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Issue 2, 2018
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Three successive and regiocontroled palladium cross-coupling reactions to easily synthesize novel series of 2,4,6-tris(het)aryl pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyrimidines

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Abstract

The first access to tris(het)arylated pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyrimidine derivatives is reported. The series were generated from 4-chloroaminopyridinium, which afforded the key intermediate bearing three leaving groups, i.e. a C-2 methylsulfanyl, a lactame carbonyl group in C-4 and a chlorine atom in C-6. The regioselective reactions led to the tris(het)aryl derivatives with satisfying to high yields. The three successive cross-coupling reactions occurred first in C-6 by the displacement of chlorine, next in C-4 position by a sequential Pd-catalyzed phosphonium coupling and finally in C-2 under a Pd/Cu-catalyzed desulfitative cross-coupling reaction. The optimization and scope of each reaction are discussed and the original compounds characterized.

Graphical abstract: Three successive and regiocontroled palladium cross-coupling reactions to easily synthesize novel series of 2,4,6-tris(het)aryl pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyrimidines

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Publication details

The article was received on 08 Nov 2017, accepted on 18 Dec 2017 and first published on 02 Jan 2018


Article type: Paper
DOI: 10.1039/C7RA12246B
Citation: RSC Adv., 2018,8, 732-741
  • Open access: Creative Commons BY-NC license
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    Three successive and regiocontroled palladium cross-coupling reactions to easily synthesize novel series of 2,4,6-tris(het)aryl pyrido[1′,2′:1,5]pyrazolo[3,4-d]pyrimidines

    R. Belaroussi, A. Ejjoummany, A. El Hakmaoui, M. Akssira, G. Guillaumet and S. Routier, RSC Adv., 2018, 8, 732
    DOI: 10.1039/C7RA12246B

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