230-31-9Relevant articles and documents
Coarctate versus pericyclic reactivity in naphthalene-fused azo-ene-ynes: Synthesis of benzocinnolines and benzoisoindazoles
McClintock, Sean P.,Zakharov, Lev N.,Herges, Rainer,Haley, Michael M.
, p. 6798 - 6806 (2011)
The cyclization reactions of naphthalene-fused azo-ene-yne compounds are explored both computationally and experimentally. Calculations reveal that naphtho-fusion to an azo- ene-yne scaffold does not significantly alter the transition state energies compared to the benzene-based systems; however, fusing the naphthalene in an angular fashion leads to lower energy intermediates due to the creation of arenes possessing greater aromaticity. Experimentally, the cyclization of the angular systems yields not only the expected monomeric benzocinnolines and benzoisoindazoles, but also several dimeric structures, including one that readily isomerizes in the presence of light and/or trace acid. Copyright
Benzocinnolin
Bluhm, Thorsten
, p. 189 - 190 (2007/10/02)
The synthesis of benzocinnolin (3) is reported.Its spectroscopic properties (uv, luminescence, pmr, ms) are similar to the other diazaphenanthrenes containing a diazine ring.The lowering of the basicity of 3 compared with a monoazaphenanthrene like other diaza-aromatic compounds appears to be due to an electrostatic field effect and not to an inductive effect.
