Synthesis of 7-Substituted 6,7-Dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones. Reaction of 7-Hydroxy Derivatives with Nucleophiles

Abstract

Various 7-substituted 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones are synthesized by the reaction of the corresponding 7-hydroxy derivatives with nucleophiles involving active methylene compounds, aromatics, alcohols, p-toluenethiol, benzenesulfinic acid, triethyl phosphite, ammonia, and amines under acidic or basic conditions. Some synthetic applications of the products obtained are demonstrated to give a 7-methylene derivative and fused tricyclic derivatives.

Synthesis of Phosphonic Acids Possessing Isoindolin-1-one Moiety: Unexpected Acid-Catalyzed C-P-Bond Cleavage

“…21 A mixture of 2-benzyl-3-hydroxy-isoindolin-1-one 17 (0.83 g, 3 mmol) and trifluoroacetic anhydride (3 mL) was stirred for 1 h under argon. After the excess trifluoroacetic anhydride and the resulting trifluoroacetic acid were removed under reduced pressure, triethyl phosphite (1.04 mL, 6 mmol) in 10 mL of anhydrous chloroform was added to the residue, and the resulting mixture was stirred for 4 h. The reaction mixture was quenched with aqueous NaHCO 3 (saturated, 50 mL).…”