Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction

Research output: Contribution to journalArticle

1 Citation (Scopus)
22 Downloads (Pure)

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 languageEnglish
Pages (from-to)5925-5928
JournalDalton Transactions
Volume45
Issue number14
Early online date19 Aug 2015
DOIs
Publication statusPublished - 14 Apr 2016

Fingerprint

Carbodiimides
Kinetics
Magnesium
Substitution reactions
Derivatives

Cite this

Facile kinetic induction of a dihydropyridide to pyrrolide ring contraction. / Carbery, David R.; Hill, Michael S.; Mahon, Mary F.; Weetman, Catherine.

In: Dalton Transactions , Vol. 45, No. 14, 14.04.2016, p. 5925-5928.

Research output: Contribution to journalArticle

@article{9bfbcd58a8dc4a868ea9cc7ebe1f1349,
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",
year = "2016",
month = "4",
day = "14",
doi = "10.1039/C5DT02887F",
language = "English",
volume = "45",
pages = "5925--5928",
journal = "Dalton Transactions",
issn = "1477-9226",
publisher = "Royal Society of Chemistry",
number = "14",

}

TY - JOUR

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.

UR - http://dx.doi.org/10.1039/C5DT02887F

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 -