A convenient synthesis of 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines via Pictet-Spengler reaction using titanium(IV) isopropoxide and acetic-formic anhydride

被引：37
|
作者：
Horiguchi, Y [1 ]
Kodama, H [1 ]
Nakamura, M [1 ]
Yoshimura, T [1 ]
Hanezi, K [1 ]
Hamada, H [1 ]
Saitoh, T [1 ]
Sano, T [1 ]
机构：
[1] Showa Pharmaceut Univ, Machida, Tokyo 1948543, Japan
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 2002年 / 50卷 / 02期
关键词：
Pictet-Spengler reaction; titanium(IV) isopropoxide; 1,2,3,4-tetrahydroisoquinoline; N-formylation; acyliminium ion;
D O I：
10.1248/cpb.50.253
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A synthesis of 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines (6) was achieved in a highly efficient manner via Pictet-Spengler reaction of arylethylamines (1) and acyclic and cyclic ketones (2) using titanium (IV) isopropoxide and acetic-formic anhydride. The cyclization of the in situ formed acyliminium ion (4) to N-formyl 1,2,3,4-tetrahydroisoquinoline (5) was greatly facilitated by using trifluoroacetic acid as an additional reagent. The Pictet-Spengler reaction was carried out by one pot procedure, providing a convenient and effective method for preparing various 1,2,3,4-tetrahydroisoquinolines.
引用
收藏
页码：253 / 257
页数：5
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