranlou, F.; Joo, S. W. Syntheses and Biological Activities of Triazole-Based Sulfonamides. COC 2020, 23, 2319–2349. DOI: 10.2174/1385272823666191021115023.
   Google Scholar
• Hosseinzadeh, Z.; Ramazani, A.; Razzaghi-Asl, N. Anti-Cancer Nitrogen-Containing Heterocyclic Compounds. COC 2018, 22, 2256–2279. DOI: 10.2174/1385272822666181008142138.
   Google Scholar
• Sajjadifar, S.; Azizkhania, V.; Pal, K.; Jabbar, H.; Pouralimardan, O.; Divsar, F.; Mohammadi-Aghdam, S.; Amini, I.; Hamidi, H. Characterization of Catalyst: Comparison of Bronsted and Lewis Acidic Power in Boron Sulfonic Acid as a Heterogeneous Catalyst in Green Synthesis of Quinoxaline Derivatives. Chem. Method. 2017, 1, 1–236. DOI: 10.22631/chemm.2017.88920.1000.
   Google Scholar
• Nezhad, E. R.; Tahmasebi, R. Ionic Liquid Supported on Magnetic Nanoparticles as an Efficient and Reusable Green Catalyst for Synthesis of Benzimidazole Derivatives under Solvent and Solvent-Free Conditions. Asian J. Green Chem. 2019, 1, 34–42.
   Google Scholar
• Hassani, H.; Zakerinasab, B.; Nozarie, A. Sulfonic Acid Supported on Fe2O3/VO2 Nanocatalyst: A Highly Efficient and Reusable Nanocatalyst for Synthesis of Spirooxindole Derivatives. Asain. J. Green Chem. 2018, 3, 59–69. DOI: 10.22631/ajgc.2017.101572.1032.
   Google Scholar
• Ramazani, A.; Khoobi, M.; Torkaman, A.; Nasrabadi, Z. F.; Forootanfar, H.; Shakibaie, M.; Jafari, M.; Ameri, A.; Emami, S.; Faramarzi, M. A.; et al. One-Pot, Four-Component Synthesis of Novel Cytotoxic Agents 1-(5-Aryl-1,3,4-Oxadiazol-2-yl)-1-(1H-Pyrrol-2-yl)Methanamines. Eur. J. Med. Chem. 2014, 78, 151–156. DOI: 10.1016/j.ejmech.2014.03.049.
   PubMed Web of Science ®Google Scholar
• Kazemi, M.; Sajjadifar, S.; Aydi, A.; Heydari, M. M. Biological and Pharmaceutical Organosulfur Molecules. J. Med. Chem. Sci. 2018, 1, 1–4.
   Google Scholar
• Dayyani, N.; Khoee, S.; Ramazani, A. Design and Synthesis of pH-Sensitive Polyamino-Ester Magneto-Dendrimers: Surface Functional Groups Effect on Viability of Human Prostate Carcinoma Cell Lines DU145. Eur. J. Med. Chem. 2015, 98, 190–202. DOI: 10.1016/j.ejmech.2015.05.028.
   PubMed Web of Science ®Google Scholar
• Hasani, H.; Irizeh, M. One-Pot Synthesis of Spirooxindole Derivatives Catalyzed by ZnFe2O4 as a Magnetic Nanoparticles. Asain. J. Green Chem. 2017, 0, 0–95. DOI: 10.22631/ajgc.2017.101002.1025.
   Google Scholar
• Yavari, I.; Ramazani, A. An Efficient One-Pot Synthesis of Dialkyl 3H-Naphtho[2,1,b]Pyran-2,3-Dicarboxylates Mediated by Vinyl Triphenylphosphonium Salt. Synth. Commun. 1997, 27, 1385–1390. DOI: 10.1080/00397919708006068.
   Web of Science ®Google Scholar
• Yavari, I.; Ramazani, A.; Yahya-Zadeh, A. Synthesis of Densely Functionalized N-Hydroxypyrroles Mediated by Vinyltriphenylphosphonium Salt. Synth. Commun. 1996, 26, 4495–4499. DOI: 10.1080/00397919608003851.
   Web of Science ®Google Scholar
• Ahankar, H.; Ramazani, A.; Ślepokura, K.; Lis, T.; Joo, S. W. Synthesis of Pyrrolidinone Derivatives from Aniline, an Aldehyde and Diethyl Acetylenedicarboxylate in an Ethanolic Citric Acid Solution under Ultrasound Irradiation. Green Chem. 2016, 18, 3582–3593. DOI: 10.1039/C6GC00157B.
   Web of Science ®Google Scholar
• Kaur, R.; Kumar, K. A Journey towards FeCl3 Catalysed Synthesis of Multisubstituted Pyrrole. J. Med. Chem. Sci. 2019, 2, 110–117.
   Google Scholar
• Fardood, S. T.; Ramazani, A.; Moradi, S. Green Synthesis of Ni–Cu–Mg Ferrite Nanoparticles Using Tragacanth Gum and Their Use as an Efficient Catalyst for the Synthesis of Polyhydroquinoline Derivatives. J. Sol-Gel Sci. Technol. 2017, 82, 432–439. DOI: 10.1007/s10971-017-4310-6.
