Reaction #66923

Reaction equation

intermediate ( 150 )

N-(6-Acetyl-1,3-benzodioxol-5-yl)naphthalene-1-carboxamide

NaOH

→

2-(1-Naphthalenyl)-6,7-methylenedioxyquinolin-4-one

Solvents

dioxane

Conditions

Procedure

The synthetic procedure of target compounds 153 is illustrated in Scheme 11. The starting 2-amino-4,5-methylenedioxy-acetophenone (148) was first reacted with naphthalene-1-carbonyl chloride (149) to give N-(6-Acetyl-1,3-benzodioxol-5-yl)naphthalene-1-carboxamide (150). Then, the intermediate (150) was subjected to cyclization in dioxane, in the presence of NaOH, to afford 2-(1-Naphthalenyl)-6,7-methylenedioxyquinolin-4-one (151). Compound 151 was first reacted with tetrabenzylpyrophosphate in THF, in the presence of NaH, to yield Dibenzyl 2-(1-naphthalenyl)-6,7-methylenedioxyquinolin-4-yl Phosphate (152). Compound 152 was then subjected to catalytic hydrogenation in MeOH to give its diphosphoric acid (153).

Source