Electrophilic amination of 2-azadienes
2-Azadienes 1 bearing a trialkylsilyloxy group on position 3 can be regarded as carboxylic acid synthons. Their cycloadditions with several classes of nitroso compounds have been studied in detail as well as the transformation of the adducts into α-amino acids. The study showed that arylnitroso comp...
| Main Authors: | , |
|---|---|
| Format: | Journal article |
| Published: |
1996
|
| Summary: | 2-Azadienes 1 bearing a trialkylsilyloxy group on position 3 can be regarded as carboxylic acid synthons. Their cycloadditions with several classes of nitroso compounds have been studied in detail as well as the transformation of the adducts into α-amino acids. The study showed that arylnitroso compounds such as nitrosobenzene reacted with 2-azadienes to give adducts that are potential precursors of α-N-arylamino acids. We have outlined an important limitation to the use of α-chloronitroso compounds. They are not compatible with highly functionalized dienes like 2-azadienes. On the other hand α-cyanonitroso and acylnitroso compounds reacted with azadienes to give adducts which were readily converted into α-amino acid derivatives. |
|---|