Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthesis of Cyclic Peptide. I. Preparation of Cyclo-di-β-alanyl from 1,4-Cyclohexanedione
Hiroshi WatanabeShigeru KuwataSugao Koyama
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1963 Volume 36 Issue 2 Pages 143-145

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Abstract

1) By the direct Beckmann rearrangement of 1,4-cyclohexanedione dioxime by polyphosphoric acid, trifluoroacetic acid, perchloric acid or sulfuric acid at about 100°C, no expected cyclo-di-β-alanyl but p-phenylenediamine was obtained.
2) By indirect Beckmann rearrangement using di-p-tosylate of 1,4-cyclohexanedione dioxime as an intermediate, the rearrangement occurs certainly though the isolation of the cyclic dipeptide was not successful.
3) By the Schmidt reaction of 1,4-cyclohexanedione, the expected rearrangement proceeded smoothly and from the reaction products cyclo-di-β-alanyl was easily isolated.

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