Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles
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
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.
aminophosphonate, boronate, cyclization, heterocycles, MIDA, nitrene
IdentifiersURN: urn:nbn:se:su:diva-118363DOI: 10.1002/chem.201406549ISI: 000354027300015OAI: oai:DiVA.org:su-118363DiVA: diva2:822196