Synthesis 2022; 54(16): 3658-3666
DOI: 10.1055/s-0041-1738070
paper

One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones

Yurii V. Ostapiuk
a   Ivan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
,
Mary Y. Ostapiuk
a   Ivan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
,
Oksana V. Barabash
a   Ivan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
,
Mykola Kravets
b   Institute of Physical Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
,
Colin Herzberger
c   Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany
,
Jan C. Namyslo
c   Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany
,
Mykola D. Obushak
a   Ivan Franko National University of Lviv, Department of Organic Chemistry, Kyryla i Mefodiya Str. 6, 79005 Lviv, Ukraine
,
c   Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, 38678 Clausthal-Zellerfeld, Germany
› Institutsangaben
The authors thank the National Research Foundation of Ukraine (Project 2020.01/0166 ‘New azole and cage-like agents against cancer and pathogenic microorganisms’).


Abstract

Both one-pot and two-step procedures for the synthesis of substituted 2-aminothiazoles and 2-aminoselenazoles are described. Anilines are first converted into arenediazonium bromides, which are then reacted with methyl vinyl ketone or cyclopropyl vinyl ketone in the presence of copper(II) bromide to give 4-aryl-3-bromobutan-2-ones (40–71%) and 3-aryl-2-bromo-1-cyclopropylpropan-1-ones (41–79%), respectively. These products are reacted, without prior isolation, with thiourea or selenourea to prepare 4-methyl- and 4-cyclopropyl-5-(R-benzyl)thiazol-2-amines (14 examples) and their selenium analogs (14 examples). The yields of the one-pot procedure are higher (40–81%) than those of the two-step procedure (32–70%).

Supporting Information



Publikationsverlauf

Eingereicht: 02. März 2022

Angenommen nach Revision: 28. März 2022

Artikel online veröffentlicht:
03. Mai 2022

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