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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Charting the Chemical Reactivity Space of 2,3-Substituted Furo[2,3-b]pyridines Synthesized via the Heterocyclization of Pyridine-N-oxide Derivatives

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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: 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 type: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 15/06588-5 - Development of library of heterocyclic fragments based on new heteroaromatic cores
Grantee:Fernando Fumagalli
Support type: Scholarships in Brazil - Doctorate