Pyrido acridines, synthesis

Heterocyclic compounds which have, as a common structural feature, a tetracyclic pyrido[2,3,4-k/ acridine system often offer striking biological activities such as antitumor activities. Specifically, a facile synthesis of ascididemine (70) was achieved by high-pressure IEDAR of 6H-4-bromopyrido[2,3,4-/d]acridin-6-one (69) with propanal dimethylhydrazone... 

Synthesis of 7//-pyrido[2,3,4-/c/]acridines related to marine alkaloids 92H(34)2385. 

A new synthesis was developed by Y. Kashman et al. for the preparation of the parent pyrido[2,3,4-/c/]acridine skeleton utilizing the Doebner-Miller synthesis. In the first step, 3-aminoacetanilide was reacted with vinyl phenyl ketone in the presence of m-nitrobenzenesulfonic acid sodium salt and acetic acid to afford the corresponding 4-phenylquinolines. The acetamide group was then converted to the corresponding aryl azide, which underwent intramolecular nitrene insertion upon thermolysis to give the desired heterocyclic skeleton. 

Gellerman, G., Rudi, A., Kashman, Y. Synthesis of pyrido[2,3,4-kl]acridines. A building block for the synthesis of pyridoacridine alkaloids. Tetrahedron Lett. 1992, 33, 5577-5580. 

The synthesis of some hexa- and heptacyclic molecules 24 and 25 containing a pyrido[3,2-fl]acridine nucleus has been reported, the principal step being the ring closure of anthraquinone-derived precursors 22 and 23 (Scheme 6) (84KGS962). 

Once again, we have used the strategy developed for the synthesis of pyrido[2,3-c]acridines to prepare furo[2,3-c]acridines 362 (96TH1). 

Gellerman, G., Rudi, A. and Kashman, Y. 1994. The biomimetic synthesis of marine alkaloid related pyrido- and pyrrolo[2,3,4-Al]acridines. Tetrahedron 50(45) 12959-12972. 

Radchenko, O.S., Balaneva, N.N., Denisenko, V.A., and Novikov, V.L. (2006) A simple and effective approach to the synthesis of pyrido [4,3,2-mn]pyrrolo[3,2,l-de]acridine skeleton of amoamines A and B, pentacyclic marine alkaloids from the asddian Cystodytes sp.. Tetrahedron Lett., 47, 7819-7822. 

Blanco, M.D., Avendano, C., and Menendez, J.C. (1999) Concise synthesis of tetrahydro derivatives of the pyrido[2,3-b]acridine and pyrido[3,2-b]acridine ring systems. Tetrahedron, 55,12637-12646. 

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