94411-73-1Relevant academic research and scientific papers
Rh-Catalyzed C-H Amination/Annulation of Acrylic Acids and Anthranils by Using -COOH as a Deciduous Directing Group: An Access to Diverse Quinolines
Gao, Yang,Nie, Jianhong,Li, Yibiao,Li, Xianwei,Chen, Qian,Huo, Yanping,Hu, Xiao-Qiang
supporting information, p. 2600 - 2605 (2020/04/02)
A method for the synthesis of diverse polysubstituted quinolines from readily available acrylic acids and anthranils has been developed. The weakly coordinating -COOH directing group, which can be tracelessly removed in the cascade cyclization, is essential for this reaction. Diverse polysubstituted quinolines were obtained under mild reaction conditions with simple H2O and CO2 as byproducts. More importantly, 1,2,3,4-tetrahydroacridine, which is the core skeleton of tacrine (an Alzheimer's disease drug), was conveniently synthesized.
Pyrans, 100. - 5,6-Dihydro-2H-pyran-3(4H)-one as a Building Unit for the Synthesis of Pyran-annulated Heterocyclic Compounds
Eiden, Fritz,Wanner, Klaus Th.
, p. 1759 - 1777 (2007/10/02)
Only in a few cases 5,6-dihydro-2H-pyran-3(4H)-one (3) reacts regioselectively with ortho-substituted phenylcarbonyl compounds to form pyran-annulated heterocyclic compounds like the pyranoquinoline 7c.Better results are obtained in reactions involving the enamine 15d derived from 3, the silyl enol ether 18 and the lithium enolate 14 derived from 18.These pyran derivatives with 2,3- or 3,4-double bonds are well suited for successful synthesis of 2-or 4-substituted 3-pyranones such as 2, 21a, 21b, 23a - c, 26a - c, 31a - c, 32, and 35a - c.They also allow to synthesize pyrano- or -quinolines, -quinolones, -chromones, and -thiochromones 6a, 30a - c, 38a - d.
