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 ...


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


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, ...

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