Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones

Lorenza Ghisu; Nicola Melis; Francesco Secci; Pierluigi Caboni; Massimiliano Arca; Régis Guillot; Thomas Boddaert; David J. Aitken; Angelo Frongia

doi:10.1039/C7OB02567J

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Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones†

Lorenza Ghisu,^a Nicola Melis,^a Francesco Secci,

^a Pierluigi Caboni,^b Massimiliano Arca,^a Régis Guillot,

^c Thomas Boddaert,

^c David J. Aitken

^c and Angelo Frongia

*^a

Author affiliations

* Corresponding authors

^a Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Complesso Universitario di Monserrato, S.S. 554, Bivio per Sestu, I-09042, Monserrato, Cagliari, Italy
E-mail: afrongia@unica.it

^b Dipartimento di Scienze della Vita e dell'Ambiente, Università degli Studi di Cagliari, Via Ospedale 72, Cagliari, Italy

^c CP3A Organic Synthesis Group and Services Communs, ICMMO – CNRS UMR 8182, Université Paris Sud, Université Paris Saclay, 15 rue Georges Clemenceau, 91405 Orsay cedex, France

Abstract

A two-step protocol is presented for the preparation of 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones from 2-hydroxycyclobutanone and some 2-aminopyridines via a catalyst-free synthesis of 2,2-bis(pyridin-2-ylamino)cyclobutanols followed by Dess–Martin periodinane mediated ring expansion.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/C7OB02567J
Article type: Communication
Submitted: 17 Oct 2017
Accepted: 08 Nov 2017
First published: 08 Nov 2017

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Org. Biomol. Chem., 2017,15, 9779-9784

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Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones

L. Ghisu, N. Melis, F. Secci, P. Caboni, M. Arca, R. Guillot, T. Boddaert, D. J. Aitken and A. Frongia, Org. Biomol. Chem., 2017, 15, 9779 DOI: 10.1039/C7OB02567J

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Organic & Biomolecular Chemistry

Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones†

Abstract

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Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones

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