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

Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles

“…When 2-aminobenzyl alcohol 1 is exposed to carbon monoxide 98 as a carbonylation reagent, O 2 as an oxidant and Et 3 N as a base in the presence of selenium powder as a non-metal catalyst, a series of 1,4dihydro-2H-3,1-benzoxazin-2-one 99 can be obtained as the target products (Scheme 52). [75] The carbonylation of 2-aminobenzyl alcohol was accomplished via the generation of the active COSe intermediate A from the reaction of Se and CO in the presence of a base, followed by nucleophilic attack of substrate 1 to give intermediate B. Finally, intramolecular nucleophilic addition in B gave product 99.…”

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

“…1,4-Dihydro-2H-3,1-benzoxazin-2-one shows abundant potential biological activities such as progesterone receptor antagonist, [10] HIV-1 reverse transcriptase inhibitor (Scheme 1). [11] Typical synthetical methods includes the catalytic chlorocyclization of 2vinylphenylcarbamates, [12] the selenium-catalyzed oxidative carbonylation of 2-aminobenzyl alcohol, [13] the copper(I)/N-heterocyclic carbene-catalyzed addition of terminal alkynes to trifluoromethyl ketones, [14] and the intramolecular conversion of N,N-bis (2-picolyl)ureas to cyclic carbamates. [15] 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.…”