title: Synthesis of two unnatural oxygenated aaptaminoids.
abstract: Two unprecedented oxygenated aaptaminoids have been synthesized starting from cheap and easily available 2,3-dihydroxybenzoic acid with the satisfactory overall yields of 31% and 34%. The key step of the procedure is the divergent thermic 5-exodig vs base-promoted 6-endodig cyclization of a 5-alkynylquinolinone derivative.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica A. Marchesini, Università degli Studi di Milano, via Venezian, 21, 20133 Milano, Italy. giorgio.abbiati@unimi.it
authors.forename: Giorgio
authors.initials: G
authors.lastname: Abbiati
authors.forename: Arjana
authors.initials: A
authors.lastname: Doda
authors.forename: Monica
authors.initials: M
authors.lastname: Dell'Acqua
authors.forename: Valentina
authors.initials: V
authors.lastname: Pirovano
authors.forename: Diego
authors.initials: D
authors.lastname: Facoetti
authors.forename: Silvia
authors.initials: S
authors.lastname: Rizzato
authors.forename: Elisabetta
authors.initials: E
authors.lastname: Rossi
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D062385:Hydroxybenzoates / Q000737:chemistry*; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D015363:Quinolones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D062385:Hydroxybenzoates; D009287:Naphthyridines; D015363:Quinolones; C009135:2,3-dihydroxybenzoic acid; C043986:aaptamine; D010100:Oxygen