Aromatization issue

This:





O=C1NC2=CC=CC=C2NC1=O





aromatizes into this:





O=c3[nH]c4ccccc4[nH]c3=O

Hello,





We see a very small tranche of our database that is aromatized in this way but we agree this is unexpected without charge separation.





i.e. we might expect somthing like:





CCOc1ccc(cc1CN2C(=O)C(=O)N(Cc3ccccc3)c4ccc(Cl)cc24)C(C)=O


>>


CCOc1ccc(cc1C[N+]2=C([O-])C([O-])=[N+](Cc3ccccc3)c4ccc(Cl)cc24)C(C)=O


>>


CCOc1ccc(cc1C[n+]2c([O-])c([O-])[n+](Cc3ccccc3)c4ccc(Cl)cc24)C(C)=O





and not (currently as is):





CCOc1ccc(cc1CN2C(=O)C(=O)N(Cc3ccccc3)c4ccc(Cl)cc24)C(C)=O


>>


CCOc1ccc(cc1Cn2c3cc(Cl)ccc3n(Cc4ccccc4)c(=O)c2=O)C(C)=O





Perhaps there is an alternative approach?





Cheers,


Daniel.

Actually there are two different approach of aromatization: Basic and General.


For the comparison of the two method see:


http://www.chemaxon.com/marvin/doc/user/aromatization-doc.html





As far as I see the Basic method is more closer to your needs.





Andras