30741-06-1Relevant academic research and scientific papers
Electrogenerated N-heterocyclic carbenes: N-functionalization of benzoxazolones
Chiarotto,Feroci,Orsini,Sotgiu,Inesi
experimental part, p. 3704 - 3710 (2009/09/05)
A simple electrochemical procedure for the N-acylation and N-alkylation of benzoxazol-2(3H)-ones has been set up via electrolysis of an ionic liquid containing a benzoxazolone followed by addition of saturated or unsaturated anhydrides or alkyl halides. The electrochemically induced N-functionalization of benzoxazol-2(3H)-ones works very well in all tested ionic liquids, avoiding the use of volatile organic solvents. The N-acyl and N-alkyl derivatives of benzoxazol-2(3H)-ones were isolated in good to excellent yields; moreover, the ionic liquid has been reused fivefold maintaining the high yield of the products.
The Reaction of Dialkyl Carbonates with o-Aminophenol Catalysed by K 2CO3: A Novel High-Yield Synthesis of N-Alkylbenzoxazol-2- ones
Selva, Maurizio
, p. 2872 - 2876 (2007/10/03)
At 130-150°C and in the presence of catalytic K2CO 3, o-aminophenol (1) readily reacts with dialkyl carbonates (2: ROCO2R; 2a: R = Me, 2b: Et, 2c: Allyl, 2d: Bn) to give the corresponding N-alkylbenzoxazol-2-ones (3a-d) in high yields (88-98%). This reaction is a rare example where dialkyl carbonates may simultaneously act as carbonylating and alkylating agents likely through a BAc2/B A12 sequence. Moreover, compounds 2a-c serve also as solvents. In the case of 2d, 1,2-dimethoxyethane (DME) is the reaction medium.
