37881-09-7Relevant articles and documents
Access to Cycloalkeno[ c]-Fused Pyridines via Pd-Catalyzed C(sp2)-H Activation and Cyclization of N-Acetyl Hydrazones of Acylcycloalkenes with Vinyl Azides
Nie, Biao,Wu, Wanqing,Ren, Qingyun,Wang, Zhongqing,Zhang, Ji,Zhang, Yingjun,Jiang, Huanfeng
supporting information, p. 7786 - 7790 (2020/11/02)
A novel Pd(II)-catalyzed vinylic C-H activation and cyclization has been developed, reacting a series of small, medium, and large N-acetyl hydrazones of acylcycloalkenes with vinyl azides to access diverse cycloalkeno[c]-fused pyridine scaffolds. This protocol provides progress in C(sp2)-H bond activation of medium to large cycloalkenes, and the target products can be obtained in a specific regioselectivity with good functional group tolerance and a broad substrate scope.
Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); A new 'metal free' life for the Rupe rearrangement
Nandi, Ganesh C.,Rathman, Benjamin M.,Laali, Kenneth K.
supporting information, p. 6258 - 6263 (2013/10/22)
A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Br?nsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF 6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov sequence utilizing this protocol has also been demonstrated.
A Novel Synthesis of Methylenecyclopropane Spiro-Linked with Cycloalkanes via a Cyclization of Allylic Epoxides and Its Application to a Synthesis of Fused 3-Methylfurans
Satoh, Tsuyoshi,Kawase, Yasushi,Yamakawa, Koji
, p. 1129 - 1135 (2007/10/02)
Ring closure of allylic epoxides derived from 1-chloroalkyl phenyl sulfoxides and cyclic ketones with lithium diisopropylamide (LDA) in 3-Exo-Tet mode gave spiro-linked methylenecyclopropanes having a hydroxyl group in good yields.Oxidation of these compounds gave ketones, which were then treated with p-toluenesulfonic acid in 1,4-dioxane or DMSO at 100 deg C to give fused 3-methylfurans in good overall yields.This procedure was applied to a synthesis of menthofuran from 4-methylcyclohexanone.