A study of the reactivity of cyclic aminomethylammonium mannich salts

Daniela Dimitrova; Connor McMahon; Alan R. Kennedy; John A. Parkinson; Stuart G. Leach; Lee T. Boulton; David D. Pascoe; John A. Murphy

doi:10.1016/j.tet.2022.133120

A study of the reactivity of cyclic aminomethylammonium mannich salts

Daniela Dimitrova, Connor McMahon, Alan R. Kennedy, John A. Parkinson, Stuart G. Leach, Lee T. Boulton, David D. Pascoe, John A. Murphy

Pure And Applied Chemistry

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Abstract

A novel method for the preparation of aminoalkylaminomethyl products was developed utilising novel Mannich-type salts featuring a R ₂NCH ₂NR ₃ ⁺ moiety. This methodology showed good nucleophile scope and was successfully employed in reactions under basic, acidic, and neutral conditions. A wide range of diamine products was successfully synthesised, including a neuropeptide Y antagonist.

Original language	English
Article number	133120
Number of pages	17
Journal	Tetrahedron
Volume	128
Early online date	5 Nov 2022
DOIs	https://doi.org/10.1016/j.tet.2022.133120
Publication status	Published - 3 Dec 2022

Keywords

Mannich salts
trialkylamine
nucleophile
amminomethylammonium
functionalisation

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10.1016/j.tet.2022.133120Licence: CC BY 4.0

Dimitrova-etal-Tetrahedron-2022-A-study-of-the-reactivity-of-cyclic-aminomethylammonium-mannich-saltsFinal published version, 1.09 MBLicence: CC BY 4.0

Industrial Case Account - University of Strathclyde 2019 | McMahon, Connor
Murphy, J., Tuttle, T. & McMahon, C.
EPSRC (Engineering and Physical Sciences Research Council)
1/10/19 → 1/10/23
Project: Research Studentship Case - Internally allocated

Cite this

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title = "A study of the reactivity of cyclic aminomethylammonium mannich salts",

abstract = "A novel method for the preparation of aminoalkylaminomethyl products was developed utilising novel Mannich-type salts featuring a R 2NCH 2NR 3 + moiety. This methodology showed good nucleophile scope and was successfully employed in reactions under basic, acidic, and neutral conditions. A wide range of diamine products was successfully synthesised, including a neuropeptide Y antagonist.",

keywords = "Mannich salts, trialkylamine, nucleophile, amminomethylammonium, functionalisation",

author = "Daniela Dimitrova and Connor McMahon and Kennedy, {Alan R.} and Parkinson, {John A.} and Leach, {Stuart G.} and Boulton, {Lee T.} and Pascoe, {David D.} and Murphy, {John A.}",

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doi = "10.1016/j.tet.2022.133120",

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AU - Dimitrova, Daniela

AU - McMahon, Connor

AU - Kennedy, Alan R.

AU - Parkinson, John A.

AU - Leach, Stuart G.

AU - Boulton, Lee T.

AU - Pascoe, David D.

AU - Murphy, John A.

PY - 2022/12/3

Y1 - 2022/12/3

N2 - A novel method for the preparation of aminoalkylaminomethyl products was developed utilising novel Mannich-type salts featuring a R 2NCH 2NR 3 + moiety. This methodology showed good nucleophile scope and was successfully employed in reactions under basic, acidic, and neutral conditions. A wide range of diamine products was successfully synthesised, including a neuropeptide Y antagonist.

AB - A novel method for the preparation of aminoalkylaminomethyl products was developed utilising novel Mannich-type salts featuring a R 2NCH 2NR 3 + moiety. This methodology showed good nucleophile scope and was successfully employed in reactions under basic, acidic, and neutral conditions. A wide range of diamine products was successfully synthesised, including a neuropeptide Y antagonist.

KW - Mannich salts

KW - trialkylamine

KW - nucleophile

KW - amminomethylammonium

KW - functionalisation

U2 - 10.1016/j.tet.2022.133120

DO - 10.1016/j.tet.2022.133120

M3 - Article

SN - 0040-4020

VL - 128

JO - Tetrahedron

JF - Tetrahedron

M1 - 133120

ER -

A study of the reactivity of cyclic aminomethylammonium mannich salts

Abstract

Keywords

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Projects

Industrial Case Account - University of Strathclyde 2019 | McMahon, Connor

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