Abstract
Background: Chromenes and pyran annulated heterocycles are the most common frameworks existing in various biologically active molecules. Due to their beneficial and biological properties, they are eyecatching synthetic targets in the arsenal of organic chemistry. Thus, finding green and efficient methods, as well as searching for a new catalyst for the synthesis of these heterocycles is of interest to organic chemistry researchers.
Objective: Sodium malonate as a readily available catalyst was employed aimed at the multicomponent synthesis of numerous 2-amino-4H-chromenes and 2-amino-4H-pyrans in water as a green medium reaction.
Methods: The reaction was performed via treatment of aldehydes (1 mmol) with malononitrile/ethyl cyanoacetate (1 mmol) and β-dicarbonyl compounds (1 mmol)/or resorcinol (1 mmol) in water (4 mL) in the presence of sodium malonate (10 mol %) at 70°C. On completion of the reaction (monitored by TLC analysis), the reaction mixture was gradually cooled at room temperature, and the resulting precipitates were collected by filtration, washed with cold ethanol and air-dried to give the corresponding pure products. The solvent was evaporated from the filtrate to recover the catalyst, and the catalyst was reused for subsequent reactions.
Results: In the initial stages, we explored the best reaction conditions using three-component reaction of benzaldehyde, malononitrile, and dimedone as the model reaction. The effects of catalyst loading, temperature, and solvents were explored for this reaction. It was found that the best results were obtained for the synthesis of 2-amino-4H-chromenes and 2-amino-4H-pyran when the three-component reaction was carried out with equivalent molar quantities of each of the reactants in water containing 10 mol% sodium malonate at 70°C for 15 min in 96% yield. After finding optimal conditions, these conditions apply to other reactants and the target heterocyclic products were obtained with excellent yields.
Conclusion: This study describes an efficient, environmentally benign, and clean one-pot, three-component synthesis of 2-amino-4H-chromenes and 2-amino-4H-pyran-3-carboxylates in the presence of sodium malonate as the commercially available catalyst in an aqueous medium at 70°C. High yields, mild reaction conditions, relatively shorter reaction times, use of simple reagents, and no requirement of the ultrasound, microwave, and ball milling techniques are the salient features and benefits of the present method. In addition, the present process is smooth and green.
Keywords: 2-Amino-4H-chromene, 2-amino-4H-pyran-3-carboxylate, dimedone, nitrile-containing compounds, resorcinol, sodium malonate.
Graphical Abstract
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[http://dx.doi.org/10.1080/10406638.2018.1454968]
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[http://dx.doi.org/10.1080/10406638.2018.1454968]
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(g) Kiyani, H.; Aslanpour, S. Synthesis of Erlenmeyer-Plöchl azlactones promoted by 5-sulfosalicylic acid. Heterocycles, 2017, 94(7), 1314-1321.
(h) Mosallanezhad, A.; Kiyani, H. KI-Mediated three-component reaction of hydroxylamine hydrochloride with aryl/heteroaryl aldehydes and two β-oxoesters. Orbital: Electron. J. Chem, 2018, 10(2), 133-139.
(i) Kiyani, H.; Mosallanezhad, A. Sulfanilic acid-catalyzed synthesis of 4-arylidene-3-substituted isoxazole-5(4H)-ones. Curr. Org. Synth., 2018, 15(5), 715-772.
(b) Biswas, K.; Ghosh, S.; Ghosh, P.; Basu, B. Cyclic ammonium salts of dithiocarbamic acid: stable alternative reagents for the synthesis of S-alkyl carbodithioates from organyl thiocyanates in water. J. Sulfur Chem., 2016, 37(4), 361-376.
(c) Kiyani, H.; Tazari, M. Aqua one-pot, three-component synthesis of dihydropyrano[3,2-c]chromenes and amino-benzochromenes catalyzed by sodium malonate. Res. Chem. Intermed., 2017, 43(11), 6639-6650.
(d) Kumaravel, K.; Vasuki, G. Multi-component reactions in water. Curr. Org. Chem., 2009, 13(18), 1820-1841.
(e) Kiyani, H.; Bamdad, M. Sodium ascorbate as an expedient catalyst for green synthesis of polysubstituted 5-aminopyrazole-4-carbonitriles and 6-amino-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles. Res. Chem. Intermed., 2018, 44(44), 2761-2788.
(f) Kiyani, H.; Aslanpour, S. Sulfanilic acid-catalyzed green synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones. Heterocycles, 2018, 96(2), 297-303.
(g) Kiyani, H.; Aslanpour, S. Synthesis of Erlenmeyer-Plöchl azlactones promoted by 5-sulfosalicylic acid. Heterocycles, 2017, 94(7), 1314-1321.
(h) Mosallanezhad, A.; Kiyani, H. KI-Mediated three-component reaction of hydroxylamine hydrochloride with aryl/heteroaryl aldehydes and two β-oxoesters. Orbital: Electron. J. Chem, 2018, 10(2), 133-139.
(i) Kiyani, H.; Mosallanezhad, A. Sulfanilic acid-catalyzed synthesis of 4-arylidene-3-substituted isoxazole-5(4H)-ones. Curr. Org. Synth., 2018, 15(5), 715-772.
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Devi, I.; Bhuyan, P.J. Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions. Tetrahedron Lett., 2004, 45(47), 8625-8627.
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