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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.