37009-57-7

Upstream product

• 37009-54-4 N-(2-oxo-2-(p-tolyl)ethyl)benzamide 
• 100-47-0 benzonitrile 
• 17263-64-8 2-diazo-1-(4-methylphenyl)ethanone 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 10026-13-8 phosphorus pentachloride 
• 98-88-4 benzoyl chloride 
• 20662-88-8 2-phenyloxazole 
• 624-31-7 4-tolyl iodide 
• 62968-73-4 2-nitro-1-(p-tolyl)ethan-1-one 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 2996-92-1 phenyl trimethylsiloxane 
• 143659-19-2 5-(4-methylphenyl)-1,3-oxazole 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 100-46-9 benzylamine 

Downstream Products

• 2681-23-4 4-(2-phenyl-oxazol-5-yl)-benzaldehyde 
• 4829-87-2 triphenyl-[4-(2-phenyl-oxazol-5-yl)-benzyl]-phosphonium; bromide 

Relevant academic research and scientific papers

Access to (Z)-β-Substituted Enamides from N1-H-1,2,3-Triazoles

A direct ring-opening/nucleophilic substitution reaction of N1-H-1,2,3-triazoles has been described. Divergent (Z)-β-halogen- or sulfonyl-substituted enamides could be stereospecifically synthesized in a tunable manner. This strategy might not only enable

CO2/Photoredox-Cocatalyzed Tandem Oxidative Cyclization of α-Bromo Ketones and Amines to Construct Substituted Oxazoles

CO2/photoredox-cocatalyzed tandem oxidative cyclization of α-bromo ketones and amines for the preparation of substituted oxazoles has been achieved. The avoidance of using both transition-metal catalysts and peroxides makes this method more sustainable and renewable.

Divergent Conversion of N-Acyl-isoxazol-5(2 H)-ones to Oxazoles and 1,3-Oxazin-6-ones Using Photoredox Catalysis

The fragmentation of N-acyl-isoxazol-5-ones using visible light photoredox catalysis has been disclosed. The catalyst-controlled divergent mechanisms, namely the oxidative and reductive quenching catalytic cycle, are utilized. Various oxazoles and 1,3-oxazin-6-ones are selectively obtained from the same isoxazol-5-one skeleton under mild conditions.

Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an i 2 /Cu(NO 3) 2 ?3H 2 O-Assisted Domino Sequence

A new strategy has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available arylacetylenes and α-amino acids in the presence of Cu(NO 3) 2 ?3H 2 O and iodine. This reaction process involves the I 2 /Cu(NO 3) 2 ?3H 2 O-assisted transformation of arylacetylene to α-iodo acetophenone, Kornblum oxidation to phenylglyoxal, condensation to imine, decarboxylation/annulation/oxidation reaction sequence to approach 2,5-disubstituted oxazoles.

Metal-free iodine(iii)-promoted synthesis of 2,5-diaryloxazoles

A nonmetal-catalyzed oxidative cyclization to achieve 2,5-disubstituted oxazoles from inexpensive and readily available substituted chalcone, (diacetoxyiodo)benzene (PIDA) and ammonium acetate (NH4OAc) at room temperature is described. The reaction forms a variety of 2,5-diaryloxazoles in good to excellent yields with broad substrate scope under mild conditions without the requirement of ligands and additional bases.

Synthesis of 2,5-disubstituted oxazoles: Via cobalt(III)-catalyzed cross-coupling of N -pivaloyloxyamides and alkynes

An efficient synthesis of 2,5-disubstituted oxazoles via Co(iii) catalysis is described herein. The synthesis is achieved under mild conditions through [3+2] cycloaddition of N-pivaloyloxyamides and alkynes. The reaction operates through an internal oxidation pathway and features a very broad substrate scope. The one-step synthesis of natural products such as texamine and balsoxin has been demonstrated via this protocol.

Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis

A simple and practical method for the synthesis of substituted oxazoles has been developed using readily available α-bromoketones and benzylamines by visible-light photocatalysis at room temperature. The process, which requires 1 mol % of [Ru(bpy)3]Cl2 photocatalyst with K3PO4 and CCl3Br, is effective for accessing a variety of valuable oxazole compounds. The synthetic utility of our protocol was also demonstrated by preparing a natural product, texaline.

Direct C-H bond arylation of (benzo)oxazoles with aryl chlorides catalyzed by N-heterocyclic carbene-palladium(II)-1-methylimidazole complex

The direct C-H bond arylation of (benzo)oxazoles with aryl chlorides was achieved catalyzed by a well-defined NHC-Pd(II)-Im complex. Under the optimal conditions, various aryl chlorides were successfully applied as the arylating reagents to achieve the 2-aryl (benzo)oxazoles in acceptable to high yields, providing a convenient and alternative method for the direct C-H bond arylation of (benzo)oxazoles and enriching the chemistry of the NHC-Pd(II) complex in organic synthesis.

Reaction of alkynes and azides: Not triazoles through copper-acetylides but oxazoles through copper-nitrene intermediates

Well-defined copper(I) complexes of composition [Tpm* ,BrCu(NCMe)]BF4 (Tpm*,Br=tris(3,5- dimethyl-4-bromo-pyrazolyl)methane) or [Tpa* Cu]PF6 (Tpa=tris(3,5-dimethyl-pyrazolylmethyl)amine) catalyze the formation of 2,5-disubstituted oxazoles from carbonyl azides and terminal alkynes in a direct manner. This process represents a novel procedure for the synthesis of this valuable heterocycle from readily available starting materials, leading exclusively to the 2,5-isomer, attesting to a completely regioselective transformation. Experimental evidence and computational studies have allowed the proposal of a reaction mechanism based on the initial formation of a copper-acyl nitrene species, in contrast to the well-known mechanism for the copper-catalyzed alkyne and azide cycloaddition reactions (CuAAC) that is triggered by the formation of a copper-acetylide complex.

Copper-catalyzed oxidative cyclization of chalcone and benzylic amine leading to 2,5-diaryl oxazoles via carbon-carbon double bond cleavage

A copper-catalyzed oxidative cyclization of chalcone with benzylic amine is achieved, providing 2,5-diaryl oxazoles in moderate to good yields. The procedure employs O2 as a clean oxidant and involves an oxidative cleavage of the CC bond as the key step.