371256-80-3

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 536-74-3 phenylacetylene 
• 79-22-1 methyl chloroformate 
• 67-64-1 acetone 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 108-86-1 bromobenzene 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 

Downstream Products

• 1094602-83-1 1,1-bis(methoxycarbonyl)-2-(5'-methyl-3'-phenyl-1',3',4'-hexatrien-2'-yl)cyclopropane 
• 1225232-77-8 3-(ethoxycarbonyl)-2-methyl-5-(5-methyl-3-phenyl-1,3,4-hexatrien-2-yl)-4,5-dihydrofuran 
• 1314111-30-2 5-methyl-2,3-diphenylhexa-1,3,4-triene 
• 1463-04-3 (3-methylbut-3-en-1-ynyl)benzene 

Relevant academic research and scientific papers

Palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides

A palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides is reported. Remarkably, the orderly insertion of isocyanides affords two types of valuable N-heterocyclic products (Z)-6-imino-4,6-dihydro-1H-furo[3,4-b]pyrrol-2-amines and (E)-5-iminopyrrolones in high yields. Systematic analysis of the reaction conditions indicates that the selectivity of these N-heterocyclic products can be controlled by ligands and temperature.

Umpolung coupling of pyridine-2-carboxaldehydes and propargylic carbonatesviaN-heterocyclic carbene/palladium synergetic catalysis

The umpolung cross-coupling reaction of pyridine-2-carboxaldehydes and propargylic carbonates has been developed for the first time through N-heterocyclic carbene/palladium cooperative catalysis with the judicious selection of the palladium catalyst, ligand and N-heterocyclic carbene, giving the propargylic ketones regioselectively.

Palladium-catalyzed coupling of propargylic carbonates with N-tosylhydrazones: Highly selective synthesis of substituted propargylic N-sulfonylhydrazones and vinylallenes

An efficient palladium-catalyzed coupling of propargylic carbonates (1) with N-tosylhydrazones (2, 2′) has been carried out. A wide range of propargylic N-sulfonylhydrazones (3) and multisubstituted vinylallenes (4) can be obtained selectively by using either [PdCl2(CH3CN) 2] or [Pd2(dba)3] as catalysts. (dba=trans,trans-dibenzylideneacetone, dppp=propane-l,3- diylbis(diphenylphosphane), Ts=4-toluenesulfonyl.) Copyright

Benzo[e]isoindole-1,3-diones as potential inhibitors of glycogen synthase kinase-3 (GSK-3). Synthesis, kinase inhibitory activity, zebrafish phenotype, and modeling of binding mode

Benzo[e]isoindole-1,3-dione derivatives were synthesized, and the effects on GSK-3β activity and zebrafish embryo growth were evaluated.Aseries of derivatives show obvious inhibitory activity against GSK-3β. The most potent inhibitor, 7,8-dimethoxy-5-methylbenzo[e]isoindole-1,3-dione (8a), shows nanomolar IC50 and obvious phenotype on zebrafish embryo growth associated with the inhibition of GSK-3β at low micromolar concentration. The interaction mode between 8a and GSK-3β was characterized by computational modeling. 2009 American Chemical Society.

Copper(I)-catalyzed substitution of propargylic carbonates with diboron: Selective synthesis of multisubstituted allenylboronates

A versatile synthetic method for the preparation of the allenylboronates, Cu(I)-catalyzed reaction of propargylic carbonates with a diboron, is described. A Cu(O-t-Bu)-Xantphos catalyst system was effective for the preparation of various allenylboron comp

Efficient synthesis of maleimides and carbazoles via Zn(OTf) 2-catalyzed tandem annulations of Lsonitriles and allenic esters

Lewis acid Zn(OTf)2-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

Palladium-catalyzed synthesis of 2,3-dihydro-2-ylidene-1,4-benzodioxins

Palladium-catalyzed condensation of benzene-1,2-diol with various propargylic carbonates, afforded regio- and stereoselectively 2,3-dihydro-2-ylidene-1,4-benzodioxins. The reaction is suggested to proceed by the formation of a (σ-allenyl)palladium complex, followed by the intermolecular attack of the phenoxide ion on this complex to generate a new (σ-allyl)palladium complex in equilibrium with the corresponding (η3-allyl)palladium complex. Intramolecular attack of the phenoxide ion afforded the corresponding benzodioxan compound. This last attack occurs predominantly at the more electrophilic end of the (η3-allyl)palladium intermediate. The Z- or E-stereochemistry of the products was established by 1H NMR and proton NOE measurements and also by X-ray analysis on an example. The Z-stereochemistry generally observed is in agreement with the formation of this (η3-allyl)palladium intermediate. However, in the case of tertiary propargylic carbonates, the E-stereochemistry generally observed could be explained by an intramolecular attack of the phenoxide ion on the intermediate (σ-allyl)palladium complex, in slow equilibrium with the (η3allyl)palladium complex.