Substituent effect on local aromaticity in mono and di-substituted heterocyclic analogs of naphthalene was written by Mohajeri, Afshan;Shahamirian, Mozhgan. And the article was included in Journal of Physical Organic Chemistry in 2010.Synthetic Route of C10H9NO This article mentions the following:
A quant. study on local aromaticity has been performed on a series of mono- and di-substituted biheterocycles (quinoline, isoquinoline, quinoxaline, quinazoline). Three electronically based indexes (PDI, ATI, and FLU) have been employed to investigate the substituent effect on the π-electron delocalization in both heterocycle and benzenoid rings. Three typical substituents (Cl, OCH3, and CN) with different inductive and resonance power have been selected. Generally, substituent causes a reduction in aromaticity irresp. of whether it is electron attracting or electron donating. It is shown that the maximum aromaticity exhibits a similar trend of Cl > CN > OCH3 for all the studied rings. Moreover, it is found that the substituent situation with respect to the heteroatom has a significant influence on the aromaticity. It results from our study that in di-substituted derivatives, irresp. of whether the two substituents form a meta or para isomer, they preferably choose the position which leads to the maximum aromaticity character. Copyright © 2009 John Wiley & Sons, Ltd. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Synthetic Route of C10H9NO).
4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. The discovery of chloroquine, the most well-known drug containing this stent, has helped bring about decades of malaria control and treatment.Synthetic Route of C10H9NO
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem