- Iron(III) Chloride Mediated para-Selective C-H Functionalization: Access to C5-Chloro and C5,C7-Dichloro/Dianisyl Substituted 2-Arylbenzoxazoles
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Iron(III) chloride mediated para-selective C?H chlorination and subsequent annulation of 2-amidophenol to synthesize C5- and C5, C7-chlorinated benzoxazoles was developed. Further, the oxidative cross-dehydrogenative coupling of amidophenol with anisole b
- Sahoo, Kanchanbala,Panda, Niranjan
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p. 1023 - 1030
(2022/02/03)
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- Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes
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A novel and efficient methodology for the arylation of benzoxazoles with aromatic aldehydes catalyzed by deep eutectic solvent has been developed. The reaction smoothly proceeded with a wide range of substrates to give the desired products in high yields within short reaction time. Deep eutectic solvents are easily recovered and reused without significant loss of catalytic activity.
- Tran, Phuong Hoang,Thi Hang, Anh-Hung
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p. 11127 - 11133
(2018/03/26)
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- Use of Hypervalent Iodine in the Synthesis of Isomeric Dihydrooxazoles
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[Figure not available: see fulltext.] A convenient synthesis of 2- and/or 3-oxazolines has been developed depending on the structure and stereochemistry of the starting amino alcohol. PhI(OAc)2 acted as oxidant on the intermediate imine, as sup
- Carlucci, Claudia,Tota, Arianna,Colella, Marco,Ronamazzi, Giuseppe,Clarkson, Guy J.,Luisi, Renzo,Degennaro, Leonardo
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p. 428 - 436
(2018/06/11)
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- p-Toluenesulfonic acid-catalyzed metal-free formal [4?+?1] heteroannulation via N[sbnd]H/O[sbnd]H/S[sbnd]H functionalization: One-pot access to 2-aryl/hetaryl/alkyl benzazole derivatives
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A concise and direct one-pot [4?+?1] synthetic strategy for the construction of 2-substituted benzazoles such as benzoxazoles and benzothiazoles has been disclosed in high yields (80–98%) by cascade coupling reaction of 2-amino(thio)phenols with β-oxodithioesters. The current approach enables N[sbnd]H/O[sbnd]H/S[sbnd]H functionalization in one-pot under solventless condition leading to diverse benzazoles without use of any external metal. A wide range of 2-amino(thio)phenols and β-oxodithioesters are compatible toward this transformation with excellent functional group tolerance. Furthermore, we preempt the wider implications of this novel strategy by demonstrating its compatibility toward versatile diversification of DNA Topoisomerase-II inhibitors.
- Srivastava, Abhijeet,Shukla, Gaurav,Singh, Maya Shankar
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p. 879 - 887
(2017/01/25)
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- KMnO4/HOAc system promoted one-pot synthesis of benzoxazoles from o-aminophenols or oxidative cyclization of o-hydroxyarylidene anilines at room temperature
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1,3-Benzoxazoles via oxidative cyclization of corresponding o-hydroxyarylidene anilines was synthesized in the presence of KMnO4/HOAc system. This system also was applied for the one-pot synthesis of 1,3-benzoxazoles from o-amino phenols and aldehydes. The both protocols were processed at room temperature under solvent-free conditions with good to excellent yields.
- Mirjalili,Bamoniri,Bagheri
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p. 809 - 814
(2016/04/05)
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- Synthesis of 2-substituted pyrimidines and benzoxazoles via a visible-light-driven organocatalytic aerobic oxidation: Enhancement of the reaction rate and selectivity by a base
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An efficient visible-light-driven photocatalytic oxidation of various 2-substituted dihydropyrimidines and phenolic imines has been achieved using an organic photocatalyst eosin Y bis(tetrabutyl ammonium salt) (TBA-eosin Y) and inexpensive oxidant molecular oxygen. With the aid of a base, significantly enhanced photoinduced electron transfer from substrates dihydropyrimidines or phenolic imines to the excited state of TBA-eosin Y has enabled the aerobic oxidation to yield 2-(methylthio)pyrimidines or 2-arylbenzoxazoles selectively. This journal is the Partner Organisations 2014.
