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DOI: 10.1039/A705364I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 3581-3586

Pyrolysis of 1-substituted pyrazoles and chloroform at 550 °C: formation of α-carboline from 1-benzylpyrazoles

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Inayat A. Bhatti, Reginald E. Busby, Murtedza bin Mohamed, John Parrick and C. J. Granville Shaw

Abstract

Pyrolysis of 13CH3 labelled 1-methylpyrazole 8 with chloroform at 550 °C in a continuous flow reactor yields unlabelled 2-chloropyrimidine 9 and 2-cyanopyrrole 10 labelled at the cyano group. However, pyrolysis of 1-benzylpyrazole 14 with chloroform under similar conditions gives 9, 2-phenylpyrimidine 13 and, as the major product, α-carboline 15. Pyrolysis of several substituted 1-(arylmethyl)pyrazoles and the use of 13C and 15N labelled compounds provides direct evidence by which the positions of 7 atoms of 1-benzylpyrazole can be located in the α-carboline. These data support the mechanisms suggested for the formation of 9, 10, and 15.

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