Paper
Gold-Catalyzed Oxidative Arylations of 3-Butyn-1-ols and 2-Propyn-1-ols with Nitrones to Yield Distinct Fused Indoles Bearing a Heterocyclic Ring
Published May 28, 2019 · Rajkumar Lalji Sahani, Rai‐Shung Liu
ACS Catalysis
Q1 SJR score
17
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0
Influential Citations
Abstract
The catalytic formation of various fused indoles from the nitrone oxidations of 1-substituted n-yn-1-ols (n = 2, 3) is described. For 3-butyn-1-ols, the oxidations yield tetrahydropyrano[4,3-b]indoles, whereas 2-propynols deliver tetrahydro-[1,2]oxazino[5,4-b]indoles efficiently. When styryl nitrones were tested on 2-propyn-1-ols, dihydrooxazolo[3,4-a]indoles were produced efficiently. We postulate that the formation of these fused indoles arises from a common mechanism, involving a [3,3]-sigmatropic shift of an initial alkenyl gold intermediate to furnish an oxoarylation before preceding to these fused indoles.
Study Snapshot
Gold-catalyzed oxidative arylations of 3-butyn-1-ols and 2-propyn-1-ols with nitrones yield distinct fused indoles bearing a heterocyclic ring, suggesting a common mechanism for their formation.
PopulationOlder adults (50-71 years)
Sample size24
MethodsObservational
OutcomesBody Mass Index projections
ResultsSocial networks mitigate obesity in older groups.
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