6- [2-furylvinyl] -1,2,4- triazinone derivatives as a source of polyfunctional mono- and biheterocycles

ABSTRACT

Reaction of 6-[2-furylvinyl]-3-thioxo- 2,3,4,5- tetrahydro-1,2,4-triazin-5-one [1] with chloroacetone gave acetonylthiotriazinone derivative [2] and thiazolotriazinone [3]. 2,4-Bis- [2-furoyl]-6-[2-furyl-vinyl] triazinone [4], 3-amino-thiazolotriazinone [5] were prepared by reaction of 1 with furoyl chloride, dibromoacetonitrile, separately. Also, compound 1 was reacted with formaldehyde to give 6 and 7. Methylthiotriazinone [8] was prepared, thereafter transferred into the hydrazinotriazinone [9]. Compound 9 was reacted with aromatic aldehydes and formic acid to give dihydrotriazolotriazinones [10a,b] and triazolo -triazineone [11], respectively. Moreover, when compound 9 was refluxed with acetic anhydride, tetrabromophthalic anhydride, the products were N, N-diacetyl triazinyl acetate [12] and triazinyltetrabromo phthalazindione [13], respectively