Journal of the Chemical Society. Perkin transactions I p. 1132 - 1142 (1981)
Update date:2022-08-03
Topics:
Carde, Robert N.
Hayes, Peter C.
Jones, Gurnos
Cliff, Cynthya J.
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.
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Doi:10.1016/S0022-1139(00)81290-7
(1981)Doi:10.1007/BF00505682
(1981)Doi:10.1246/cl.1982.813
(1982)Doi:10.1016/S0040-4039(01)92896-5
(1981)Doi:10.1021/ja00408a023
(1981)Doi:10.1021/ja01265a024
(1939)
