Copper-Catalyzed C–N Bond Formation via C–H Functionalization: Facile Synthesis of Multisubstituted Imidazo[1,2-a]pyridines from N-(2-Pyridinyl)enaminones

Sandro Cacchi; Alessia Ciogli; Nicola Demitri; Giancarlo Fabrizi; Francesca Ghirga; Antonella Goggiamani; Antonia Iazzetti; Doriano Lamba

doi:10.1055/s-0037-1610071

Synthesis, Table of Contents

Synthesis 2018; 50(17): 3513-3519
DOI: 10.1055/s-0037-1610071

paper

Copper-Catalyzed C–N Bond Formation via C–H Functionalization: Facile Synthesis of Multisubstituted Imidazo[1,2-a]pyridines from N-(2-Pyridinyl)enaminones

Sandro Cacchi

^aDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy Email: antonia.iazzetti@uniroma1.it

,

Alessia Ciogli

^aDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy Email: antonia.iazzetti@uniroma1.it

,

Nicola Demitri

^bElettra-Sincrotrone Trieste, S.S. 14 Km 163.5 in Area Science Park, 34149 Basovizza, Trieste, Italy

,

Giancarlo Fabrizi

^aDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy Email: antonia.iazzetti@uniroma1.it

,

Francesca Ghirga

^cCenter for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Viale Regina Elena 291, 00161 Rome, Italy

,

Antonella Goggiamani

^aDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy Email: antonia.iazzetti@uniroma1.it

,

Antonia Iazzetti*

^aDipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, 00185 Rome, Italy Email: antonia.iazzetti@uniroma1.it

,

Doriano Lamba

^dIstituto di Cristallografia–CNR, S.S. 14 Km 163.5 in Area Science Park, 34149 Basovizza, Trieste, Italy

› Author Affiliations

Abstract

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Abstract

An efficient, new copper-catalyzed approach to the construction of the multisubstituted imidazo[1,2-a]pyridine skeleton from N-(2-pyridinyl)enaminones has been developed.

Key words

copper - enaminones - imidazo[1,2-a]pyridines - cyclization - C–N bond formation - C–H functionalization

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References

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14a The structure of 2a, and that of all the other cyclization products, was indirectly confirmed by an X-ray crystal structure analysis of 2m. CCDC 1819911 (2m) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

Supplementary Material

Supporting Information