736185-12-9

Upstream product

• 90003-91-1 1-iodo-2-(methoxymethyl)benzene 
• 1066-54-2 trimethylsilylacetylene 
• 5159-41-1 2-iodobenzyl alcohol 
• 40400-13-3 2-Iodobenzyl bromide 
• 38274-16-7 2-bromo-1-(trimethylsilylethynyl)benzene 
• 107-30-2 chloromethyl methyl ether 

Relevant academic research and scientific papers

ALKYNYL PHOSPHINE GOLD COMPLEXES FOR TREATING BACTERIAL INFECTIONS

A compound of formula (I) for use in the prevention or treatment of a bacterial infection.

Diisobutylaluminum hydride-promoted cyclization of benzyl and phenylsilyl ethers bearing a 2-(trimethylsilyl)ethynyl group: syntheses of indenes and benzosiloles

The reaction of o-[2-(trimethylsilyl)ethynyl]benzyl methyl ethers with diisobutylaluminum hydride (DIBAL-H) gave 2-(trimethylsilyl)indenes in good yields. This cyclization proceeds by regio- and stereoselective hydroalumination of the alkyne moiety followed by intramolecular nucleophilic substitution. o-[2-(Trimethylsilyl)ethynyl]phenylsilyl methyl ethers also underwent the DIBAL-H promoted-cyclization to be converted into 2-(trimethylsilyl)benzosiloles in good yields. This approach provides straightforward and efficient way to construct benzosiloles from readily available organosilanes.

Gold(I)-Catalyzed Intramolecular Carbon-Oxygen Bond Cleavage Reaction via Gold Carbenes Derived from Vinylidenecyclopropanes

Under gold(I) catalysis, the in situ generated gold carbene from vinylidenecyclopropanes bearing a methoxymethyl group can undergo an intramolecular nucleophilic attack to give the carbon-oxygen bond cleavage product in good yield within 15 min. and different phosphine ligands could control both Z- and E-configurations, respectively. The reaction mechanism has been clarified on the basis of deuterium- and18O-labeling experiments. This method provides a new and efficient approach to stereoselectively synthesize alkylidenecyclobutanones under mild conditions. (Figure presented.).

A concise synthesis of chiral indanes as α1A adrenoceptor partial agonists

The synthesis of a series of chiral indanes with reported α1A partial agonist activity is outlined, applying a rhodium catalysed cyclisation for template construction. This method was extended to the asymmetric synthesis of lead compound PF-037

Formation of new alkynyl(phenyl)iodonium salts and their use in the synthesis of phenylsulfonyl indenes and acetylenes http://www.mdpi.org

The preparation of phenylsulfonyl indene derivatives and phenylsulfonyl-acetylenes from readily available alkynyl(phenyl)iodonium tetrafluoroborates and triflates was investigated using phenylsulfinate as nucleophile.

Copper-catalyzed allylations of zirconocene intermediates generated from o-alkenyl or o-alkynylbenzyl ether derivatives and zirconocene-butene complex

(Chemical Equation Presented) o-Alkenyl or alkynyl benzylzirconocene intermediate, which was readily generated by the reaction of 2-alkoxymethyl-styrene or 2-alkoxymethyl-1-(trimethylsilylethynyl)-benzene derivative with zirconocene-butene complex (Negishi reagent, "Cp 2Zr"), reacted with allyl or propargyl halides in the presence of a catalytic amount of CuCl to give allylation or allenylation products. Conversion to Dane's diene, which is a key intermediate for estrone synthesis, was efficiently carried out by enyne olefin metathesis of the allylation products.

Biradicals/zwitterions from thermolysis of enyne-isocyanates. Application to the synthesis of 2(1H)-pyridones, benzofuro[3,2-c]pyridin-1(2H)-ones, 2,5-dihydro-1H-pyrido[4,3,-b]indol-1-ones, and related compounds

Thermolysis of benzannulated enyne-isocyanates 13 and enyne-isocyanates 36 and 37 promoted the cycloaromatization reactions to generate in situ O,4-didehydro-2-hydroxyquinolines and O,4-didehydro-2-hydroxypyridines, respectively, as reactive intermediates. These cycloaromatized intermediates could be captured either as biradicals and/or as zwitterions depending on the nature of the substituent at the alkynyl terminus. The intermediate derived from cycloaromatization of 13a bearing a phenyl substituent could be regarded as biradical 14, which then abstracts hydrogen atoms from γ-terpinene leading to 2(1H)-quinolinone 15. Alternatively, the same intermediate could also be regarded as zwitterion 14′, which then undergoes an initial hydride abstraction from γ-terpinene followed by protonation to produce 15. The presence of a 2-phenylethyl substituent in 13b and 37a or a 2-methylphenyl substituent in 37b also allowed the resulting intermediates to be captured intramolecularly either as biradicals or as zwitterions, producing 2(1H)-quinolinone 19, 2(1H)-pyridone 39, and benzopyranopyridine 43, respectively. On the other hand, with a 2-methoxyphenyl, a 2-(dimethylamino) phenyl, or a 3-methoxypropyl substituent, the chemical behavior of the cycloaromatized adduct could be best accounted for in terms of a zwitterionic intermediate leading to benzofuro [3,2-c]quinolin-6(5H)-one (20), 5,11-dihydro-11-methyl-6H-indolo-[3,2-c]quinolin-6-one (25), benzofuro[3,2-c]pyridin-1(2H)-one 44, 2,5-dihydro-2,5-dimethyl-1H-pyrido-[4,3-b] indol-1-one 46, and related compounds. Interestingly, thermolysis of 37f bearing a 2-(methoxymethyl)phenyl substituent at the alkynyl terminus produced the unexpected benzopyranopyridine 56 as the major product in a process involving the cleavage of the bond between the methoxyl oxygen and the adjacent methylene carbon. The efficiency and selectivity of the cycloaromatization reaction could also be enhanced by the introduction of 1.1 to 10 equiv of dimethylphenylsilyl chloride to the reaction mixture to capture the resulting zwitterion.