No. The 6 membered ring is also a part of its aromaticity.
This can be better understood by considering the Zwitterion of Caffeine.
The entire molecule is planar, conjugated and has 10π electrons(4n+2)
Reference:Slides by Nevina Keskineva
To check Aromaticity of a compound 4 criterias are to be checked
Planarity : (Sp^2) Hybridised
Conjugation: Compound should be fully conjugated
Hückel's Rule : There should be (4n+2)π electrons
So the above compound is planar, conjugated , cyclic and follows Huckel's Rule as One lone pair of O and one of N add upto 10π electrons which can be done ...
According to Huckel's rule Four Criteria for Aromaticity
The molecule needs to be (1) planar, (2) cyclic, (3) fully conjugated, and has (4) 4n+2 electrons.
Your molecule does not seem to be planar (b/c of N and O atoms) but assuming that it has a nearly planar conformation it satisfies all other criteria.
You only need to count one of Oxygen's lone pair and ...
Here is a proposed route starting from aniline.
First protect the -NH2 with t-BOC
Directed lithiation of t-BOC-aniline (sBuLi/Et2O, -75C) and quench with MeSSMe to install -SMe in the 2 position.
Directed lithiation under the same conditions quenching with Ethyl Chloroformate to install -CO2Et in the 6 position.
Oxidise the -SMe group to sulfoxide (MCPBA, ...
In the benzyne mechanism, mesomeric effects are not involved as when protons are removed, the electrons are situated in orbitals perpendicular to the pi-system, in non-bonding orbitals (which makes sense since the electrons come from a sigma bond). Therefore the electrons left over are not delocalised, which is why such a strong base is required. This also ...