5516-26-7Relevant academic research and scientific papers
Facile Protocols towards C2-Arylated Benzoxazoles using Fe(III)-Catalyzed C(sp 2 -H) Functionalization and Metal-Free Domino Approach
Vodnala, Nagaraju,Gujjarappa, Raghuram,Kabi, Arup K.,Kumar, Mohan,Beifuss, Uwe,Malakar, Chandi C.
supporting information, p. 1469 - 1478 (2018/05/25)
Considering their growing attention in the field of medicinal chemistry and drug-discovery research, the facile and convenient approaches towards the preparation of 2-aryl benzoxazole derivatives have been described. The transformation is accomplished by using Fe(III)-catalyzed C-H activation of benzoxazoles with boronic acids to obtain a wide range of C2-arylated benzoxazoles in high yields. The developed method excludes the formation of self-coupling compounds as side products. On the other hand, the synthesis of the products is also achieved via a metal-free domino protocol by the reaction between 1-nitroso-2-naphthol and acetophenones using catalytic amounts of CBr 4 in the presence of Cs 2 CO 3 as base. The devised tandem method avoids the use of pre-activated α-haloketones as substrates. Due to their immense impact in marketed drugs and molecules under clinical trial, the described method can be a powerful tool for their synthesis which restricts the use of precious metals as catalyst.
Reaction of 1-nitroso-2-naphthols with α-functionalized ketones and related compounds: The unexpected formation of decarbonylated 2-substituted naphtho[1,2-d][1,3]oxazoles
Aljaar, Nayyef,Malakar, Chandi C.,Conrad, Ju Rgen,Frey, Wolfgang,Beifuss, Uwe
, p. 154 - 166 (2013/03/28)
Reactions between 1-nitroso-2-naphthols and α-functionalized ketones such as α-bromo-, α-chloro-, α-mesyloxy-, α-tosyloxy-, and α-hydroxy ketones under basic conditions delivered 2-substituted naphtho[1,2-d][1,3]oxazoles in a single synthetic operation. T
Unexpected reactivity of o-nitrosophenol with RCH2Br: C-H bond cleavage and annulation to benzoxazoles and benzoxazines (R = Alkynyl)
Yao, Wei,Huang, Dejian
supporting information; experimental part, p. 736 - 738 (2010/04/05)
A one-pot reaction between two molecules of 5-diethylamino-2-nitrosophenol with one molecule of 2-butynyl bromide gave rise to a new heterocyclic compound (structure shown above) consisting of one benzoxazole and one benzoxazine ring. The reaction works equally well with 1-phenyl-3-chloro-1-propyne. It was also found that 5-diethylamino-2-nitrosophenol reacts with R-CH2Br (R = aryl or vinyl) to give benzoxazoles with good functional group tolerance and high yield.
