79893-98-4Relevant academic research and scientific papers
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)
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.
Base-promoted ring-closing carbonyl-allene metathesis for the synthesis of 2,4-disubstituted pyrroles
Cheng, Guolin,Lv, Weiwei,Xue, Lulu
supporting information, p. 4414 - 4417 (2018/10/17)
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.
