Pyrrolo[1,2-a][1,3,5]triazine-2,4(1H,3H)-diones. Part I. Synthesis from 1,3,5-triazine-2,4(1H,3H)-diones
Abstract
Reaction of ethyl bromopyruvate (4) with 6-methyl-(2) and 6-benzyl-1,3,5-triazine-2,4(1H,3H)-diones (3) gave moderate yields of 1,2,3,4-tetrahydro-2,4-dioxopyrrolo[1,2-a][1,3,5]triazine-7-carboxylate esters, (10) and (11), respectively. Other bromocarbonyl compounds failed to react or gave low yields of product. Pyrrolo[1,2-a]-[1,3,5]triazine-2,4(1H,3H)-dione (14) has been synthesised from the 7-ester and a bromination is shown to yield 8-mono-(17) and 6,8-di-bromo-derivatives (18). 6-Methyl-1,3-diphenacyl-1,3,5-triazine-2,4(1H,3H)-dione (19) yields 3-phenacyl-7-phenylpyrrolo[1,2-a][1,3,5]triazine-2,4(1H,3H)-dione (20) with acetic acid.