152874-20-9

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• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 
• 1066-54-2 trimethylsilylacetylene 

Relevant academic research and scientific papers

Palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination: Access to functionalized naphthalenes

A palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination of enyne-tethered allylic alcohols with aminals is described. Under the reaction conditions, the cationic vinyl allylpalladium species undergoes selective migratory insertion of alkenes rather than reductive elimination with nucleophiles. This strategy provides an efficient and unique approach to the construction of functionalized naphthalenes, which are important building blocks in synthetic organic chemistry. Mechanistic studies have revealed that the selective sequential migratory insertion of enyne and alkene is crucial for the cyclization.

Exploiting Hydrazones to Improve the Efficiency of 6π-Electrocyclization Reactions of 1-Azatrienes

The greater geometric lability of hydrazones compared to that of oxime ethers is used as a basis to overcome the reluctance of Z-oxime ether azatrienes to undergo electrocyclization toward the synthesis of borylated (heteroaromatic) pyridines and ring-fused analogues. Such hydrazones now allow access to previously inaccessible tri- and tetrasubstituted 3-borylpyridines in high yields.

Opioid receptor agonists and application thereof

The invention discloses compounds and salts thereof that can be used as opioid receptor ligands, a preparation method of the compounds, compositions containing the compounds, and a use of the compounds as [mu] opioid receptor agonists; the compounds are used for treatment of [mu] opioid receptor-mediated related diseases, such as pains and pain-related disorders.

Synthetic and Mechanistic Investigation of an Oxime Ether Electrocyclization Approach to Heteroaromatic Boronic Acid Derivatives

A range of functionalized heteroaromatic boronic acid derivatives are readily accessed by a diboration/6π-electrocyclization sequence. This study revealed the surprising observation that there is a direct relationship between oxime ether stereochemistry and reactivity towards electrocyclization. Specifically, E-oxime ethers are found to be significantly more reactive than their Z-counterparts (stereochemistry relative to azatriene scaffold). In contrast, the configuration at the azatriene alkene terminus has little impact on reaction rates. Computational analysis offers a rationale for this observation; a Nlone pair→C=C π* orbital interaction lowers the energy of the transition state in the electrocyclization of E-oxime ethers. Finally, unreactive Z-oxime ethers can be converted to the corresponding heterocyclic products by a photolytically promoted E→Z isomerization and electrocyclization sequence.

Synthesis of Fluorescent Azafluorenones and Derivatives via a Ruthenium-Catalyzed [2 + 2 + 2] Cycloaddition

An original and mild synthetic route for the preparation of novel azafluorenones and derivatives via a ruthenium-mediated [2 + 2 + 2] cycloaddition of α,ω-diynes and cyanamides has been developed. This atom-economical catalytic process demonstrated remarkable regioselectivities to access fluorescent azafluorenone derivatives. The photophysical properties of azafluorenone derivatives have been evaluated, and photoluminescence phenomena at solid and liquid states have been highlighted.

De Novo Synthesis of Phenols and Naphthols through Oxidative Cycloaromatization of Dienynes

In this work, a rhodium-catalyzed oxidative cycloaromatization of dienynes, which provides a highly straightforward and efficient way to access polysubstituted naphthols and phenols under mild conditions, is described. Challenged electron-withdrawing groups are well tolerated in this protocol, and late-stage phenyl ring formation is demonstrated.

Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones

New rhodium(II)-catalyzed or thermally induced intramolecular alkoxy group migration of N-sulfonyl-1,2,3-triazoles has been developed, affording divergent synthesis of 1,2-dihydroisoquinoline and 1-indanone derivatives according to different conditions. N-Sulfonyl keteneimine is the key intermediate for the synthesis of dihydroisoquinoline, whereas the aza-vinyl carbene intermediate results in the formation of 1-indanone.

Gold superacid-catalyzed preparation of benzo[c]thiophenes

A three-step synthesis of benzo[c]thiophenes is presented in which the key transformation is the gold-catalyzed 5-exo-dig migratory cycloisomerization of a diallyl thioacetal. It was shown that a small amount of in situ generated HAuCl4 from AuCl3 is the active catalytic species. A mechanism was proposed.

Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.

One-pot synthesis of aromatic fused 2,3-dihydroindanone by tandem Pauson-Khand/Michael/Henry reaction

The intermolecular Pauson-Khand reaction between 2-ethynylbenzaldehyde and ethylene promoted by dimethyl sulfide can be utilized to synthesize 2-(2-formylphenyl)cyclopentenone efficiently. This compound and its derivatives undergo a cascade process of Michael addition reaction followed by Henry reaction with nitromethane to construct substituted aromatic fused 2,3-dihydroindanones. Furthermore, direct one-pot synthesis of aromatic fused 2,3-dihydroindanones from 2-ethynylbenzaldehyde is achieved. Copyright