Abstract

An efficient protocol for the synthesis of polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine-3,4b,5,6,7(1H)-pentacarboxylates was developed by a three-component reaction. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine-3,4b,5,6,7(1H)-pentacarboxylates in high yields and with high diastereoselectivity. The reaction was finished by in situ generation of activated 5-(alkylimino)cyclopenta-1,3-dienes from addition of alkyl isocyanide to two molecules of but-2-ynedioates and sequential formal [3 + 2] cycloaddition reaction with 5,6-unsubstituted 1,4-dihydropyridine.

Beilstein J. Org. Chem. 2024, 20, 1436–1443. doi:10.3762/bjoc.20.126

 抽象的

通过三组分反应开发了一种有效合成多官能化四氢环戊[4,5]吡咯并[2,3- b ]吡啶-3,4b,5,6,7(1 H )-五甲酸酯的方案。在不存在任何催化剂的情况下，烷基异氰化物、二烷基丁-2-炔二酸酯和5,6-未取代的1,4-二氢吡啶在回流乙腈中发生三组分反应，得到多官能化四氢环戊[4,5]吡咯并[2,3- b ]吡啶-3,4b,5,6,7(1 H )-五甲酸酯，产率高，非对映选择性高。该反应通过将烷基异氰化物加成到两分子丁-2-炔二酸酯上原位生成活化的5-(烷基亚氨基)环戊-1,3-二烯，并与5,6进行连续的正式[3 + 2]环加成反应来完成-未取代的1,4-二氢吡啶。

Beilstein J. Org. Chem. 2024, 20, 1436–1443. doi:10.3762/bjoc.20.126