A One-Pot Synthesis of 1,2-Dihydroisoquinoline Derivatives from Isoquinoline via a Four-Component Reaction

✍ Scribed by Abdolali Alizadeh; Nasrin Zohreh

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: German
• Weight: 168 KB
• Volume: 91
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200890087

✦ Synopsis

Abstract

A four‐component reaction for the synthesis of 1,2‐dihydroisoquinoline derivatives is described. The Huisgen 1,4‐dipolar intermediate, which is produced from isoquinoline and an electron‐deficient acetylene compound 1, reacts with H~2~O in the presence of diketene to produce 1,2‐dihydroisoquinoline derivatives 2 (Scheme 1). In addition, reaction of isoquinoline, dibenzoylacetylene (=1,4‐diphenylbut‐2‐yne‐1,4‐dione), and diketene in the presence of H~2~O leads to pyrroloisoquinoline derivative 7. The structures of the compounds 2a–f and 7 were corroborated spectroscopically (IR, ^1^H‐ and ^13^C‐NMR, EI‐MS) and by elemental analyses. A plausible mechanism for the reaction is proposed (Schemes 2 and 3).