Synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides: evaluation of antioxidant and antimicrobial activities

    Quim. Nova 2014, 37(8), 1297-1301

Synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides: evaluation of antioxidant and antimicrobial activities

Juan I. Sarmiento-Sánchez^I,*; Julio Montes-Avila^II; Adrián Ochoa-Terán^III; Francisco Delgado-Vargas^II; Victor Wilson-Corral^I; Sylvia P. Díaz-Camacho^II; Fernando García-Páez^I; Pedro Bastidas-Bastidas^IV

^IFaculty of Engineering, Autonomous University of Sinaloa, Blvd. of the Americas S/N, 80040, Campus Culiacán, Culiacán, Sinaloa, México ^IIFaculty of Chemical-Biological Sciences, Autonomous University of Sinaloa, Blvd. of the Americas S/N, 80040, Campus Culiacán, Culiacán, Sinaloa, México ^IIICentro de Graduados e Investigación en Química, Instituto Tecnológico de Tijuana, Blvd. Alberto Limón Padilla S/N, 22500, Tijuana, B.C., México ^IVLaboratorio de Análisis de Residuos de Plaguicidas, Centro de Investigación en Alimentación y Desarrollo, A.C., Unidad Culiacán, México

In this work we reported the synthesis of benzoxazine-2,4-diones derivatives and their evaluation of antioxidant and antimicrobial activities.

http://dx.doi.org/10.5935/0100-4042.20140201

http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422014000800006&lng=en&nrm=iso

  A facile one-step synthesis of 1H-benzoxazine-2,4-diones from heterocyclic anhydrides and TMSA was described. This paper determines their antimicrobial activity against nine human bacterial pathogens by the broth microdilution method; antioxidant activity by DPPH• inactivation and a ferric-reducing power assay; and toxicity by a brine shrimp, Artemia salina, assay. The 1H-benzoxazine-2,4-dione yields were in the range of 57 to 98%. The novel compound 1H-pyrazino[2,3-][1,3]oxazine-2,4-dione 4c showed the highest antioxidant capacity (DPPH 35.4% and FRAP 0.063 µmol TEs/µmol).

  Keywords: 1H-benzoxazine-2,4-dione; antimicrobial activity; antioxidant activity; toxicity.

  1H-3,1-benzoxazine-2,4-quinone   1H-[3,1]benzoxazine-2,4-dione 2H-3,1-benzoxazine-2,4(1H)-dione 1H-3,1-benzoxazine-2,4-dione 1H-3,1-benzoxazin-2,4-dion 1H-3,1-ベンゾキサジン-2,4-ジオン

 SMILES   O=C1NC2=C(C=CC=C2)C(=O)O1

Synthesis Reference(s) for 1H-3,1-benzoxazine-2,4-quinone

Organic Syntheses, Coll. Vol. 3, p. 488, 1955 The Journal of Organic Chemistry, 48, p. 2, 1983

1H-3,1-benzoxazine-2,4-quinone (4a). (For full characterization see lit.);^28,29 CAS number: 118-48-9; yield 85%; white solid; R_f 0.58 (petroleum ether/EtOAc 1:1 v/v);

  ¹H-NMR (200 MHz, DMSO-d₆): δ 11.74 (br s, 1H), 7.91 (dd, J₁=8.07, J₂=1.1 Hz, 1H), 7.74 (td, J₁=7.79, J₂=1.28 Hz, 1H), 7.25 (m, 2H); 

¹³C-NMR (50 MHz, DMSO-d₆): δ 159.9, 147.1, 141.4, 136.9, 128.9, 123.5, 115.3; 

CG-MS m/z: 164 [M+H]⁺


                   



 Centro de Investigación en Alimentación y Desarrollo


 


        


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 University of Sinaloa

1. 1. 

   




 Instituto Tecnológico de Tijuana