76293-10-2Relevant academic research and scientific papers
Intramolecular Nitrene Insertions into Aromatic and Heteroaromatic Systems. Part 7. Insertions into Electron-deficient Rings
Carde, Robert N.,Hayes, Peter C.,Jones, Gurnos,Cliff, Cynthya J.
, p. 1132 - 1142 (2007/10/02)
A number of routes to o-aminotriphenylmethanes are described, where one benzene ring, or both, carry potential ester groups.The most useful synthon is shown to be the 1,3-dioxan-2-yl substituent, and using this methyl 2-aminodiphenylmethane-4'-carboxylate (18) and dimethyl 2-aminotriphenylmethane-4',4''-dicarboxylate (28) have been prepared.The azides from these, respectively (19) and (29), on thermolysis at 200 deg C gave azepinoindoles (48) and (51), the first examples of ring expansion by an arylnitrene of benzene rings with electron-withdrawing substituents.Also reported are syntheses of 3- and 4-(2-azidobenzyl)pyridines (38) and (39), and of 2-(2-azidobenzyl)thiazole (40); decomposition of these azides gave mainly polymers.
Ring Expansion of an Electron-deficient Benzene by a Nitrene
Hayes, Peter C.,Jones, Gurnos
, p. 844 (2007/10/02)
Thermal decomposition of 4-(2-azidobenzyl)methoxycarbonylbenzene (1) and the triphenylmethyl analogue (2) gives azepinoindoles, by nitrene insertion into the electron-deficient benzene ring.
