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

页码：253 / 257

页数：5

共 16 条

[1]

BHATTACHARYYA S, 1994, SYNLETT, P1029

[2]

BHATTACHARYYA S, 1995, SYNLETT, P1079

[3] REDUCTIVE ALKYLATIONS OF DIMETHYLAMINE USING TITANIUM(IV) ISOPROPOXIDE AND SODIUM-BOROHYDRIDE - AN EFFICIENT, SAFE, AND CONVENIENT METHOD FOR THE SYNTHESIS OF N,N-DIMETHYLATED TERTIARY-AMINES [J].