Thermally induced fragmentation and cyclisation of  C ‐azidohydrazones | Zendy

Bruché Luca | Zendy; Garanti Luisa | Zendy; Zecchi Gaetano | Zendy

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Thermally induced fragmentation and cyclisation of C ‐azidohydrazones

Author(s) -

Bruché Luca,

Garanti Luisa,

Zecchi Gaetano

Publication year - 1989

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570260320

Subject(s) - chemistry , fragmentation (computing) , thermal decomposition , nitrene , benzene , boiling , hydrogen atom abstraction , hydrogen , ring (chemistry) , decomposition , photochemistry , medicinal chemistry , organic chemistry , catalysis , computer science , operating system

C ‐Azidohydrazones 2 were synthesized from the corresponding C ‐chlorohydrazones 1 and submitted to thermal decomposition in boiling benzene. Various kinds of products were obtained due to competitive modes of evolution of first‐formed nitrenes 13 , namely hydrogen abstraction to form aminohydrazones 3 and benzotriazepine 8 , and radical fragmentation to give ultimatively diaryls 4 and arylglyoxylate arylhydrazones 5 . Ring‐closed products, namely 1, 2, 4‐triazoles 6 and imidazolones 7 were also formed.

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