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A reacao de ciclizacao termica de o-halobenzilideno barbituratos foi desenvolvida como um simples e eficiente metodo para a preparacao de oxadeazaflavinas. A utilizacao de condicoes de reacao em estado solido com irradiacao de microondas forneceu os produtos em 5 min e com rendimentos entre 47 e 98%. Os resultados experimentais das sinteses e a analise termogravimetrica das reacoes concordam com os resultados da simulacao do mecanismo por modelagem molecular, indicando que a reacao ocorre atraves de uma ciclizacao hetero-Diels-Alder intra-molecular, seguida por um processo rapido de re-aromatizacao. The thermal cyclization reaction of o-halobenzylidene barbiturates was developed as an efficient and simple method for the preparation of oxadeazaflavines. The use of solid state reaction conditions with microwave irradiation afforded the products in 5 min with 47 to 98% yield. Experimental synthetic results and thermogravimetric reaction analyses agree with the molecular modeling mechanism simulation, indicating that this reaction occurs through an intramolecular hetero-Diels-Alder cyclization followed by fast re-aromatization.

Synthesis and mechanism of formation of oxadeazaflavines by microwave thermal cyclization of ortho-halobenzylidene barbiturates