359636-50-3

Upstream product

• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 30389-18-5 1-Ethynylcyclohexylamine 

Downstream Products

• 1033037-48-7 (E)-4-(1-chloromethylidene)-2-phenyl-3-oxa-1-aza-spiro[4.5]dec-1-ene 
• 1033037-49-8 (Z)-4-(1-chloromethylidene)-2-phenyl-3-oxa-1-aza-spiro[4.5]dec-1-ene 
• 680570-94-9 4-methylene-2-phenyl-3-oxa-1-azaspiro[4.5]dec-1-ene 

Relevant academic research and scientific papers

Dual H-bond activation of NHC-Au(i)-Cl complexes with amide functionalized side-arms assisted by H-bond donor substrates or acid additives

Novel approach with amide-tethered H-bond donor NHC ligands enabled Au(i)-catalysis via H-bonding. The plain NHC-Au(i)-Cl complex catalysed conversions of terminal N-propynamides to oxazolines, and enyne cycloisomerization with an acid additive, in DCM at

Gold-Catalyzed Stereoselective Domino Cyclization/Alkynylation of N-Propargylcarboxamides with Benziodoxole Reagents for the Synthesis of Alkynyloxazolines

A concise and highly stereoselective synthesis of alkynyloxazolines via a gold-catalyzed domino cyclization-alkynylation cascade of N-propargylcarboxamides with benziodoxole reagents is reported. This new protocol, which represents an attractive alternati

Palladium-Catalyzed Cascade Difluoroalkylation/Cyclization of N-Propargylamides: Synthesis of Oxazoles and Oxazolines

A palladium-catalyzed process to construct oxazoles and oxazolines with broad functional-group tolerance has been developed, and the method introduces difluoromethyl groups into heterocycles in a one-pot fashion. This system uses a carbonyl oxygen as the acceptor for the addition of a vinylpalladium intermediate to achieve the cyclization. Oxazoline derivatives are generated as the Z-isomer with high stereoselectivity. Additionally, we validated the tentative mechanism of this reaction.

Sulfur–Fluoride Exchange (SuFEx)-Mediated Synthesis of Sterically Hindered and Electron-Deficient Secondary and Tertiary Amides via Acyl Fluoride Intermediates

Amide bond formation is one of the most executed reactions in chemistry and biology. This is largely due to the ubiquity of the amide functional group in biological molecules, natural products and pharmaceutically important drugs. We report here the development of “SuFExAmide”: a new sulfur–fluoride exchange (SuFEx) click chemistry based protocol for the efficient amidation of carboxylic acids via acyl fluoride intermediates. We have developed benzene-1,3-disulfonyl fluoride as a cost effective, powerful and versatile coupling agent, which delivers challenging secondary and tertiary amides in excellent yields from sterically hindered and electron-deficient amines. The straightforward method offers significant benefits over existing protocols in terms of substrate scope, efficiency and ease of operation and is demonstrated by the synthesis of 44 amides, including GNF6702, an antiprotozoal drug candidate. In the majority of cases, the amide products are obtained in high yield without the need for excess reagents or chromatographic purification.

Cu(I)-catalyzed synthesis of dihydropyrimidin-4-ones toward the preparation of β- And β3-amino acid analogues

A copper(I)-catalyzed synthesis of substituted dihydropyrimidin-4-ones from propargyl amides via the formation of ketenimine intermediate has been successfully developed; the synthesis afforded good isolated yields (80-95%). The mild reaction conditions at room temperature allow the reaction to proceed to completion in a few hours without altering the stereochemistry. Further, by involving a variety of reactive nucleophiles, the obtained substituted dihydropyrimidin-4-ones were elegantly transformed into the corresponding β- and β3-amino acid analogues.

Cyclobutene formation in PtCl2-catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes

Aza(oxa)bicyclo[3.2.0]heptenes are accessed through the PtCl 2-catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes featuring a terminal alkyne and amide as the solvent. It is shown that the weak coordinating properties of the solven

CuI-catalyzed cycloisomerization of propargyl amides

The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidized to the ketone under the reaction conditions.

Facile, selective, and regiocontrolled synthesis of oxazolines and oxazoles mediated by ZnI2 and FeCl3

An expedient method for a direct approach to the selective and regiocontrolled synthesis of 2-oxazolines and 2-oxazoles mediated by ZnI 2 and FeCl3 is described. A Lewis acid promoted cyclization of acetylenic amide with various func

Cyclization-carbonylation-cyclization coupling reactions of propargyl acetates and amides with palladium(II)-bisoxazoline catalysts

Clever boxing: A cyclization-carbonylation-cyclization-coupling reaction of propargyl acetates 1 or amides 2 in the presence of a palladium(II)- bisoxazoline (box) catalyst afforded symmetrical ketones of types 3 and 4, respectively, containing two heterocyclic groups in moderate to excellent yields (see scheme; tfa=trifluoroacetate). Compounds 3 were converted into ketones containing two 3(2H)-furanone rings.

Intramolecular Pd(II)-catalyzed cyclization of propargylamides: Straightforward synthesis of 5-oxazolecarbaldehydes

(Chemical Equation Presented) Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reox