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Rapid Synthesis and Antiviral Activity of (Quinazolin-4-Ylamino)Methyl-Phosphonates Through Microwave Irradiation
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering/Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, Guangzhou, China
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Received: 31 March 2012; in revised form: 8 May 2012 / Accepted: 8 May 2012 / Published: 1 June 2012
Abstract: This study describes the simple synthesis of new (quinazolin-4-ylamino) methylphosphonates via microwave irradiation. Substituted-2-aminobenzonitrile reacted with 1,1-dimethoxy-N,N-dimethylmethanamine at a reflux condition to obtain N'-(substituted-2-cyanophenyl)-N,N-dimethylformamidine (1). The subsequent reaction of this intermediate product with α-aminophosphonate (2) in a solution containing glacial acetic acid in 2-propanol through microwave irradiation resulted in the formation of (quinazolin-4-ylamino)methyl-phosphonate derivatives 3a to 3x, which were unequivocally characterized by the spectral data and elemental analysis. The influence of the reaction conditions on the yield of 3a was investigated to optimize the synthetic conditions. The relative optimal conditions for the synthesis of 3a include a 1:1 molar ratio of N’-(2-cyanophenyl)-N,N-dimethylformamidine to diethyl amino(phenyl)methylphosphonate and a 4:1 volume ratio of isopropanol to HOAc in the solvent mixture, at a reaction temperature of 150 °C, with a microwave power of 100 W and a corresponding pressure of 150 psi for 20 min in the microwave synthesizer. The yield of 3a was approximately 79%, whereas those of 3b to 3x were approximately 77% to 86%. Some of the synthesized compounds displayed weak to good anti-Tobacco mosaic virus (TMV) activity.
Keywords: quinazoline derivatives; α-aminophosphonate moiety; synthesis; microwave irradiation
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MDPI and ACS Style
Luo, H.; Hu, D.; Wu, J.; He, M.; Jin, L.; Yang, S.; Song, B. Rapid Synthesis and Antiviral Activity of (Quinazolin-4-Ylamino)Methyl-Phosphonates Through Microwave Irradiation. Int. J. Mol. Sci. 2012, 13, 6730-6746.
Luo H, Hu D, Wu J, He M, Jin L, Yang S, Song B. Rapid Synthesis and Antiviral Activity of (Quinazolin-4-Ylamino)Methyl-Phosphonates Through Microwave Irradiation. International Journal of Molecular Sciences. 2012; 13(6):6730-6746.
Luo, Hui; Hu, Deyu; Wu, Jian; He, Ming; Jin, Linhong; Yang, Song; Song, Baoan. 2012. "Rapid Synthesis and Antiviral Activity of (Quinazolin-4-Ylamino)Methyl-Phosphonates Through Microwave Irradiation." Int. J. Mol. Sci. 13, no. 6: 6730-6746.