Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/ure...

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Main Authors:	Paola Vitale, Luciana Cicco, Ilaria Cellamare, Filippo M. Perna, Antonio Salomone, Vito Capriati
Format:	Article
Language:	English
Published:	Beilstein-Institut 2020-08-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	deep eutectic solvents imidazoles phenacyl azides phenacyl halides pyrimidines
Online Access:	https://doi.org/10.3762/bjoc.16.158

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spelling	doaj-03ae58a1b572458aa599f62129a437112021-04-02T12:47:35ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-08-011611915192310.3762/bjoc.16.1581860-5397-16-158Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solventsPaola Vitale0Luciana Cicco1Ilaria Cellamare2Filippo M. Perna3Antonio Salomone4Vito Capriati5Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, ItalyDipartimento di Farmacia-Scienze del Farmaco, Università di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, ItalyDipartimento di Farmacia-Scienze del Farmaco, Università di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, ItalyDipartimento di Farmacia-Scienze del Farmaco, Università di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, ItalyDipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, 73100 Lecce, ItalyDipartimento di Farmacia-Scienze del Farmaco, Università di Bari “Aldo Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, ItalyWe report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et3N).https://doi.org/10.3762/bjoc.16.158deep eutectic solventsimidazolesphenacyl azidesphenacyl halidespyrimidines
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Paola Vitale Luciana Cicco Ilaria Cellamare Filippo M. Perna Antonio Salomone Vito Capriati
spellingShingle	Paola Vitale Luciana Cicco Ilaria Cellamare Filippo M. Perna Antonio Salomone Vito Capriati Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents Beilstein Journal of Organic Chemistry deep eutectic solvents imidazoles phenacyl azides phenacyl halides pyrimidines
author_facet	Paola Vitale Luciana Cicco Ilaria Cellamare Filippo M. Perna Antonio Salomone Vito Capriati
author_sort	Paola Vitale
title	Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_short	Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_full	Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_fullStr	Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_full_unstemmed	Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
title_sort	regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2020-08-01
description	We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et3N).
topic	deep eutectic solvents imidazoles phenacyl azides phenacyl halides pyrimidines
url	https://doi.org/10.3762/bjoc.16.158
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Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

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