Synthesis 2019; 51(04): 933-943
DOI: 10.1055/s-0037-1610666
paper
© Georg Thieme Verlag Stuttgart · New York

Imidazole-Fused Enediynes by Selective C5–C4 Alkynylations of 4,5-Dibromoimidazoles

Marco Lessi
a  Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: fabio.bellina@unipi.it
,
Alessandro Panattoni
b  Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead & IOCB Research Center, 16610 Prague 6, Czech Republic
,
Luca Guglielmero
a  Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: fabio.bellina@unipi.it
c  Scuola Normale Superiore, Piazza dei Cavalieri 7, 56126 Pisa, Italy
,
Pierpaolo Minei
a  Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: fabio.bellina@unipi.it
,
a  Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy   Email: fabio.bellina@unipi.it
› Author Affiliations
This work was supported by the Regione Toscana under POR-CREO 2014-2020 (project ‘COOLSUN’), the Università di Pisa under PRA 2017 (project No. PRA_2017_28).
Further Information

Publication History

Received: 18 August 2018

Accepted after revision: 01 October 2018

Publication Date:
30 October 2018 (eFirst)

Abstract

An efficient synthesis of symmetrical 1,2-disubstituted 4,5-dialkynylimidazoles by Sonogashira alkynylation of the corresponding 4,5-dibromo derivatives was developed. Moreover, through a careful tuning of the palladium ligand, unsymmetrical 1,2-disusbtituted 4,5-dialkynylimidazoles were also prepared through a regioselective C5 alkynylation of 4,5-dibromoimidazoles, followed by a second alkynylation involving the 4-bromo derivatives so obtained. This interesting class of imidazole-fused enediynes is also able to give thermal Bergman cycloaromatization (BC), as proved by DSC experiments.

Supporting Information

 
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