Lite Version|Standard version

To gain access to this content please
Log in via your home Institution.
Log in with your member or subscriber username and password.
Download

An intramolecular C–O insertion of 2-(2-arylamidophenyl)-2-diazoacetate has been achieved using a catalytic amount of copper triflate under mild conditions to produce 2-aryl-4H-benzo[d][1,3]oxazine-4-carboxylate in good yields. In addition, 2-diazo-2-(2-arylthioamidophenyl)acetate affords the corresponding 2-aryl-4H-benzo[d][1,3]thiazine derivatives under similar conditions. This is the first example of the synthesis of benzoxazines and benzothiazines from ortho-amidophenyl diazoacetate and ortho-thioamidophenyl diazoacetate, respectively.

Graphical abstract: Intramolecular C–O/C–S bond insertion of α-diazoesters for the synthesis of 2-aryl-4H-benzo[d][1,3]oxazine and 2-aryl-4H-benzo[d][1,3]thiazine derivatives

Page: ^ Top