Work

Synthesis and meta -Amination of Pyridines via Multicomponent Cascade Reaction

Year: 2025

Type: article

Abstract: We report a green, multicomponent cascade synthesis of 3-aminopyridines via [1,3′-bipyridin]-1-ium intermediates undergoing Zincke aminolysis with ammonia supported by experimental evidence and DFT calculations. The method offers broad scope (>20 examples), good functional group tolerance, and scalability in batch and flow procedures. Synthetic utility is demonstrated through conversion into 3-halo, 3-hydroxy, and 3-thiopyridines, expanding the access to meta -substituted pyridines through peripheral editing of the unprotected amino group.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c03509

Authors: Telmo N. Francisco, Nuno R. Candeias, Samuel Guieu, Joana L. C. Sousa, Rafael F. A. Gomes, Carlos A. M. Afonso, Artur M. S. Silva, Hélio M. T. Albuquerque

Institutions: LAQV Requimte, University of Aveiro, Tampere University, University of Lisbon

Language: English

Topic: Multicomponent Synthesis of Heterocycles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Fundação para a Ciência e a Tecnologia, European Social Fund

Awards: G1198130363, G1795312437, Reinventing the chemistry of 3-formyl(chromones and quinolones) towards the synthesis of nitrobenzenes, pyridines and aza(xanthones and acridones), G349060782, Untitled, Funcionalização estéreo-seletiva e aumento de complexidade de ácido quínico por transferência de hidrogénio e oxidação, G4971484151

OpenAlex ID: W4415098846

FWCI: 1.751

Cites: 37

Cited by: 6

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