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Issue 14, 2016
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Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

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Abstract

Reactions between magnesium 1,4-dihydropyridide or 1,2-dihydro-iso-quinolide derivatives and carbodiimides, RN[double bond, length as m-dash]C[double bond, length as m-dash]NR, generally result in Mg–N insertion and formation of guanidinate complexes. More sterically perturbed systems with N-aryl carbodiimide substitution, however, follow a divergent course of reaction initiating heterocyclic ring contraction and pyrrolide formation under unprecedentedly mild conditions.

Graphical abstract: Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

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Article information


Submitted
27 Jul 2015
Accepted
19 Aug 2015
First published
19 Aug 2015

Dalton Trans., 2016,45, 5925-5928
Article type
Communication
Author version available

Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

D. R. Carbery, M. S. Hill, M. F. Mahon and C. Weetman, Dalton Trans., 2016, 45, 5925
DOI: 10.1039/C5DT02887F

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