Journal of the Chemical Society. Perkin transactions I p. 2509 - 2516 (1995)
Update date:2022-08-05
Topics:
Zvilichovsky, Gury
Gurvich, Vadim
The aromatic ring in L-phenylalanine was transformed into isoxazolyl, N-phenylpyrazolyl, and the bicyclic pyrazolo<1,5-a>pyrimidinyl groups, by a combination of Birch reduction and ozonolysis, followed by condensation with the relevant binucleophiles.The ozonolysis was carried out on the N-acylated esters of cyclohexa-1,4-dienylalanine.The resulting N-acylated esters of heterocyclic alanine derivatives were obtained without isolation of the ozonolysis products. 4-Phenylpyrazolidine-3,5-dione was used as a 'hydrazine donor' in the construction of pyrazolyl group, as direct condensation with hydrazine was successful.
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