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.
Synthesis of two unnatural oxygenated aaptaminoids / G. Abbiati, A. Doda, M. Dell'Acqua, V. Pirovano, D. Facoetti, S. Rizzato, E. Rossi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 77:22(2012 Nov 16), pp. 10461-10467.
Synthesis of two unnatural oxygenated aaptaminoids
G. Abbiati
;A. DodaSecondo
;M. Dell'Acqua;V. Pirovano;D. Facoetti;S. RizzatoPenultimo
;E. RossiUltimo
2012
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.
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