Issue 19, 1995

Ozonolysis of (cyclohexa-1,4-dienyl)-L-alanine. An approach to the synthesis of new unnatural amino acids. X-Ray molecular structure of 2-hydroxy-7-methyl-3-phenylpyrazolo[1,5-a]pyrimidine

Abstract

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 a pyrazolyl group, as direct condensation with hydrazine was successful.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1995, 2509-2515

Ozonolysis of (cyclohexa-1,4-dienyl)-L-alanine. An approach to the synthesis of new unnatural amino acids. X-Ray molecular structure of 2-hydroxy-7-methyl-3-phenylpyrazolo[1,5-a]pyrimidine

G. Zvilichovsky and V. Gurvich, J. Chem. Soc., Perkin Trans. 1, 1995, 2509 DOI: 10.1039/P19950002509

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