   Web of Science ®Google Scholar
• Khoobi, M.; Foroumadi, A.; Emami, S.; Safavi, M.; Dehghan, G.; Alizadeh, B. H.; Ramazani, A.; Ardestani, S. K.; Shafiee, A. Coumarin-Based Bioactive Compounds: Facile Synthesis and Biological Evaluation of Coumarin-Fused 1,4-Thiazepines. Chem. Biol. Drug. Des. 2011, 78, 580–586. DOI: 10.1111/j.1747-0285.2011.01175.x.
   PubMed Web of Science ®Google Scholar
• Khoobi, M.; Emami, S.; Dehghan, G.; Foroumadi, A.; Ramazani, A.; Shafiee, A. Synthesis and Free Radical Scavenging Activity of Coumarin Derivatives Containing a 2-Methylbenzothiazoline Motif. Arch. Pharm. Pharm. Med. Chem. 2011, 344, 588–594. DOI: 10.1002/ardp.201000271.
   PubMed Web of Science ®Google Scholar
• Ramazani, A.; Reza-Kazemizadeh, A. Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Applications. COC 201, 15, 3986–4020. DOI: 10.2174/138527211798072412.
   Google Scholar
• Moghadasi, Z. One-Pot Synthesis of 2-Amino-4H-Chromenes Using L-Prolineas a Reusable Catalyst. J. Med. Chem. Sci. 2019, 2, 35–37.
   Google Scholar
• Ramazani, A.; Mahyari, A. T.; Rouhani, M.; Rezaei, A. A Novel Three-Component Reaction of a Secondary Amine and a 2-Hydroxybenzaldehyde Derivative with an Isocyanide in the Presence of Silica Gel: An Efficient One-Pot Synthesis of Benzo[b]Furan Derivatives. Tetrahedron Lett. 2009, 50, 5625–5627. DOI: 10.1016/j.tetlet.2009.07.115.
   Web of Science ®Google Scholar
• Aghahosseini, H.; Ramazani, A.; Jalayer, N. S.; Ranjdoost, Z.; Souldozi, A.; Ślepokura, K.; Lis, T. Vinylphosphonium Salt-Mediated Reactions: A One-Pot Condensation Approach for the Highly Cis-Selective Synthesis of N-Benzoylaziridines and the Green Synthesis of 1,4,2-Dioxazoles as Two Important Classes of Heterocyclic Compounds. Org. Lett. 2019, 21, 22–26. DOI: 10.1021/acs.orglett.8b03388.
   PubMed Web of Science ®Google Scholar
• Aghahosseini, H.; Ramazani, A.; Ślepokura, K.; Lis, T. The First Protection-Free Synthesis of Magnetic Bifunctional L-Proline as a Highly Active and Versatile Artificial Enzyme: Synthesis of Imidazole Derivatives. J. Colloid. Interf. Sci. 2018, 511, 222–232. DOI: 10.1016/j.jcis.2017.10.020.
   PubMed Web of Science ®Google Scholar
• Gonzalez-Balderas, R. M.; Velasquez-Orta, S. B.; Valdez-Vazquez, I.; Orta-Ledesma, M. T. Intensified Recovery of Lipids, Proteins, and Carbohydrates from Wastewater-Grown Microalgae Desmodesmus sp. by Using Ultrasound or Ozone. Ultrason. Sonochem. 2020, 62, 104862.
   PubMed Web of Science ®Google Scholar
• Aghahosseini, H.; Ramazani, A. Magnetite L-Proline as a Reusable Nano-Biocatalyst for Efficient Synthesis of 4H-Benzo[b]Pyrans in Water: A Green Protocol. Eurasian Chem. Commun. 2020, 2, 410–419. DOI: 10.33945/SAMI/ECC.2020.3.11.
   Google Scholar
• Hosseinzadeh, Z.; Razzaghi-Asl, N.; Ramazani, A.; Aghahosseini, H.; Ramazani, A. Synthesis, Cytotoxic Assessment, and Molecular Docking Studies of 2,6-Diaryl-Substituted Pyridine and 3,4-Dihydropyrimidine-2(1H)-One Scaffolds. Turk. J. Chem. 2020, 44, 194–213. DOI: 10.3906/kim-1903-72.
   PubMed Web of Science ®Google Scholar
• Yao, C.; Yu, C.; Li, T.; Tu, S. An Efficient Synthesis of 4H-Benzo[g]Chromene-5,10-Dione Derivatives through Triethylbenzylammonium Chloride Catalyzed Multicomponent Reaction under Solvent-Free Conditions. Chin. J. Chem. 2009, 27, 1989–1994. DOI: 10.1002/cjoc.200990334.
   Web of Science ®Google Scholar
• Khan, M. N.; Pal, S.; Karamthulla, S.; Choudhury, L. H. Imidazole as Organocatalyst for Multicomponent Reactions: Diversity Oriented Synthesis of Functionalized Hetero- and Carbocycles Using in Situ-Generated Benzylidenemalononitrile Derivatives. RSC Adv. 2014, 4, 3750–3741. DOI: 10.1039/C3RA45252B.
