Synthesis of 3-substituted benzo [g] isoquinoline-5, 10-diones: a convenient one-pot Sonogashira coupling/iminoannulation procedure

S Van Aeken, S Verbeeck, J Deblander, BUW Maes…

Index: Van Aeken, Sam; Verbeeck, Stefan; Deblander, Jurgen; Maes, Bert U.W.; Abbaspour Tehrani, Kourosch Tetrahedron, 2011 , vol. 67, # 12 p. 2269 - 2278

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Citation Number: 5

Abstract

A series of 3-substituted 5, 10-dimethoxybenzo [g] isoquinolines were prepared by coupling of terminal alkynes with the tert-butylimine of 3-bromo-1, 4-dimethoxy-2-naphthaldehyde in the presence of a Pd-catalyst and subsequent Cu-catalyzed cyclization of the intermediate 3- alkynyl-2-naphthylcarbaldehyde. A CAN-mediated oxidative demethylation yielded the corresponding 2-azaanthraquinones in excellent yields. Since this methodology proved to ...