One-pot synthesis of 3-hydroxyanthranilate derivatives using furans, bromoalkyne, and secondary amines. Issue 19 (6th May 2015)

• Record Type: Journal Article
• Authors: Shinohara, Hiroyuki; Sonoda, Motohiro; Hayagane, Naoya; Kita, Shota; Okushima, Shunsuke; Tanimori, Shinji; Ogawa, Akiya
• Is Part Of: Tetrahedron letters. Volume 56:Issue 19(2015)
• Page Start: 2500
• Page End: 2503
• Publication Date: 2015-05-06
• Subjects: Diels–Alder reaction -- Ring-opening aromatization -- 3-Hydroxyanthranilate -- One-pot synthesis -- Oxanorbornadiene; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.03.098
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A novel and convenient method for synthesizing 3-hydroxyanthranilate derivatives using furans, methyl 3-bromopropiolate, and secondary amines was developed. The synthetic reaction consisted of four steps: the Diels–Alder reaction, a conjugate addition reaction, dehydrobromination, and a ring-opening aromatization reaction. A plausible reaction pathway is described on the basis of the structures of the reaction intermediates. By using this method, sterically hindered 3-hydroxyanthranilate derivatives could be obtained selectively in good yields for four-steps.