Abstract
By using the Suzuki-Miyaura protocol, a simple straightforward synthesis of functionalized 2-arylaziridines has been developed. By means of this synthetic strategy from readily available ortho-, meta- and para-bromophenylaziridines and aryl- or heteroarylboronic acids, new aziridines could be obtained. The cross-coupling reactions occurred without ring opening of the three membered ring. Preliminary results on the antimicrobial activity of the heterosubstituted biaryl compounds have been also included.
Highlights
The importance of aziridines as useful building blocks in organic chemistry has been extensively recognized over the past decades [1,2,3,4,5,6,7,8]
In previous works we have reported that nitrogen-bearing small heterocycles, such as aziridine and azetidines, could promote the direct C-H ortho-metallation of the aryl ring [30,31], acting as a directing metallation group (DMG) [32,33]
With the aim to verify this “ortho-effect” of the aziridine ring and set-up a procedure for the preparation of functionalized arylaziridines, we investigated the lithiation-borylation sequence in the meta and para positions of the aromatic ring of N-alkyl-2-arylaziridines
Summary
The importance of aziridines as useful building blocks in organic chemistry has been extensively recognized over the past decades [1,2,3,4,5,6,7,8]. Aziridines are interesting structural fragments in bioactive compounds and their pharmacological activity is often strictly related to the reactivity of the spring-loaded aziridine functionality [24,25,26], for example by Molecules 2014, 19 endogenous nucleophiles. Due to their extensive use in organic and medicinal chemistry, several methodologies for the preparation of useful functionalized aziridines have been developed. N-alkyl-2-arylaziridines could be obtained from readily available 2-aryloxiranes (path a) by a ring opening reaction, using primary amine, followed by a cyclization under Mitsunobu conditions [27]
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