Intramolecular conversion of N,N-bis(2-picolyl)ureas to cyclic carbamates

The Reaction of o‐Aminoacetophenone N‐Tosylhydrazone and CO2 toward 1,4‐Dihydro‐2H‐3,1‐benzoxazin‐2‐ones

“…1,4‐Dihydro‐2 H ‐3,1‐benzoxazin‐2‐one shows abundant potential biological activities such as progesterone receptor antagonist, HIV‐1 reverse transcriptase inhibitor (Scheme ) . Typical synthetical methods includes the catalytic chlorocyclization of 2‐vinylphenylcarbamates, the selenium‐catalyzed oxidative carbonylation of 2‐aminobenzyl alcohol, the copper(I)/ N ‐heterocyclic carbene‐catalyzed addition of terminal alkynes to trifluoromethyl ketones, and the intramolecular conversion of N , N ‐bis(2‐picolyl)ureas to cyclic carbamates . To the best of our knowledge, example on the application of CO 2 as a C1 source to access such frameworks has never been reported so far.…”

Selenium-catalyzed oxidative carbonylation of 2-aminobenzyl alcohol to give 1,4-dihydro-2 H -3,1-benzoxazin-2-one

“…1,4-Dihydro-2H-3,1-benzoxazin-2-one is an important structural motif that can be found in a wide range of biologically active compounds. For example, efavirenz, which is a non-nucleoside reverse transcriptase inhibitor for the treatment of HIV infections, consists of a substituted 1,4-dihydro-2H-3,1-benzoxazin-2-one core [1][2][3]. Several other compounds containing this structural motif have been reported to be orally active nonsteroidal progesterone receptor antagonists, which could be used for the treatment of hormone-dependent cancers [4][5][6].…”