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Didehydroisobenzofuran: A New Reactive Intermediate for Construction of Isoacenofuran
Author(s) -
Matsuoka Suguru,
Jung Sunna,
Miyakawa Kaoru,
Chuda Yu,
Sugimoto Ryo,
Hamura Toshiyuki
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804655
Subject(s) - bromine , reactive intermediate , lithium (medication) , chemistry , class (philosophy) , combinatorial chemistry , organic chemistry , computer science , biology , catalysis , artificial intelligence , endocrinology
An efficient generation method of didehydroisobenzofuran, a new heteroaryne species, was developed by bromine/lithium exchange of the dibromoisobenzofuran. The reactive intermediate, thus generated, was trapped by appropriate arynophile to give the [2+2], [2+3], and [2+4] cycloadducts, respectively. Moreover, the reaction could be applied to the syntheses of isoanthracenofurans (anthra[2,3‐ c ]furans), a new class of heteroacenes, with isoelectoronic structure to the corresponding acenoheteroles (anthra[2,3‐ b ]furans).