1-Substituted β-Carbolines by a Pictet−Spengler Cyclization with Thioortho Esters and Carbon−Carbon Bond Formation via N-Sulfonyl Iminium Ions Generated from N,S-Sulfonyl Acetals
The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-β-carbolines under modified Pictet−Spengler conditions, is described. The 1-heterosubstituted β-carbolines furnished 1-substituted β-carbolines upon reaction with Grignard reagents and silyl derivatives...
Saved in:
Published in | Organic letters Vol. 7; no. 17; pp. 3701 - 3704 |
---|---|
Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
18.08.2005
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-β-carbolines under modified Pictet−Spengler conditions, is described. The 1-heterosubstituted β-carbolines furnished 1-substituted β-carbolines upon reaction with Grignard reagents and silyl derivatives under Lewis acid promotion. |
---|---|
Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol051342i |