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Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles
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Number of Authors: 10
2015 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 21, no 20, 7394-7398 p.Article in journal (Refereed) Published
Abstract [en]

A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a metal-free nitrene insertion, resulting in a new pyrrole ring. This novel synthetic approach has a wide substrate tolerance and it is applicable in the preparation of more complex drug-like molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic beta-aminophosphonate motif.

Place, publisher, year, edition, pages
2015. Vol. 21, no 20, 7394-7398 p.
Keyword [en]
aminophosphonate, boronate, cyclization, heterocycles, MIDA, nitrene
National Category
Chemical Sciences
URN: urn:nbn:se:su:diva-118363DOI: 10.1002/chem.201406549ISI: 000354027300015OAI: diva2:822196
Available from: 2015-06-16 Created: 2015-06-15 Last updated: 2015-06-16Bibliographically approved

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Eriksson, LarsStenmark, Pål
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Department of Materials and Environmental Chemistry (MMK)Department of Biochemistry and Biophysics
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