Gold-Catalyzed Formal [4 + 2] Cycloaddition of 5-(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo[ g]quinolines.

doi:10.1021/acs.orglett.8b00267

Paper

Gold-Catalyzed Formal [4 + 2] Cycloaddition of 5-(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo[ g]quinolines.

Published Feb 26, 2018 · Xiaoyu Chen, J. Merrett, Philip Wai Hong Chan

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24

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0

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Abstract

A synthetic method to prepare 1,2,3,5-tetrahydrobenzo[ g]quinolines efficiently that relies on gold(I)-catalyzed cycloisomerization of 5-(ethynylamino)pent-2-yn-1-yl esters at room temperature under atmospheric conditions is described. The proposed reaction mechanism presents a unique instance of an in situ formed allenic ester and gold keteniminium species to undergo a formal [4 + 2] cycloaddition pathway.

Study Snapshot

Gold(I)-catalyzed cycloisomerization of 5-(ethynylamino)pent-2-yn-1-yl esters efficiently prepares 1,2,3,5-tetrahydrobenzo[g]quinolines under atmospheric conditions, offering a unique reaction

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Gold-Catalyzed Formal [4 + 2] Cycloaddition of 5-(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo[ g]quinolines.

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