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

Shanmugaraju, Sankarasekaran; McAdams, Deirdre; Pancotti, Francesca; Hawes, Chris S.; Veale, Emma B.; Kitchen, Jonathan A.; Gunnlaugsson, Thorfinnur

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.

Citation

Shanmugaraju, S., McAdams, D., Pancotti, F., Hawes, C. S., Veale, E. B., Kitchen, J. A., & Gunnlaugsson, T. One-pot facile synthesis of 4-amino-1,8-naphthalimide derived Tröger's bases via a nucleophilic displacement approach. Organic and Biomolecular Chemistry, 15(35), 7321-7329. https://doi.org/10.1039/c7ob01835e

• Journal Article Type: Article
• Deposit Date: Jun 16, 2023
• Journal: Organic & Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 15
• Issue: 35
• Pages: 7321-7329
• DOI: https://doi.org/10.1039/c7ob01835e
• Keywords: Organic Chemistry; Physical and Theoretical Chemistry; Biochemistry
• Additional Information: : This document is Similarity Check deposited; : Supplementary Information; : Crystal Structure Data; : Sankarasekaran Shanmugaraju (ResearcherID); : Chris S. Hawes (ORCID); : Jonathan A. Kitchen (ResearcherID); : Thorfinnur Gunnlaugsson (ORCID); : The Royal Society of Chemistry has an exclusive publication licence for this journal; : Single-blind; : Received 25 July 2017; Accepted 14 August 2017; Accepted Manuscript published 14 August 2017; Advance Article published 22 August 2017; Version of Record published 13 September 2017