1168-15-6Relevant articles and documents
4-Azidoquinoline N-oxide: Synthesis and photolysis
Shaforost,Ryzhakov,Rodina
, p. 728 - 730 (2008)
In photolysis of 4-azidoquinoline N-oxide azoxy compound was isolated as the final reaction product. This result may be ascribed to the dimerization of the intermediate nitrene to azo compound followed by oxidation of the latter with air oxygen. The initially arising nitrene is stabilized by resonance conjugation involving the aromatic system and the N-oxide group. The rate constants of 4-azidoquinoline N-oxide photolysis were measured in various solvents and the values of spin density and bond lengths in the formed nitrene were calculated.
Concerning Model Metabolites of the Carcinogen 4-Nitroquinoline 1-Oxide. Reactivity of 1-Acetoxy-4-(hydroxyimino)-1,4-dihydroquinoline
Demeunynck, Martine,Tohme, Najat,Lhomme, Marie-France,Mellor, John M.,Lhomme, Jean
, p. 405 - 410 (2007/10/02)
1-Acetoxy-4-(hydroxyimino)-1,4-dihydroquinoline is obtained by hydrolysis of 1-acetoxy-4-(acetoxyimino)-1,4-dihydroquinoline under strongly acidic conditions.At pH 1 the monoacetate is protonated and on hydrolysis affords only 1-hydroxy-4-(hydroxyimino)-1,4-dihydroquinoline.Above pH 1 on hydrolysis the monoacetate affords a complex product mixture including 4-(hydroxyamino)quinoline and 4-nitrosoquinoline.Comparison of the above behavior of 1-acetoxy-4-(hydroxyamino)-1,4-dihydroquinoline with that of 1-hydroxy-4-(acetoxyimino)-1,4-dihydroquinoline at a neutral pH suggests that the former type of ester is less likely to be important in those steps initiating oncogenesis.In contrast the latter type of monoester or diesters corresponding to 1-acetoxy-4-(acetoxyimino)-1,4-dihydroquinoline by their ability to generate nitrenium ion intermediates and undergo attack by nucleophiles at the 3-position are likely intermediates in the process of oncogenesis.Further aspects of their likely biological role are discussed.
Polarization of heterocyclic rings with aromatic character. CXVIII. 4-Hydroxyaminoquinoline-N-oxide.
OCHIAI,OHTA,NOMURA
, p. 310 - 313 (2007/10/04)
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