Synthesis of 1-substituted ellipticines by a new route to pyrido[4,3-b]carbazoles
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1706-1711
- https://doi.org/10.1039/p19790001706
Abstract
A new approach to pyrido[4,3-b]carbazole leading to 1-substituted ellipticines derivatives is described. A five-step synthesis starting from arenediazonium chlorides and 1-morpholinocyclohexenes gave 2-formyl-1-methyl-3,4-dihydrocarbazoles which were then aromatized by manganese dioxide to 2-formyl-1-methylcarbazoles. Knoevenagel malonic acid condensation afforded the corresponding trans-acrylic acids, the azides of which were cyclized in boiling diphenyl ether giving pyrido[4,3-b]carbazol-1 (2H)ones. These compounds were transfomed into 1-chlorojellipticines in boiling phosphorus oxychloride. Finally, the nucleophilic displacement of the chlorine atom by γ-diethylaminopropylamine provided the previously unknown 1-substituted pyrido[4,3-b]carbazoles.This publication has 3 references indexed in Scilit:
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