1-substituted beta-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 |
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| Authors: | Silveira Claudio C Felix Luciana A Braga Antonio L Kaufman Teodoro S |
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| Affiliation: | Departamento de Química, Universidade Federal de Santa Maria, 97105.900, Santa Maria, RS, Brazil. silveira@quimica.ufsm.br |
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| Abstract: | ![]()
The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-beta-carbolines under modified Pictet-Spengler conditions, is described. The 1-heterosubstituted beta-carbolines furnished 1-substituted beta-carbolines upon reaction with Grignard reagents and silyl derivatives under Lewis acid promotion. [reaction: see text] |
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