Pyrrolo acridine

Heating either the dimedonylmethane 377 or 9-aroyl-octahydro-xanthene 58 with ammonia at 130-150 °C led to the formation of pyrrolo-acridine 378. But, at lower temperature, 90-120 °C, the tetrahydroindoles 379 were initially formed which can be converted to 378 (88CHE417) (Scheme 77). 

In a subsequent investigation by the author (1) antineoplastic agents consisting of pyrrolo [2,1 -c] [ 1,4]benzodiazepine acridone, (I), and acridine hybrids were prepared which were effective against leukemia, nonsmall cell, lung, and colon cancers. 

We have prepared pyrrolo[2,3-c]acridines 304 by our standard method, involving the base-catalyzed cyclization of the enamines 303, followed by oxidation (Scheme 56) (96TH1). 

Gellerman et al. (94T12959) have described the biomime tic synthesis of a pyrrolo[2,3,4-k/]acridine 305 (Scheme 57). 

Bilgic and Young have reported the formation of the benzo[ ]pyrrolo[2,3-h]acridine 294 in a reaction between 1-(Y, Y-dimethylaminomethyl)naphth-2-ol 292 and 5-aminoindole. A quinone methide 293 is believed to be involved as an intermediate (Scheme 52). The reaction of the naphthol 292 with 5-aminoindazole gave the angular pyrazoloacridine 295 [80JCS(P1) 1233]. 

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. 

A domino approach for the synthesis of pyrrolo[2,3,4-W]acridin-l-ones via a C-N bond cleavage reaction has been reported (Scheme 187). " ... 

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