SYNTHESIS OF 8-SUBSTITUTED 12-METHYL-12H-IMIDAZO[4',5':2,3][1,4]DIAZEPINO[6,7,1-jk]CARBAZOLES

Kayed A.Abu Safieh; Fouad H.Darras; Mikdad T.Ayoub

首页> 外文期刊>Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry >SYNTHESIS OF 8-SUBSTITUTED 12-METHYL-12H-IMIDAZO[4',5':2,3][1,4]DIAZEPINO[6,7,1-jk]CARBAZOLES

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SYNTHESIS OF 8-SUBSTITUTED 12-METHYL-12H-IMIDAZO[4',5':2,3][1,4]DIAZEPINO[6,7,1-jk]CARBAZOLES

机译：合成8-取代的12-甲基-12H-咪唑并[4'，5'：2,3] [1,4]二氮杂[6,7,1-jk]咔唑

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A synthesis of model 8-substituted-12-methyl-12H-imidazo[4',5':2,3][1,4]-diazepino[6,7,1-jk]carbazoles (10a-c),based on the classical Bischler-Napieralski method,is described.Thus interaction of carbazole with 5-chloro-1-methyl-4-nitro-1H-imidazole (in the presence of sodium hydride) produced the corresponding 9-(1-methyl-4-nitro-1H-imidazole-5-yl)-9H-carbazole (7).Chemical reduction of the nitro group of 7 into the respective amino derivative 8,and subsequent acylation of the resulting amino group furnished the respective amides 9a-c.Cyclocondensation of the latter amides,using polyphosphoric acid under Bischler-Napieralski reaction conditions,delivered the target compounds 10a-c.The structures of these new pentacyclic heterocycles were supported by IR,MS,and NMR spectral data.

机译：基于模型8取代的12-甲基-12H-咪唑并[4'，5'：2,3] [1,4]-二氮杂[6,7,1-jk]咔唑（10a-c）的合成因此，咔唑与5-氯-1-甲基-4-硝基-1H-咪唑（在氢化钠存在下）的相互作用产生了相应的9-（1-甲基-4）。 -硝基-1H-咪唑-5-基）-9H-咔唑（7）。将7的硝基化学还原成相应的氨基衍生物8，随后酰化所得的氨基，得到相应的酰胺9a-c。后者的酰胺在Bischler-Napieralski反应条件下使用多磷酸进行环缩合，得到目标化合物10a-c。这些新的五环杂环的结构得到IR，MS和NMR光谱数据的支持。

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《Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry》 |2007年第12期|共8页
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Kayed A.Abu Safieh; Fouad H.Darras; Mikdad T.Ayoub;
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SYNTHESIS OF 8-SUBSTITUTED 12-METHYL-12H-IMIDAZO[4',5':2,3][1,4]DIAZEPINO[6,7,1-jk]CARBAZOLES

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