79893-97-3Relevant articles and documents
Facile synthesis of aryl-substituted pyridines via Suzuki-Miyaura approach
Karadeniz, Eda,Zora, Metin,Kili?aslan, Nihan Zülay
, p. 8943 - 8952 (2015)
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
Zinc Chloride Mediated Synthesis of 1,4-Oxazepines from N-Propargylic β-Enaminones
Kelgokmen, Yilmaz,Cayan, Yasemin,Zora, Metin
, p. 7167 - 7178 (2017)
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 2-Acetyl-1 H-pyrroles from N-Propargylic β-Enaminones via Intermediacy of 1,4-Oxazepines
Kanova, Nilay,Dundar, Buse Aysen,Kelgokmen, Yilmaz,Zora, Metin
, p. 6289 - 6304 (2021/05/06)
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.
A new strategy for the synthesis of pyridines from: N -propargylic β-enaminothiones
Kelgokmen, Yilmaz,Zora, Metin
supporting information, p. 2529 - 2541 (2019/03/06)
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.
