Aromatic C=C bonds as dipolarophiles: Facile reactions of uncomplexed electron-deficient benzene derivatives and other aromatic rings with a non-stabilized azomethine ylide was written by Lee, Sunyoung;Diab, Sonia;Queval, Pierre;Sebban, Muriel;Chataigner, Isabelle;Piettre, Serge R.. And the article was included in Chemistry – A European Journal in 2013.Synthetic Route of C9H6N2O2 This article mentions the following:
Non-stabilized azomethine ylide 4a reacts smoothly at room temperature with a variety of uncomplexed aromatic heterocycles and carbocycles on the condition that the ring contains at least one or two electron-withdrawing substituents, resp. Aromatic substrates, including pyridine and benzene derivatives, participate as 2π components in [3+2] cycloaddition reactions and interact with one, two, or three equivalent(s) of the ylide, depending on their structure and substitution pattern. Thus, this process affords highly functionalized polycyclic structures that contain between one and three pyrrolidinyl ring(s), e.g., I, in useful yields. These results indicate that the site selectivity of the cycloaddition reactions strongly depends on both the nature and the positions of the substituents. In most cases, the second 1,3-dipolar reaction occurs on the opposite face to the one that contains the first pyrrolidinyl ring. DFT calculations on model compounds indicate that a concerted mechanism features a low activation barrier. In the experiment, the researchers used many compounds, for example, 5-Nitroisoquinoline (cas: 607-32-9Synthetic Route of C9H6N2O2).
5-Nitroisoquinoline (cas: 607-32-9) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.Synthetic Route of C9H6N2O2
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem