One-pot synthesis of 3-hydroxyanthranilate derivatives using furans, bromoalkyne, and secondary amines

• Published in: Tetrahedron letters Vol. 56; no. 19; pp. 2500 - 2503
• Main Authors: Shinohara, Hiroyuki, Sonoda, Motohiro, Hayagane, Naoya, Kita, Shota, Okushima, Shunsuke, Tanimori, Shinji, Ogawa, Akiya
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 06.05.2015; Elsevier
• Subjects: 3-Hydroxyanthranilate; Chemistry; Chemistry, Organic; Diels–Alder reaction; One-pot synthesis; Oxanorbornadiene; Physical Sciences; Ring-opening aromatization; Science & Technology; One-pot synthesis; 3-Hydroxyanthranilate; Ring-opening aromatization; Diels–Alder reaction; Oxanorbornadiene; CONVENIENT SYNTHESIS; DESIGN; Oxanorbomadiene; REARRANGEMENT; ACID-DERIVATIVES; RING; BIOSYNTHESIS; EXPLORATION; Diels-Alder reaction; ACCESS; ALKALOIDS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2015.03.098

[Display omitted] 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.