高氯酸锂、乙酸酐和三苯基膦辅助的4-未取代的2,5-二氧代八氢喹啉-3-羧酸酯和3-腈的多组分合成
Lithium Perchlorate-, Acetic Anhydride-, and Triphenylphosphine-assisted Multicomponent Syntheses of 4-Unsubstituted 2,5-Dioxooctahydroquinoline-3-carboxylates and 3-carbonitriles.
作者信息
Gu Xingxian, Georg Gunda I
机构信息
Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66045.
Department of Medicinal Chemistry and Institute for Therapeutics Discovery and Development, University of Minnesota, 717 Delaware Street, SE, Minneapolis, Minnesota 55414, United States.
出版信息
Tetrahedron. 2013 Nov 11;69(45):9406-9416. doi: 10.1016/j.tet.2013.08.081. Epub 2013 Sep 5.
Abstract
Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3-carbonitriles were obtained in a one-flask reaction.
摘要
高氯酸锂和乙酸酐是3-氨基环己-2-烯酮、甲醛和丙二酸酯之间多组分反应的关键添加剂，该反应生成的加合物在酸性条件下环化，得到双环2,5-二氧代八氢喹啉-3-羧酸酯。当氰基乙酸甲酯在催化量的三苯基膦存在下进行相同的反应条件时，在单瓶反应中得到双环2,5-二氧代八氢喹啉-3-腈。
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