83575-92-2Relevant articles and documents
A new strategy for the synthesis of pyridines from: N -propargylic β-enaminothiones
Kelgokmen, Yilmaz,Zora, Metin
, 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.
Base-Promoted β-C(sp3)-H Functionalization of Enaminones: An Approach to Polysubstituted Pyridines
Shen, Jinhai,Cai, Dingding,Kuai, Changsheng,Liu, Yunqi,Wei, Ming'E,Cheng, Guolin,Cui, Xiuling
, p. 6584 - 6589 (2015/10/06)
A convenient one-pot base-promoted synthesis of polysubstituted pyridines from 1-arylethylamines and ynones through the direct β-C(sp3)-H functionalization of enaminones under metal-free conditions has been developed. An intermolecular Michael addition reaction and an intramolecular condensation were involved in this procedure, which features high regioselectivity, high efficiency, and environmental friendliness. Various polysubstituted pyridines were provided in up to 92% yield for 34 examples.
Cyclization reactions of 3,4-diazaheptatrienyl metal compounds. Pyridines from an anionic analogue of the Fischer indole synthesis: Experiment and theory
Kleine, Tillmann,Froehlich, Roland,Wibbeling, Birgit,Wuerthwein, Ernst-Ulrich
, p. 4591 - 4599 (2011/07/30)
Unsymmetrical N,N′-bisalkylidene hydrazines 7a,b, 10a-c and 13, which are accessible in good to excellent yields from hydrazones 6, 9, and 12 and commercially available α,β-unsaturated carbonyl compounds, are converted into 3,4-diazaheptatrienyl anions 14