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Chem Commun (Camb). 2018 Sep 13;54(74):10415-10418. doi: 10.1039/c8cc05018j.

Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons.

Author information

1
School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. China. wjhao@jsnu.edu.cn laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.

Abstract

The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were established for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields. The naphthannulation reaction of yne-allenone esters with β-ketonitriles provided new phenanthrene-1-carboxylates via a base-mediated [2+2] cycloaddition/ring expansion sequence, whereas hitherto unreported tetracyclic tetrahydrotetraphene-7-carboxylates were obtained with good yield via a sequential double annulation cascade of yne-allenone esters with dimedone as a diphilic reagent.

PMID:
30069562
DOI:
10.1039/c8cc05018j

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