Direct C伪-heteroarylation of structurally diverse ethers via a mild N-hydroxysuccinimide mediated cross-dehydrogenative coupling reaction was written by Liu, Shihui;Liu, Aoxia;Zhang, Yongqiang;Wang, Wei. And the article was included in Chemical Science in 2017.Name: Methyl isoquinoline-3-carboxylate This article mentions the following:
A new, efficient, N-hydroxysuccinimide (NHS) mediated, mild and metal-free CDC strategy for the direct C伪-heteroarylation of diverse ethers such as THF, tetrahydro-2H-pyran, 1,4,7,10-tetraoxacyclododecane, etc. has been developed. In this study NHS as a new and efficient mediator without using light has been identified, different to our previous benzaldehyde mediated photoredox C伪-heteroarylation. A distinct non-photoredox engaged hydrogen-atom-transfer (HAT) mechanism that uses a nitrogen-centered radical cation produced from NHS is initially revealed. Notably, only 5-10 equiv of ethers as coupling partners are used for allowing structurally diverse and complex ethers to engage in this process so as to create highly medicinally relevant (卤)-C伪-heteroarylated ethers 1-(1,4,7,10-tetraoxacyclododecan-2-yl)isoquinoline, 1-methyl-2-(tetrahydrofuran-2-yl)-1H-benzo[d]imidazole, 2-(tetrahydrofuran-2-yl)benzo[d]thiazole, etc. Furthermore, more structurally diverse heterocyclics such as 6-fluoro-2-methylquinoline, 6-methylisoquinoline, nicotinonitrile, etc. can serve as reactants for this process. In the experiment, the researchers used many compounds, for example, Methyl isoquinoline-3-carboxylate (cas: 27104-73-0Name: Methyl isoquinoline-3-carboxylate).
Methyl isoquinoline-3-carboxylate (cas: 27104-73-0) belongs to isoquinoline derivatives. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. The Pomeranz鈥揊ritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Name: Methyl isoquinoline-3-carboxylate
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem