The Synthesis of Heterocyclic Compounds from Aryl Azides. II. Carbolines and Thienoindole1
The Synthesis of Heterocyclic Compounds from Aryl Azides. II. Carbolines and Thienoindole1
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从芳基叠氮化物合成杂环化合物。
DOI：
10.1021/ja01150a061
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发表时间：
1951
期刊：
影响因子：
--
通讯作者：
J. H. Boyer
中科院分区：
文献类型：
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作者：
P. Smith;J. H. Boyer
由私人助理。S. Smith和J. H.以苯胺为原料，经重氮化和与叠氮化钠偶联制得邻（α-吡啶基）和邻（O-吡啶基）叠氮苯。前者在“惰性”溶剂中加热时转化为邻-α-吡啶基;-苯胺（XII），而后者以良好的产率环化成α-和-咔啉（VIII，IX）的混合物。邻硝基苯胺经重氮化后与噻吩偶联，再经还原制得邻（α-噻吩基）苯胺。然后将产物转化为相应的叠氮化物，叠氮化物以良好的产率环化成4-噻吩并[3，2-B]吲哚（VI）。由于邻叠氮基联苯（I）和某些取代的衍生物的热分解证明了咔唑（II）和相应衍生物的方便合成，因此进行了该反应在合成与咔唑等排化合物中的应用的研究。本文报道了邻-（α-噻吩基）-叠氮苯和邻-（α-吡啶基）-叠氮苯及其顺式异构体的研究。
By P. A. S. Smith and J. H. Boyer o-(a-Pyridyl) and o-(0-pyridyl)-phenyl azide have been prepared from the corresponding anilines bydiazotization and coupling with sodium azide. The former is converted to o-i'a-pyridyl;-aniline (XII) when heated in “inert” solvents, but the latter cyclizesto a mixture of a- and-carboline (VIII, IX) in good yield. o-(a-Thienyl)-aniline was prepared by coupling diazotized o-nitroaniline with thiophene followed by reduction. The product was then converted to the corresponding azide, which was cyclized in good yield to 4-thieno [3, 2-b] indole (VI).Since the thermal decomposition of o-azido-biphenyl (I) and certain substituted derivatives proved a convenient synthesis of carbazole (II) and corresponding derivatives, 111 an investigation of the application of the reaction for the synthesis of compounds isosteric with carbazole was undertaken. The investigation of o-(-thienyl)-phenyl azide and o-(a-pyridyl)-phenyl azide and its ß-isomer are reported here.