Metal-free new synthesis of 1, 3-naphthoxazines via intramolecular cross dehydrogenative-coupling reaction of 1-(α-aminoalkyl)-2-naphthols using hypervalent iodine(III) reagent. Issue 6 (10th February 2016)

• Record Type: Journal Article
• Authors: Waghmode, Nitin A.; Kalbandhe, Amit H.; Thorat, Prerana B.; Karade, Nandkishor N.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 6(2016)
• Page Start: 680
• Page End: 683
• Publication Date: 2016-02-10
• Subjects: Betti reaction -- Hypervalent iodine reagents -- Cross dehydrogenative-coupling (CDC) -- 1, 3-Naphthoxazines -- Imminium ion; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.12.117
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A series of 1-(α-aminoalkyl)-2-naphthols were synthesized via three-component Betti reaction of β-naphthol, aldehyde, and cyclic secondary amine under reflux conditions. The subsequent reactions of 1-(α-aminoalkyl)-2-naphthols with (diacetoxyiodo)benzene resulted in the formation of 1, 3-napthoxazines. This reaction demonstrates the formation of CO bond via cross dehydrogenative-coupling (CDC) under transition metal-free conditions.