863870-89-7Relevant articles and documents
Transition Metal-Free Synthesis of Halobenzo[b]furans from O-Aryl Carbamates via o-Lithiation Reactions
Feberero, Claudia,Renedo, Lorena,Sanz, Roberto,Sedano, Carlos,Suárez-Pantiga, Samuel,Virumbrales, Cintia
, (2022/01/24)
A straightforward and transition metal-free one-pot protocol to synthesize halobenzo[b]furans has been developed employing simple and easily available starting materials such as O-aryl carbamates and alkynylsulfones. The fine-tuning of the different steps involved was key to achieving a successful one-pot procedure. Initially, a directed ortho-lithiation process, which uses the carbamate as the directed metalation group, was crucial in providing access to O-2-alkynylaryl N,N-diethyl carbamates by a direct alkynylation of the o-lithiated carbamate, with arylsulfonylalkynes as electrophilic reagents. Cyclization of the generated o-alkynylaryl carbamates was successfully accomplished through a strategy involving in situ carbamate alkaline hydrolysis under conventional heating or microwave irradiation, coupled with a subsequent heterocyclization step delivering the desired benzo[b]furans. A wide variety of new halobenzo[b]furans has been synthesized and their utility has been demonstrated by their further transformation.
Method for synthesizing benzofuranol derivative by nickel-catalysis of phenethynyl phenol under microwave irradiation
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Paragraph 0025; 0039, (2018/09/11)
The invention discloses a method for synthesizing a benzofuranol derivative by nickel-catalysis of phenethynyl phenol under microwave irradiation; a catalytic amount of catalyst nickel chloride, ligand 1,10-phenanthroline(1,10-Phen), auxiliary catalyst po
A new and efficient synthesis of 4-functionalized benzo[6]furans from 2,3-dihalophenols
Sanz, Roberto,Castroviejo, M. Pilar,Fernandez, Yolanda,Fananas, Francisco J.
, p. 6548 - 6551 (2007/10/03)
Tandem Sonogashira coupling/5-endo-dig cyclization reactions on 2,3-dihalophenols suppose a straightforward entry to 4-halobenzo[b]furans, which can be easily transformed into 4-functionalized benzo[b]furans, that are difficult to synthesize by other proc
Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
Pirrung, Michael C.,Shuey, Steven W.
, p. 3890 - 3897 (2007/10/02)
Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically.These compounds can be useful in light-directed synthesis and caging.The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields.Two groups, 2',3'-dimethoxybenzoin and 3',5'-dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters.These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism.An asymmetric synthesis of 3',5'-dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols.A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives.These compounds were deprotected photochemically to produce the phosphodiesters in high yield.
