Pyrido 3 ,4 :4,5 pyrrolo isoquinolines

The importance of azaellipticines is illustrated by the fact that 204 (BD-40) is undergoing clinical trials 10,98). Using their new 1-chloroellipticine synthesis (Scheme 20), Bisagni et al. 74) have described an extremely concise route to 10-chloro-5,6-dimethyl-5ff-pyrido[3, 4 4,5]pyrrolo[2,3-g]isoquinoline (208) and the side-chain amine derivatives 209-211 (Scheme 35). Formylation of 1-methyl -5-azaindole (205), followed by reaction with the lithiochloropyridine 124, gave... 

Treatment of N-2,4-dinitrophenylpyridinium chloride (778) with phenyl-hydrazine in acetic acid causes reductive cyclization to yield the pyrido[l,2-ajimidazole (779). 3-Aminocrotononitrile, MeC(NH2)=CHCN, condenses with quinoline 1-oxide and isoquinoline 2-oxide to form the tricyclic compounds (780) and (781), respectively." The imidazo[5,l-a]isoquinoline derivative (783) is obtained by the action of phenyl isothiocyanate on the sodium salt of the Reissert compound (782)." ° Triethyl phosphite reduces the o-nitrophenyldipyr-rolylmethane (784 R=N02) to the nitrene (784 R = N), which forms the pyrrolo[3,2-6]quinoline derivative (785) by an intramolecular insertion reac-tion." 3-Amino-177-isoindole (786) reacts with acetylacetone in the presence of perchloric acid to yield the pyrimidoisoindolium salt (787). ... 

In addition to carbazoles, pyrrole ring-containing PAHs such as 7/f-indolo[2,3-clquinoline 9,1 l//-indolo[3,2-c]isoquinoline 11, 9/7-pyrrolo[2,3- 4,5-c ]dipyridine 13a, 9/7-pyrido[2,3- ]indole 13b, benzo[a]pyrrolo[3,4-c]carbazole-l,3-(2//,8//)-dione 15, and 6//-indolo[3,2-fe]benzo[fe]thiophene 17 were accessible by intramolecular direct arylation strategy (Scheme 22.4) [10]. The cyclization of 3-(2-bromophenylamino)quinoline 8 and 4-(2-bromophenylamino)isoquinoline 10 was catalyzed by Pd(PPh3)2Cl2 in the presence of NaOAc in DMA and reached to... 

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