- A simple way to some sophisticated fused nitrogen heterocycles
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Selected nitroarenes were found to react with arylmethylene compounds prone to form benzylic-type carbanion to give fused nitrogen heterocycles in the presence of silylating agent.
- Wróbel, Zbigniew
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- Efficient formation of σH-adducts as a key step in the synthesis of acridines via Lewis acid-promoted transformations of the nitro group
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A step-by-step methodology was applied in the Lewis acid-promoted synthesis of fused heterocyclic systems from carbanions and nitroarenes. Efficient formation of σH-adducts of substituted nitrobenzenes and phenylacetonitrile derivatives followed by reductive transformation of the nitro group with silylating or acylating agents leads to 9-cyanoacridines. The method was found to be superior to the earlier one-pot approach, resulting in better yields and a broader scope of the reaction.
- Bobin, Mariusz,Kwast, Andrzej,Wróbel, Zbigniew
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p. 11048 - 11054
(2008/02/12)
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- REACTION OF 4-CHLORO-1-NITROBENZENE WITH o-SUBSTITUTED PHENYLACETONITRILES; SYNTHESIS OF 8-CHLORO-1-METHYL(AND METHYLTHIOMETHYL)-6-(2-SUBSTITUTED PHENYL)-4H-s-TRIAZOLO-1,4-BENZODIAZEPINES
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Reactions of 4-chloro-1-nitrobenzene with 2-methyl-, 2-methoxy- and 2-(methylthio)phenylacetonitrile in methanolic potassium hydroxide gave mixture from which the excepted 3-aryl-5-chloro-2,1-benzisoxazoles Ia-c were isolated in addition to the 2H-indoles IIIa and IIIc and acridines VIII and IX.The 2,1-benzisoxazoles were reduced to the 2-aminobenzophenones XIIa-c which were transformed via the phthalimidoacetamido compounds XIIIa-c to 5-aryl-7-chloro-1,3-dihydro-1,4-benzodiazepine-2-ones XVa-c.Treatment with phosphorus pentasulfide led to the thiones XVIa-c which reacted in boiling butanol either with acetohydrazide or with (methylthio)acetohydrazide to give the title compounds XVIIa-c and XVIIIa-c.They showed only weak anticonvulsant, incoordinating and central depressant effects.
- Vejdelek, Zdenek,Holubek, Jiri,Ryska, Miroslav,Koruna, Ivan,Svatek, Emil,et.al.
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p. 2545 - 2563
(2007/10/02)
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