New synthesis of isoquinoline and 3,4-dihydroisoquinoline derivatives

作者：Kobayashi Kazuhiro^*; Shiokawa Taiyo; Omote Hiroki; Hashimoto Kenichi; Morikawa Osamu; Konishi Hisatoshi

来源：Bulletin of the Chemical Society of Japan, 2006, 79(7): 1126-1132.

DOI：10.1246/bcsj.79.1126

A simple and efficient synthesis of isoquinoline and 3,4-dihydroisoquinoline derivatives is described. I-Alkyl(or aryl)isoquinoline and 1-isoquinolinamine derivatives were obtained by intramolecular cyclization of 2-(2-methoxyethenyl)benzonitriles initiated by the addition of alkyl(or aryl)lithiums and lithium dialkylamides to the nitrile carbons, respectively. Synthesis of 4-aryl-3,4-dihydroisoquinolines was achieved by reactions of 2-(1-arylethenyl)benzonitriles with organolithiums, followed by aqueous workup. Treatment of the reaction mixtures with electrophiles prior to aqueous workup allowed the synthesis of 4,4-disubstituted 3,4-dihydroisoquinolines.

• 出版日期2006-7-15