Novel tricyclic diamines 3. Synthesis of 1, 4-diazaadamantane. Issue 8 (21st February 2018)

• Record Type: Journal Article
• Authors: McDonald, Ivar M.; Ng, Alicia
• Is Part Of: Tetrahedron letters. Volume 59:Issue 8(2018)
• Page Start: 755
• Page End: 759
• Publication Date: 2018-02-21
• Subjects: Diazaadamantane -- Tricyclic diamine -- Intramolecular alkylation -- Iminophosphorane; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.01.031
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Novel 1, 4-diazaadamantane was prepared. Synthesis relies on saturation of trisubstituted pyridine followed by intramolecular cyclization. Final ring closure appears to proceed via iminophosphorane displacement of a tosylate. Abstract: Synthesis of the previously unreported 1, 4-diazaadamantane is described. The overall strategy involves complete saturation of a flat, aromatic heterocycle, appropriate functionalization and intramolecular double alkylation. The alkylation takes place via an iminophosphorane under anhydrous conditions, which produced superior results vs. alkylation of the corresponding primary amine.