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Base‐Catalyzed Cyclization of 1,6‐Diynyl Carboxylates Involving Propargyl‐Allenyl Isomerization: Efficient Synthesis of Benzo[ b ]fluorene and Its Analogues
Author(s) -
Sun Ning,
Xie Xin,
Wang Gaonan,
Chen Haoyi,
Liu Yuanhong
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601074
Subject(s) - isomerization , chemistry , propargyl , fluorene , catalysis , base (topology) , thiophene , ring (chemistry) , pyridine , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry , mathematical analysis , mathematics , polymer
An efficient protocol for the synthesis of benzo[ b ]fluorenes via base‐catalyzed cyclization of 1,6‐diynyl carbonates, esters or ethers has been developed. The reaction likely proceeds via base‐induced propargyl‐allenyl isomerization followed by Schmittel‐type cyclization. Heterocycle‐fused fluorenes such as thiophene‐ or pyridine‐fused substrates could also be conveniently constructed by this method. The synthetic utility of this reaction was demonstrated by the preparation of up to seven‐ring fused polycyclic aromatic hydrocarbons.