Isolation and Structural Investigation of the Chromophore in the Fujiwara Reaction as Applied to Chloramphenicol

KAZUO OKUMURA; YOSHIHIRO KURODA; TOYOZO UNO

doi:10.1248/cpb.31.2737

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363

Isolation and Structural Investigation of the Chromophore in the Fujiwara Reaction as Applied to Chloramphenicol

KAZUO OKUMURA, YOSHIHIRO KURODA, TOYOZO UNO

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Keywords: ^<13>C NMR spectrum

JOURNAL FREE ACCESS

1983 Volume 31 Issue 8 Pages 2737-2742

DOI https://doi.org/10.1248/cpb.31.2737

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Abstract

The structure of a red chromogen which is produced by applying the Fujiwara reaction to chloramphenicol was determined by means of NMR, mass spectroscopy and reasonance Raman spectroscopy. The red product was identified as 5-hydroxymethyl-4-(4-nitrobenzeno)-2, 3-pyrrolidindione. This compound is different from the nitrogenated polyene which is produced in the Fujiwara reaction applied to such gem-trichloro compounds as chloroform and benzotrichloride.

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