76943-58-3Relevant academic research and scientific papers
The Pyrolysis of 2-Azidobenzoates. A New Synthesis of Carbazoles and Other N-Heterocycles
Clancy, Michael G.,Hesabi, Massoud M.,Meth-Cohn, Otto
, p. 429 - 434 (2007/10/02)
The spray pyrolysis of aryl 2-azidobenzoates yields carbazoles, involving a rearrangement whereby the nitrogen of the product is attached to the aryl 1-carbon, a process involving a spiro 6-membered intermediate.When the aryl ortho-positions were both alkyl substituted the product was ab acridan instead.With an ortho-carboxylate, acridone formation competed with that of carbazole.When the CO-O group of the substrate was replaced by O-CO, CO-S, CO-NPh, or SO2-O the pyrolysis was ineffective.Benzyl 2-azidobenzoates, however, pyrolysed to yield 1-benzyl-2,1-benzisoxazolones by an unprecedented C-O insertion reaction of the intermediate nitrene.
Arylnitrene Cyclisations by Way of 6-Membered Spiro Intermediates. The Formation of Carbazoles, Acridines, and Acridones from Aryl 2-Azidobenzoates
Clancy, Michael G.,Hesabi, Masoud M.,Meth-Cohn, Otto
, p. 1112 - 1113 (2007/10/02)
Aryl 2-azidobenzoates undergo vapour-phase pyrolysis to give carbazoles in moderate yield: alternatively, 4-methylacridan and acridone are formed from 2,6-dimethylphenyl and salicyl 2-azidobenzoates respectively, all the products being derived from 6-membered spirobenzoxazinone intermediates.
