Chemistry Department, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
J Org Chem. 2013 Dec 6;78(23):11860-73. doi: 10.1021/jo401892t. Epub 2013 Nov 26.
A general method is described for the synthesis of 1,3'-bipyrroles. The route involves constructing a pyrrole ring on the nitrogen of a substituted 1H-pyrrole, so as to generate the 1,3'-bipyrrole. In this approach the nitrogen of the starting pyrrole was alkylated with a special Michael acceptor having an allylic leaving group, and the product was then modified in such a way that the second pyrrole ring could be formed by a Paal-Knorr reaction. Two variants of this sequence were examined, one of which led to formation of a 3-hydroxypyridine instead of the second pyrrole ring; the other variant used phenacyl bromide instead of the special Michael acceptor.
描述了一种合成 1,3'-联吡啶的一般方法。该路线涉及在取代的 1H-吡咯的氮上构建吡咯环，从而生成 1,3'-联吡啶。在这种方法中，起始吡咯的氮用具有烯丙基离去基团的特殊迈克尔受体烷基化，然后对产物进行修饰，以便通过 Paal-Knorr 反应形成第二个吡咯环。该序列有两种变体，其中一种导致形成 3-羟基吡啶而不是第二个吡咯环；另一种变体使用苯乙酮溴而不是特殊的迈克尔受体。
