SYNTHESIS OF AZA-POLY-HETEROCYCLES THROUGH THE AZA-ANNELATION [3+3] OF 2,5-DIAMINO-1,4-BENZOQUINONE AGAINST DIFFERENT POLYCARBONYLATED ELECTROPHILS
enaminones, quinolones, heterocycles
In this work, the study of the reactivity of 2,5-diamino-1,4-benzoquinone against arylidenes derived from Meldrum acid, barbituric acid and 1,3-indandione in aza-ringing- [3+3] reactions was carried out for the first time, 06 new quinolinetrionic nuclei were obtained in yields between 20 and 93%, in addition to 04 new quinolinetetraonic nuclei in yields between 52 and 98%. Additionally, from the synthetic application of the 6-amino-4-phenyl-quinolinetrione obtained, it was possible to access a new benzoxazole-dihydroquinoline hybrid via oxidative cyclization reactions, promoted by Pd/C (20 mol%). In addition, the reactivity of 2,5-diamino-1,4-benzoquinone against ninhydrin was also investigated and it was possible to obtain an unprecedented pentacycle compound, with a yield of 92%. In addition, a study for the application of 5-amino-isatin in obtaining quinolinic nuclei, generated two new hybrids between isatin/quinoline with 43% and isatin/naphthoquinone with 65% yield.