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• W2952134103 abstract "Condensation of 1-methyl-β-carboline-3-carbaldehyde with ethyl azidoacetate and subsequent thermolysis of the resulting azidopropenoate was used to [c] annulate a pyrrole ring onto the β-carboline moiety, thus producing the first example of the pyrrolo[3,2-c]-β-carboline ring system. The latter ring system results from cyclization at the C-4 carbon, whereas cyclization at the N-2 nitrogen atom also occurs to form a pyrazolo[3,2-c]-β-carboline ring system. Condensation of β-carboline-1-carbaldehyde with ethyl azidoacetate produced a non-isolable intermediate, which immediately underwent cyclization, however in this case cyclization occurred via attack at the ester and the azide remained intact. The resulting 5-azidocanthin-6-one was transformed to the first examples of 5-aminocanthin-6-ones. β-Carboline-1,3-dicarbaldehyde failed to give an acceptable reaction with ethyl azidoacetate, but did undergo selective condensation with dimethyl acetylene dicarboxylate at the C-1 carbaldehyde with concomitant cyclization to form a highly functionalized 2-formyl-canthine derivative." @default.
• W2952134103 created "2019-06-27" @default.
• W2952134103 creator A5066897346 @default.
• W2952134103 creator A5047014395 @default.
• W2952134103 date "2004-07-01" @default.
• W2952134103 modified "2023-10-09" @default.
• W2952134103 title "Synthesis of some fused β-carbolines including the first example of the pyrrolo[3,2-<i>c</i>]-β-carboline system" @default.
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• W2952134103 doi "https://doi.org/10.1002/jhet.5570410409" @default.
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