13444-14-9

Usage

InChI:InChI=1/C10H9NO2/c1-2-7-11-8-5-3-4-6-9(8)13-10(11)12/h2-6H,1,7H2

Upstream product

• 59-49-4 2-Benzoxazolinone 
• 106-95-6 allyl bromide 
• 107-18-6 allyl alcohol 
• 100-65-2 N-Phenylhydroxylamine 
• 117531-28-9 N-allyl-N-(phenyl)hydroxylamine 
• 76-02-8 trifluoroacetyl chloride 
• 15022-08-9 diallylcarbonate 
• 95-55-6 2-amino-phenol 

Relevant academic research and scientific papers

The Reaction of Dialkyl Carbonates with o-Aminophenol Catalysed by K 2CO3: A Novel High-Yield Synthesis of N-Alkylbenzoxazol-2- ones

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.

Palladium-Catalyzed Dehydrative Cross-Coupling of Allylic Alcohols and N-Heterocycles Promoted by a Bicyclic Bridgehead Phosphoramidite Ligand and an Acid Additive

A mild and efficient dehydrative cross-coupling reaction between allylic alcohols and N-heterocycles using palladium catalysis is reported. A bicyclic bridgehead phosphoramidite (briphos) ligand together with Pd(dba)2 is a highly efficient catalyst, and an acid additive involved in the rate-determining step promotes the catalytic cycle. The coupling reaction of allylic alcohols with N-heterocycles including imidazoles, benzimidazoles, and triazole proceeds under mild reaction conditions with high yields using Pd/briphos and pentafluorophenol.

Synthesis of 3-alkylbenzoxazolones from N-alkyl-N-arylhydroxylamines by contiguous O-trichloroacetylation, trichloroacetoxy ortho-shift, and cyclization sequence

Benzoxazolone pharmacophore is present in clinical pharmaceuticals, drug candidates, and many compounds having a wide spectrum of biological activities. The methods available for the synthesis of benzoxazolones have limited diversity due to problems in accessibility and air-sensitivity of diversely substituted o-aminophenols from which they are generally prepared by cyclocarbonylation with phosgene or its equivalents. The present paper describes a mild method for the synthesis of 3-alkylbenzoxazolones from easily accessible and air-stable nitroarenes. Nitroarenes were converted to N-alkyl-N-arylhydroxylamines in two steps involving partial reduction to arylhydroxylamines followed by selective N-alkylation. Treatment of N-alkyl-N-arylhydroxylamines with trichloroacetyl chloride and triethylamine afforded 3-alkylbenzoxazolones generally in good yields through an uninterrupted three-step sequence involving O-trichloroacetylation, N→Cortho trichloroacetoxy shift, and cyclization in a single pot at ambient temperatures. The present method is mild, wide in scope, economical, and regioselective. Many sensitive groups like alkyl and aryl esters, amide, cyano, and the carbon-carbon double bond survive the reaction.