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

Pure And Applied Chemistry

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

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5925-5928
Number of pages	4
Journal	Dalton Transactions
Volume	2016
Issue number	45
DOIs	https://doi.org/10.1039/C5DT02887F
Publication status	Published - 1 Jan 2016

Keywords

dihydropyridide
facile kinetic induction

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10.1039/C5DT02887F

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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[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.",

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

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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 - 2016/1/1

Y1 - 2016/1/1

N2 - 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.

AB - 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.

KW - dihydropyridide

KW - facile kinetic induction

U2 - 10.1039/C5DT02887F

DO - 10.1039/C5DT02887F

M3 - Article

SN - 1477-9226

VL - 2016

SP - 5925

EP - 5928

JO - Dalton Transactions

JF - Dalton Transactions

IS - 45

ER -

Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

Abstract

Keywords

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