Diethyl N , N′ -dimethylpyrrol[3,4- f ]isoindole-1,7-dicarboxylate as a 14π-electronic aromatic compound with two azomethine-ylide moieties
作者:Shogo Hiraoka、Hiroyuki Tahara、Shigeki Mori、Tetsuo Okujima、Masayoshi Takase、Takahiro Nakae、Hidemitsu Uno
DOI:10.1016/j.tet.2017.01.015
日期:2017.2
8-dihydro-4,8-methanopyrrol[3,4-f]isoindole-1,7-dicarboxylate produced diethyl 9-oxo-2,6-dimethyl-4,8-dihydro-4,8-methanopyrrol[3,4-f]isoindole-1,7-dicarboxylate. This carbonyl derivative spontaneously underwent cheletropic extrusion of carbon monoxide, producing diethyl 2,6-dimethylpyrrol[3,4-f]isoindole-1,7-dicarboxylate, which showed 14π-electronic aromaticity on the whole five-six-five ring system.
9-羟基-2,6-二甲基-4,8-二氢-4,8-甲基吡咯[3,4- f ]异吲哚-1,7-二羧酸二乙酯的Parikh-Doering氧化生成二乙基9-oxo-2,6 -二甲基-4,8-二氢-4,8-甲基吡咯[3,4- f ]异吲哚-1,7-二羧酸酯。该羰基衍生物自发地经历一氧化碳的偏压挤出,生成2,6-二甲基吡咯[3,4- f ]异吲哚-1,7-二羧酸二乙酯,在整个五六十五环体系上显示14π电子芳香性。