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

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

1 Citation (Scopus)

447 Downloads (Pure)

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. (Principal Investigator), Tuttle, T. (Co-investigator) & McMahon, C. (Research Co-investigator)
EPSRC (Engineering and Physical Sciences Research Council)
1/10/19 → 28/06/24
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",

language = "English",

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T1 - A study of the reactivity of cyclic aminomethylammonium mannich salts

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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