An autoxidative approach to 1,2,3,4-tetrahydroisoquinolin-1-one and tetrahydro-β-carbolin-1-one

✍ Scribed by Michèle Bois-Choussy; Michaël De Paolis; Jieping Zhu

• Book ID: 104230550
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 70 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00482-8

✦ Synopsis

Treatment of N-benzyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylate with sodium hydride in N,N-dimethylformamide gives the corresponding N-benzyl 1,2,3,4-tetrahydroisoquinolin-1-one in quantitative yield. The N-benzyl 1,2,3,4-tetrahydro-b-carbolin-1-one is prepared in a similar fashion. The N-deprotection occurred concomitantly with the oxidative decarboxylation when the nitrogen was benzyloxycarbonylated.