Marie-Thérèse Le Bris
Mar 1, 1984
Citations
0
Influential Citations
14
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
l'amino-5 nitro-2 phenol reagit avec les acides et les esters α-cetoniques en conduisant, soit a des composes heterocycliques (benzoxazinone, benzoxazoline), soit a des composes non cyclises: imines, amides. Le diamino-2,5 phenol, avec les memes reactifs, donne exclusivement les amino-7 benzoxazines-1,4 ones-2 tres fluorescentes et stables en solution dans les solvents organiques, a l'exclusion de l'ethanol. Our objective was the prepartion of flurorescent dyes in the 1,4-benzoxazinone series; accordingly, reactions of α-ketoacids and esters with 2-amino-5-nitrophenol and 5,5-diaminophenol were investigated. With 2-amino-5-nitrophenol, ethyl pyruvate yields the anil 7, which, after reduction, was cyclised into the aminobenzoxazione 5a. Benzoylformic acid leads to a mixture of 7-nitro3-phenyl-1,4-benzoxazine-2-one (6b), and hydroxy-2-nitro-4-anilinium benzoylformate (9). Glyoxylic acid reacts with 2 moles of 2-amino-5-nitrophenol, and the benzoxazoline 11 is obtained. With the αketoacids, diaminophenol leads to 7-aminobenzoxazinoes 5a-c; in these compounds, the amino group reacitivity is weakened, however, their acylation was easily performed. The organic solutions of amines 5 exhibit a high mesomeric forms 5 and 5′, occuring in this type of molwecule, as well as in many recent laser dyes, aminocoumarines for example. The stability of these solutions is quite good, except for alcoholic solutions. In this xase it was not possible to determine the structure of the resulting compound.