A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel-Crafts reactions

被引:30
作者
Angeli, Marco [1 ]
Bandini, Marco [1 ]
Garelli, Andrea [1 ]
Piccinelli, Fabio [1 ]
Tommasi, Simona [1 ]
Umani-Ronchi, Achille [1 ]
机构
[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
关键词
D O I
10.1039/b607864h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical catalytic approach to the synthesis of 4-substituted 1,2,3,4-tetrahydro-beta-carbolines (THBCs, 1) and 1,2,3,9-tetrahydropyrano[3,4-b] indoles ( 2) via InBr3-catalyzed intramolecular Friedel - Crafts ( F - C) cyclization is described. The use of cross-metathesis reaction represents a direct route to the cyclization precursors and the use of InBr3 ( 5 mol%) allowed polycyclic indole compounds to be isolated in high yields under mild reaction conditions (rt, DCM, minutes). Finally, efforts toward the development of a stereocontrolled version of the present cyclization are presented, highlighting [salenAlCl] and bimetallic [(salenAlCl)(2) - InBr3] system as promising chiral Lewis acids (ee up to 60%).
引用
收藏
页码:3291 / 3296
页数:6
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