A one-step route to 4-hydroxy-2,3-diaryl-3,4-dihydro-1 (2H)-isoquinolones

✍ Scribed by David J. Dodsworth; María-Pía Caliagno; Ursula E. Ehrmann; Peter G. Sammes

• Publisher: Elsevier Science
• Year: 1980
• Tongue: French
• Weight: 206 KB
• Volume: 21
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71138-5

✦ Synopsis

A new procedure for the synthesis of 2,3-diaryl-3,4-dihydro-4-hydroxy-1(2H)isoquinolones is described rn which the cis-isomer predominates. Dehydration leads to 2,4-diarylisocarbostyrils.

The synthetic utility of metallated phthalide derivatives has recently received considerable attention for the preparation of polycyclic systems such as quinones, naphthols, and anthraquinones.

l-3 In these procedures, the use of substituted phthalides and substrates permits the regioselective formation of products, under mild conditions, in moderate to good yields.

Herein we describe the reaction of lithium phthalides with Schiff's bases, which results in the formation of isoquinolones.

Recently reports on alternative methods for generating these and related systems have appeared. 4,s