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...

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Bibliographic Details
Published inOrganic letters Vol. 7; no. 17; pp. 3701 - 3704
Main Authors Silveira, Claudio C, Felix, Luciana A, Braga, Antonio L, Kaufman, Teodoro S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.08.2005
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NUCLEOPHILES
AZALACTONES
ORGANIC-SYNTHESIS
ETHERS
TETRAHYDROISOQUINOLINES
FUSED HETEROCYCLES
1,2,3,4-TETRAHYDROISOQUINOLINES
CONDENSATION
STABILIZED CARBENIUM IONS
AUXILIARY
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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
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol051342i