- Wang, Lin,Ma, Zhi-Gang,Wei, Xiao-Jing,Meng, Qing-Yuan,Yang, Deng-Tao,Du, Shao-Fu,Chen, Zi-Fei,Wu, Li-Zhu,Liu, Qiang
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supporting information
p. 3752 - 3757
(2014/08/05)
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- Palladium-catalyzed direct arylations, alkenylations, and benzylations through C-H bond cleavages with sulfamates or phosphates as electrophiles
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(Figure Presented) catalytic system comprised of Pd(OAc)2 and bldentate ligand dppe enabled first direct arylatlons with moisture-stable aryl sulfamates as electrophlles, and proved applicable to unprecedented C-H bond functlonallzations with e
- Ackermann, Lutz,Barfuesser, Sebastian,Pospech, Jola
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supporting information; experimental part
p. 724 - 726
(2010/04/02)
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- Synthesis of benzoxazoles catalyzed by MCM-41, a green and reusable catalyst
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Benzoxazoles can be rapidly and efficiently synthesized from acyl chloride with 2-aminophenols in one simple step, which provided a practical and efficient method for high-throughput synthesis of this important class of heterocyclic compounds. Copyright Taylor & Francis Group, LLC.
- Shoar, Rahim Hekmat,Heidary, Maryam,Farzaneh, Maryam,Malakouti, Reihaneh
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scheme or table
p. 1742 - 1751
(2009/10/06)
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- Heteropolyacid as a new, green and recyclable catalyst for the synthesis of 2-aryl benzoxazole under solvent-free conditions
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A simple, convenient and general method has been developed for the synthesis of 2-arylbenzoxazole via condensation of o-aminophenols and benzoyl chloride derivatives under solvent-free conditions in the presence of a catalytic amount of heteropolyacids in good yields.
- Heravi, Majid M.,Javanmardi, Najme,Oskooie, Hossein A.,Baghernejad, Bita,Heidari, Maryam,Bamoharram, Fatemeh F.
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experimental part
p. 589 - 593
(2010/06/13)
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- A one-pot, two-step microwave-assisted synthesis of highly functionalized benzoxazoles using solid-supported reagents (SSRs)
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A one-pot, two-step protocol for the microwave-assisted solid-phase synthesis of substituted benzoxazoles has been developed starting from different polymer-bound esters we previously designed as solid-supported reagents (SSRs) for the acylation of amines, alcohols and phenols. The combination of a parallel synthesizer and a microwave reactor allowed to quickly prepare a collection of substituted benzoxaxoles in high purity and satisfactory yields. This protocol is amenable for automation and could be used for the preparation of combinatorial libraries in drug discovery programs.
- Radi, Marco,Saletti, Sara,Botta, Maurizio
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p. 4464 - 4466
(2008/09/21)
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- Hypervalent iodine(III) mediated synthesis of 2-substituted benzoxazoles
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2-Substituted benzoxazoles (6a-j, 7a-e, 7j-l) have been synthesized via the oxidative intramolecular cyclization of Schiff's bases (4a-j, 5a-e, 5j-l) using iodobenzene diacetate (IBD) as an oxidant in dry methanol. A one-pot procedure for the synthesis of 6a-j, 7a-e and 7j-l starting from o-aminophenol/p-chloro-o- aminophenol and aldehydes has also been developed.
- Prakash, Om,Batra, Anita,Sharma, Vijay,Saini, Rajesh K.,Verma, Rajender S.
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p. 1031 - 1034
(2007/10/03)
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- Hypervalent iodine in synthesis 69: An efficient synthesis of 2-arylbenzoxazoles via the palladium-catalysed carbonylation and condensation of diaryliodonium salts and o-aminophenols
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An efficient synthetic method is reported in which 2-arylbenzoxazoles have been prepared in good to excellent yields under mild reaction conditions by the palladium-catalysed carbonylation of diaryliodonium salts with o-aminophenols followed by dehydrative cyclisation.
- Zhou,Chen
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p. 235 - 237
(2007/10/03)
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