2-Amino-4-arylazulene derivatives were prepared from 8-aryl-2-cyclohepta[]furan-2-ones, which were converted into 6-aryl-7-naphth[3,2,1-]azulen-7-ones through a several step process. The reaction of 8-aryl-2-cyclohepta[]furan-2-ones bearing an ester group at the 3-position with malononitrile in the presence of triethylamine afforded 2-amino-4-arylazulenes. The prepared 2-amino-4-arylazulenes were converted to the corresponding 2-chloro derivatives by the Sandmeyer reaction, which were subsequently transformed into 2,4-diarylazulenes by Suzuki-Miyaura coupling with various aryl boronic acids. 2,4-Diarylazulenes underwent intramolecular cyclization between aryl and cyano groups by Brønsted acid to give 6-aryl-7-naphth[3,2,1-]azulen-7-ones. UV/vis spectral analysis revealed that 6-aryl-7-naphth[3,2,1-]azulen-7-one with a ,-dimethylaminophenyl group at the 6-position exhibited a broad and strong absorption band in the visible region due to intramolecular charge transfer. Furthermore, 6-aryl-7-naphth[3,2,1-]azulen-7-ones exhibited halochromism in 30% CFCOH/CHCl. Although fluorescence was not observed in solution, 8-aryl-2-cyclohepta[]furan-2-ones with an ester function were found to fluoresce in the solid state. 6-Aryl-7-naphth[3,2,1-]azulen-7-ones also displayed spectral changes with good reversibility under the electrochemical redox conditions.

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http://dx.doi.org/10.1021/acs.joc.4c01394DOI Listing

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2-Amino-4-arylazulene derivatives were prepared from 8-aryl-2-cyclohepta[]furan-2-ones, which were converted into 6-aryl-7-naphth[3,2,1-]azulen-7-ones through a several step process. The reaction of 8-aryl-2-cyclohepta[]furan-2-ones bearing an ester group at the 3-position with malononitrile in the presence of triethylamine afforded 2-amino-4-arylazulenes. The prepared 2-amino-4-arylazulenes were converted to the corresponding 2-chloro derivatives by the Sandmeyer reaction, which were subsequently transformed into 2,4-diarylazulenes by Suzuki-Miyaura coupling with various aryl boronic acids.

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