   Web of Science ®Google Scholar
• Khorami, F.; Shaterian, H. R. Silica-Bonded Propylpiperazine-N-Sulfamic Acid as Recyclable Solid Acid Catalyst for Preparation of 2-Amino-3-Cyano-4-Aryl-5,10-Dioxo- 5,10-Dihydro-4H-Benzo[g]Chromenes and Hydroxy-Substituted Naphthalene-1,4-Dione Derivatives. Chinese J. Catal. 2014, 35, 242–246. DOI: 10.1016/S1872-2067(12)60761-X.
   Web of Science ®Google Scholar
• Khorami, F.; Shaterian, H. R. Preparation of 2-Amino-3-Cyano-4-Aryl-5,10-Dioxo-5,10-Dihydro-4H-Benzo[g]Chromene and Hydroxyl Naphthalene-1,4-Dione Derivatives. Res. Chem. Intermed. 2015, 41, 3171–3191. DOI: 10.1007/s11164-013-1423-6.
   Web of Science ®Google Scholar
• Maleki, B.; Baghayeri, M.; Sheikh, S.; Babaee, S.; Farhadi, S. One-Pot Synthesis of Some 2-Amino-4H-Chromene Derivatives Using Triethanolamine as a Novel Reusable Organocatalyst under Solvent-Free Conditions and Its Application in Electrosynthesis of Silver Nanoparticles. Russ. J. Gen. Chem. 2017, 87, 1064–1072. DOI: 10.1134/S1070363217050280.
   Web of Science ®Google Scholar
• Brahmachari, G.; Banerjee, B. Facile and One-Pot Access to Diverse and Densely Functionalized 2-Amino-3-Cyano-4H-Pyrans and Pyran-Annulated Heterocyclic Scaffolds via an Eco-Friendly Multicomponent Reaction at Room Temperature Using Urea as a Novel Organo-Catalyst. ACS Sustainable Chem. Eng. 2014, 2, 411–422. DOI: 10.1021/sc400312n.
   Web of Science ®Google Scholar
• Gong, K.; Wang, H. L.; Luo, J.; Liu, Z. L. One-Pot Synthesis of Polyfunctionalized Pyrans Catalyzed by Basic Ionic Liquid in Aqueous Media. J. Heterocyclic Chem. 2009, 46, 1145–1150. DOI: 10.1002/jhet.193.
   Web of Science ®Google Scholar
• Behbahani, F. K.; Alipour, F. One-Pot Synthesis of 2-Amino-4H-Pyrans and 2-Amino-Tetrahydro-4H-Chromenes Using L-Proline. G. U. J. Sci. 2015, 28, 387–393.
   Google Scholar
• Behbahani, F. K.; Ghorbani, M.; Sadeghpour, M.; Mirzaei, M. L-Proline as Reusable and Organo Catalyst for the One-Pot Synthesis of Substituted 2-Amino-4H-Chromenes. LOC 2013, 10, 191–194. DOI: 10.2174/1570178611310030008.
   Web of Science ®Google Scholar
• Sapkal, S. B.; Shelke, K. F.; Kategaonkar, A. H.; Shingare, M. S. Dual Role of Ammonium Acetate for Solvent-Free Synthesis of 1,3-Disubstituted-2,3-Dihydro-1H-Naphth-[1,2-e] [1,3]-Oxazine. Green Chem. Lett. Rev. 2009, 2, 57–60. DOI: 10.1080/17518250902887066.
   Web of Science ®Google Scholar
• Nongrum, R.; Nongthombam, G. S.; Kharkongor, M.; Rani, J. W. S.; Rahman, N.; Kathing, C.; Myrboh, B.; Nongkhlaw, R. A Nano-Organo Catalyzed Route towards the Efficient Synthesis of Benzo[b]Pyran Derivatives under Ultrasonic Irradiation. RSC Adv. 2016, 6, 108384–108392. DOI: 10.1039/C6RA24108E.
   Web of Science ®Google Scholar
• Behbahani, F. K.; Samaei, S. Synthesis of 2-Amino-4H-Chromenes Using Diethylamine as an Organocatalyst. Heterocycl. Lett. 2015, 5, 529–535.
   Web of Science ®Google Scholar
• Behbahani, F. K.; Mehraban, S. Synthesis of 2-Amino-3-Cyano-7-Hydroxy-4H-Chromenes Using L-Proline as a Biocatalyst. J. Korean Chem. Soc. 2015, 59, 284–288. DOI: 10.5012/jkcs.2015.59.4.284.
   Web of Science ®Google Scholar
• Behbahani, F. K.; Naderi, M. One-Pot Synthesis of 2-Amino-4H-Chromenes Catalyzed by Fe(ClO4)3/SiO2. Russ. J. Gen. Chem. 2016, 86, 2804–2806. DOI: 10.1134/S1070363216120434.
   Web of Science ®Google Scholar