| Full text | |
| Author(s): |
Fumagalli, Fernando
;
Emery, Flavio da Silva
Total Authors: 2
|
| Document type: | Journal article |
| Source: | Journal of Organic Chemistry; v. 81, n. 21, p. 10339-10347, NOV 4 2016. |
| Web of Science Citations: | 10 |
| Abstract | |
A concise strategy for the synthesis of 2,3 substituted furo{[}2,3-b]pyridines is described. Mild, metal-free conditions were successfully applied to produce a range of 2 (alkyl or aryl)-3-ethylcarboxylate-furo{[}2,3-b]pyriclies in yields of 50-91%. Then, the chemical reactivity of this heterocyclic framework was explored to develop straightforward methods for its functionalization. The pyridine moiety reactivity was successfully explored by C-H amination and borylation reactions, although C-H fluorination and radical C-H arylation processes were not as efficient. In addition, while the furopyridine core proved stable under basic conditions, the ring-opening reaction of the furan moiety with hydrazine generated a valuable new pyridine-dihydropyrazolone scaffold. (AU) | |
| FAPESP's process: | 15/06588-5 - Development of library of heterocyclic fragments based on new heteroaromatic cores |
| Grantee: | Fernando Fumagalli |
| Support Opportunities: | Scholarships in Brazil - Doctorate |
| FAPESP's process: | 14/50265-3 - Distribution and metabolism of natural and synthetic xenobiotics: from the comprehension of reactional process to tissue imaging generation |
| Grantee: | Norberto Peporine Lopes |
| Support Opportunities: | BIOTA-FAPESP Program - Thematic Grants |