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One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tröger's bases via a nucleophilic displacement approach

One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tröger's bases via a nucleophilic displacement approach
One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tröger's bases via a nucleophilic displacement approach
We report here a novel one-pot synthetic strategy for the synthesis of a family of N-alkyl-1,8-naphthalimide based Tröger's bases via a nucleophilic substitution reaction of a common ‘precursor’ (or a ‘synthon’) N-aryl-1,8-naphthalimide Tröger's base heated at 80 °C in neat aliphatic primary amine, in overall yield of 65–96%. This methodology provides an efficient and one-step facile route to design 1,8-naphthalimide derived Tröger's base structures in analytically pure form without the use of column chromatography purification, that can be used in medicinal chemistry and as supramolecular scaffolds. We also report the formation of the corresponding anhydride, and the crystallographic analysis of two of the resulting products, that of the N-phenyl-4-amino-1,8-naphthalimide and the anhydride derived Tröger's bases.
1477-0520
7321-7329
Shanmugaraju, Sankarasekaran
193c398c-9ba6-4bc4-8204-ae483b9f9fda
Mcadams, Deirdre
d658aa00-5db6-403d-9735-e448f56eb07d
Pancotti, Francesca
acd90cde-0c00-4f78-a1d8-36fe5f0c4833
Hawes, Chris S.
c3d2ccc1-40e2-4bf7-9eef-b4bfe8b8af20
Veale, Emma B.
92576e03-2cf9-48fc-80f2-9907e7331390
Kitchen, Jonathan A.
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Gunnlaugsson, Thorfinnur
bbfcaaa6-2aca-47c9-9b7b-954442218f50
Shanmugaraju, Sankarasekaran
193c398c-9ba6-4bc4-8204-ae483b9f9fda
Mcadams, Deirdre
d658aa00-5db6-403d-9735-e448f56eb07d
Pancotti, Francesca
acd90cde-0c00-4f78-a1d8-36fe5f0c4833
Hawes, Chris S.
c3d2ccc1-40e2-4bf7-9eef-b4bfe8b8af20
Veale, Emma B.
92576e03-2cf9-48fc-80f2-9907e7331390
Kitchen, Jonathan A.
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Gunnlaugsson, Thorfinnur
bbfcaaa6-2aca-47c9-9b7b-954442218f50

Shanmugaraju, Sankarasekaran, Mcadams, Deirdre, Pancotti, Francesca, Hawes, Chris S., Veale, Emma B., Kitchen, Jonathan A. and Gunnlaugsson, Thorfinnur (2017) One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tröger's bases via a nucleophilic displacement approach. Organic & Biomolecular Chemistry, 15 (35), 7321-7329. (doi:10.1039/C7OB01835E).

Record type: Article

Abstract

We report here a novel one-pot synthetic strategy for the synthesis of a family of N-alkyl-1,8-naphthalimide based Tröger's bases via a nucleophilic substitution reaction of a common ‘precursor’ (or a ‘synthon’) N-aryl-1,8-naphthalimide Tröger's base heated at 80 °C in neat aliphatic primary amine, in overall yield of 65–96%. This methodology provides an efficient and one-step facile route to design 1,8-naphthalimide derived Tröger's base structures in analytically pure form without the use of column chromatography purification, that can be used in medicinal chemistry and as supramolecular scaffolds. We also report the formation of the corresponding anhydride, and the crystallographic analysis of two of the resulting products, that of the N-phenyl-4-amino-1,8-naphthalimide and the anhydride derived Tröger's bases.

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Accepted/In Press date: 14 August 2017
e-pub ahead of print date: 14 August 2017
Published date: 21 September 2017

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Local EPrints ID: 414810
URI: http://eprints.soton.ac.uk/id/eprint/414810
ISSN: 1477-0520
PURE UUID: 0586c0ce-6066-4374-a937-7e1a1c3258c2
ORCID for Jonathan A. Kitchen: ORCID iD orcid.org/0000-0002-7139-5666

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Date deposited: 11 Oct 2017 16:31
Last modified: 07 Oct 2020 04:24

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Contributors

Author: Sankarasekaran Shanmugaraju
Author: Deirdre Mcadams
Author: Francesca Pancotti
Author: Chris S. Hawes
Author: Emma B. Veale
Author: Jonathan A. Kitchen ORCID iD
Author: Thorfinnur Gunnlaugsson

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