2004
DOI: 10.3998/ark.5550190.0004.e19
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Synthesis of 3-azaharman and other new azacarbolines of the pyridazino[4,5-b]indole type

Abstract: Starting from the indole-fused pyridazinone 3, a series of new pyridazino [4,5-b]indoles, functionalized at positions 1, 2, or 5 was prepared, including the two tetracyclic compounds 12 and 13, which represent new ring systems. Reductive dehalogenation of the chloro compound 8 gave a 3-aza isoster of the natural product, harman.

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Cited by 2 publications
(1 citation statement)
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“…From 2-acetylindole-3-carboxylic acid. Haider et al 44 had done a modification on the procedure of preparation of pyridazino [4,5-b]indole 107 which was reported previously by Zhungietu et al 45 by condensation of 2-acetylindole-3-carboxylic acid 105 with hydrazine hydrate at elevated temperature. This reaction, however, suffers from poorly reproducible yields which reflect the high decarboxylation tendency of the starting material, causing a significant side reaction (formation of 2-acetylindole or its hydrazone, respectively).…”
Section: From 2-indolecarbohydrazidesmentioning
confidence: 99%
“…From 2-acetylindole-3-carboxylic acid. Haider et al 44 had done a modification on the procedure of preparation of pyridazino [4,5-b]indole 107 which was reported previously by Zhungietu et al 45 by condensation of 2-acetylindole-3-carboxylic acid 105 with hydrazine hydrate at elevated temperature. This reaction, however, suffers from poorly reproducible yields which reflect the high decarboxylation tendency of the starting material, causing a significant side reaction (formation of 2-acetylindole or its hydrazone, respectively).…”
Section: From 2-indolecarbohydrazidesmentioning
confidence: 99%