Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

David R. Carbery; Michael S. Hill; Mary F. Mahon; Catherine Weetman

doi:10.1039/C5DT02887F

Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

David R. Carbery, Michael S. Hill, Mary F. Mahon, Catherine Weetman

Research output: Contribution to journal › Article › peer-review

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Abstract

Reactions between magnesium 1,4-dihydropyridide or 1,2-dihydro-iso-quinolide derivatives and carbodiimides, RN=C=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.

Original language	English
Pages (from-to)	5925-5928
Journal	Dalton Transactions
Volume	45
Issue number	14
Early online date	19 Aug 2015
DOIs	https://doi.org/10.1039/C5DT02887F
Publication status	Published - 14 Apr 2016

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10.1039/C5DT02887F

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Group 2: Elements of 21st Century Catalysis
Hill, M.
Engineering and Physical Sciences Research Council
23/05/11 → 31/03/15
Project: Research council

MC2- Nuclear Magnetic Resonance (NMR)
Material and Chemical Characterisation (MC2)
Facility/equipment: Technology type
MC2- X-ray diffraction (XRD)
Material and Chemical Characterisation (MC2)
Facility/equipment: Technology type

Cite this

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title = "Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction",

abstract = "Reactions between magnesium 1,4-dihydropyridide or 1,2-dihydro-iso-quinolide derivatives and carbodiimides, RN=C=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.",

author = "Carbery, {David R.} and Hill, {Michael S.} and Mahon, {Mary F.} and Catherine Weetman",

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journal = "Dalton Transactions ",

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T1 - Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

AU - Carbery, David R.

AU - Hill, Michael S.

AU - Mahon, Mary F.

AU - Weetman, Catherine

PY - 2016/4/14

Y1 - 2016/4/14

N2 - Reactions between magnesium 1,4-dihydropyridide or 1,2-dihydro-iso-quinolide derivatives and carbodiimides, RN=C=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.

AB - Reactions between magnesium 1,4-dihydropyridide or 1,2-dihydro-iso-quinolide derivatives and carbodiimides, RN=C=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.

U2 - 10.1039/C5DT02887F

DO - 10.1039/C5DT02887F

M3 - Article

VL - 45

SP - 5925

EP - 5928

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 14

ER -

Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

Abstract

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Projects

Group 2: Elements of 21st Century Catalysis

Equipment

MC2- Nuclear Magnetic Resonance (NMR)

MC2- X-ray diffraction (XRD)

Cite this