New approach to the synthesis of non-benzenoid aromatic compounds, functionalized 1-azaazulene derivatives: Cyclization reactions of 2-substituted tropones with N-silylenamine and enamine

New approach to the synthesis of non-benzenoid aromatic compounds, functionalized 1-azaazulene derivatives: Cyclization reactions of 2-substituted tropones with N-silylenamine and enamine

Creators Sakai Norio

Creators Hattori Naoto

Creators Tomizawa Nanako

Creators Abe Noritaka

Creators Konakahara Takeo

The reaction of enamines with 2-subsituted tropones produced functionalized 1-azaazulene derivatives. When the reaction is conducted in an aprotic solvent, such as DMSO, the desired 1-azaazulene was obtained in 51% yield. The introduction of an electron-donating group on the enamine increased its nucleophilicity and improved the product yield. On the other hand, the reaction of enamines with 4-isopropyltropone-2-tosylate afforded a different 1-azaazulene derivative.

[ISSN]0385-5414

[NCID]AA00663739