79893-97-3

Upstream product

• 98-88-4 benzoyl chloride 
• 536-74-3 phenylacetylene 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 2450-71-7 Propargylamine 

Downstream Products

• 1034842-17-5 C₂₅H₂₁NO 
• 1034842-21-1 C₂₇H₂₃NO₃ 
• 1034842-25-5 C₂₄H₁₈N₂O₃ 
• 1599465-95-8 (3-methylene-4,5-diphenyl-3,4-dihydro-2H-pyrrol-4-yl)(phenyl)methanone 
• 1599466-04-2 (3-methylene-4-(naphthalen-2-yl)-5-phenyl-3,4-dihydro-2H-pyrrol-4-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Facile synthesis of aryl-substituted pyridines via Suzuki-Miyaura approach

A facile and efficient synthetic route to arylpyridines is reported. When heated with boronic acids in the presence of 5 mol % PdCl2(PPh3)2 and KHCO3 in 4:1 DMF/H2O solution at 110°C, 5-iodopyridines

Cu-Catalyzed iminative hydroolefination of unactivated alkynes en route to 4-imino-tetrahydropyridines and 4-aminopyridines

A general method for synthesizing 4-imino tetrahydropyridine derivatives is achieved, from readily available β-enaminones and sulfonyl azides, which comprises a sequential copper catalyzed ketenimine formation and its hitherto inaccessible intramolecular hydrovinylation. The products are shown as ready precursors for highly valuable 4-sulfonamidopyridine derivatives via DDQ mediated oxidation.

Zinc Chloride Mediated Synthesis of 1,4-Oxazepines from N-Propargylic β-Enaminones

An efficient and general method for the synthesis of 1,4-oxazepines is described. When reacted with ZnCl2 in DCM at 40 °C or CHCl3 at 61 °C, N-propargylic β-enaminones undergo 7-exo-dig cyclization to afford 2-methylene-2,3-dihydro-1,4-oxazepines in good to high yields. This cyclization has been found to be general for a diverse range of N-propargylic β-enaminones, and proceeds with high efficiency and with broad functional group tolerance. The reactions in refluxing CHCl3 produced 1,4-oxazepines in comparatively short reaction times and with better yields that those obtained in refluxing DCM. This operationally easy method may provide rapid access to a library of functionalized 1,4-oxazepine derivatives of pharmacological interest.

One-pot synthesis of iodine-substituted 1,4-oxazepines

A facile one-pot method for the synthesis of iodine-substituted 1,4-oxazepines is reported. When reacted with ZnCl2 and I2 in DCM at 40 °C, N-propargylic β-enaminones, prepared by the conjugate addition of propargylamine to α,β-alkynic ketones, underwent 7-exo-dig cyclization by zinc chloride and concomitant reaction with molecular iodine to afford 2-(iodomethylene)-2,3-dihydro-1,4-oxazepines in good to high yields. This cyclization was found to occur with broad scope of substrates and high tolerance of functional groups. The resulting iodine-containing 1,4-oxazepines can be further elaborated to more complex structures by subsequent cross-coupling reactions, which may provide a platform for biological studies.

One-Pot Synthesis of 2-Acetyl-1 H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines

A one-pot two-step protocol for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic β-enaminones was described. When treated with zinc chloride in refluxing chloroform, N-propargylic β-enaminones produced in situ 2-methylene-2,3-dihydro-1,4-oxazepines, which, upon further refluxing in methanol with zinc chloride, afforded 2-acetyl-1H-pyrroles. The process was found to be general for a wide variety of N-propargylic β-enaminones and yielded a diverse range of 2-acetyl-1H-pyrroles in good to high yields with large substrate scope and good functional group tolerance. This operationally easy method may provide a rapid access to functionalized 2-acetyl-1H-pyrroles of pharmacological interest.

Transition-Metal-Free Synthesis of Pyridine Derivatives by Thermal Cyclization of N -Propargyl Enamines

A transition-metal-free synthesis of pyridine derivatives by 6- endo - dig cyclization of N -propargyl enamines was developed. This method is environmentally friendly and is a high atom economy reaction that is easily accessed to provide pyridine derivatives in moderate to good yield by heating N -propargyl enamines in solvent without additives. The total synthesis of onychine was achieved in 51% yield in only two steps by using this method.

A new strategy for the synthesis of pyridines from: N -propargylic β-enaminothiones

A new method for the synthesis of 2,4,5-trisubstituted pyridines from N-propargylic β-enaminothiones is reported. β-Enaminothiones were prepared by thionation of the corresponding β-enaminones with Lawesson's reagent. When treated with diisopropylamine in DMF at room temperature, N-propargylic β-enaminothiones yielded 2,4,5-trisubstituted pyridines in moderate to high yields, along with small amounts of 2-methylene-2,3-dihydro-1,4-thiazepines. The reaction was found to be general for a broad range of N-propargylic β-enaminothiones and tolerated the presence of aromatic, heteroaromatic and aliphatic groups with electron-withdrawing and electron-donating substituents. The method could be widened to the internal alkyne-tethered N-propargylic β-enaminothiones. This operationally simple method may provide rapid access to a library of functionalized pyridines of pharmacological interest.

Synthesis of novel 3-[(1-glycosyl-1H-1,2,3-triazol-4-yl)- methylamino]ket-2-en-1-ones

[Figure not available: see fulltext.] Nine 3-[(1-β-D-ribofuranosyl- and 3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones have been synthesized by copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction between propargylamine

Base-promoted ring-closing carbonyl-allene metathesis for the synthesis of 2,4-disubstituted pyrroles

A base-promoted ring-closing carbonyl-allene metathesis reaction of N-allenyl β-enaminones (generated in situ from N-propargyl β-enaminones) gives 2,4-disubstituted pyrroles with cleavage of the C(sp)-C(sp3) bond. This transition metal-free procedure generates 1 equiv. of acetic acid as the sole byproduct. A preliminary mechanistic study supports a stepwise [2 + 2] cycloaddition/retro [2 + 2] reaction pathway.

Facile synthesis of heavily-substituted alkynylpyridines via a Sonogashira approach

A facile and efficient synthetic route to densely substituted alkynylpyridines via a Sonogashira approach is reported. When treated with terminal alkynes in the presence of 5 mol% PdCl2(PPh3)2, 5 mol% CuI and excess Etsub