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Modular Synthesis of Bicyclic and Tricyclic (Aza‐) Arenes from Nucleophilic (Aza‐)Arenes with Electrophilic Side Arms via [4+2] Annulation Reactions
Author(s) -
Huang Wenbo,
Chen Shaomin,
Yang Jian,
ElHarairy Ahmed,
Wang Xin,
Li Minghao,
Gu Yanlong
Publication year - 2019
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.201900425
Subject(s) - chemistry , bicyclic molecule , nucleophile , annulation , electrophile , trifluoromethanesulfonate , tricyclic , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
An efficient strategy for the synthesis of bicyclic and tricyclic (aza‐)arenes from a nucleophilic (aza‐)arene with an electrophilic side arm was developed. The (aza‐)arene precursor has both nucleophilic and electrophilic sites, which were fixed at a 1,4‐distance. The bicyclic and tricyclic (aza‐)arene products were constructed via [4+2] annulation by using scandium(III) triflate as a catalyst and enolizable ketones or aldehydes as the counterpart reagents. A variety of six‐membered carbocycles and heterocycles, such as indolizines, indoles, naphthalenes, carbazoles, and pyrido[1,2‐α]indoles, were successfully synthesized. Some one‐pot sequential reactions were also developed, in which the 1,4‐donor‐acceptor precursors can be synthesized via oxidation of alcohols or a proper condensation reaction.