SYNTHESIS OF ALKYLPYRROLES BY THE SODIUM-BOROHYDRIDE REDUCTION OF ACYLPYRROLES
SYNTHESIS OF ALKYLPYRROLES BY THE SODIUM-BOROHYDRIDE REDUCTION OF ACYLPYRROLES
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DOI：
10.1021/jo00216a030
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发表时间：
1985-01-01
影响因子：
3.6
通讯作者：
MUCHOWSKI, JM
中科院分区：
文献类型：
--
作者：
GREENHOUSE, R;RAMIREZ, C;MUCHOWSKI, JM
用硼氢化钠在沸腾的2-丙醇中还原相应的酰基吡咯，得到n -未取代的烷基丙罗。该反应通过吡咯烷基醇进行，并由叔醇24扩展为支链烷基吡咯25。烷基吡咯的制备方法有很多种，其中对易于获得的c -酰基吡咯的还原尤为重要。这种还原是通过Wolff-Kishner方法、氢化铝锂、二硼烷和催化加氢完成的。2此外，用硼氢化钠在煮沸的二氧氧烷中还原2-苯甲酰吡咯，用锂在氨水中还原4 - 2，或用硼氢化锂或氰硼氢化钠还原6-芳基-6-（IV， IV -二烷基胺）-1-氮杂鎓盐，合成了多种2-苄基吡咯。在上面提到的还原方法中，Wolff-Kishner法和氢化铝锂法是最有用的，但其剧烈的性质和/或缺乏选择性减少了它们的应用范围。
N-Unsubstituted alkylprroles are obtained by the reduction of the corresponding acylpyrroles with sodium borohydride in boiling 2-propanol. This reaction was demonstrated to proceed via the pyrrolylalkylcarbinol and was extended to the synthesis of a branched chain alkylpyrrole 25 from the tertiary alcohol 24.Alkylpyrroles can be prepared by a variety of methods, among which thereduction of the very readily available C-acylpyrroles is of particular importance. This reduction has been accomplishedby the Wolff-Kishner method, with lithium aluminum hydride, with diborane, and by catalytic hydrogenation. 2 In addition, diverse 2-benzylpyrroles have been synthesized by the reduction of 2-benzoylpyrroles with sodium borohydride in boiling dioxane3 and with lithium in ammonia4 or by the lithium borohydride or sodium cyanoborohydride reduction of 6-aryl-6-(IV, iV-di-alkylamino)-1-azafulvinium salts. 5 Of the reductive methods cited above, the Wolff-Kishner and lithium alu-minum hydride processes are the most useful, but the vigorous nature and/or lack of selectivity thereof decreases their scope.