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- W2024966097 abstract "A general and simple approach for the synthesis of N-hydroxy and N-alkoxytryptophan and tryptamine derivatives is presented. Key-intermediates are nitro compounds which are easily accessible from gramine (16) and RCH2N2. Reduction with Al-amalgam gave in high yields the corresponding hydroxylamines. The N-alkoxy derivatives are accesible by a regioselective O-alkylation of oxime 12 followed by a reduction with borane-trimethylamine complex. The influence of the substituents R1-R3 on the reactivity and the relative stereochemistry in the Pictet-Spengler condensation with aldehydes (R4CHO) has been studied. The increased electrophilic character of the C=N double bond in the intermediate 38 due to the oxygen substituent on the nitrogen increases the reactivity and alters the stereoselectivity." @default.
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- W2024966097 date "1990-01-01" @default.
- W2024966097 modified "2023-10-03" @default.
- W2024966097 title "Syntheses of 1,3-disubstituted N-oxy-β-carbolines by the Pictet-Spengler reactions of N-oxy-tryptophan and -tryptamine derivatives" @default.
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- W2024966097 doi "https://doi.org/10.1016/s0040-4020(01)81366-1" @default.
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