A diversity-oriented synthesis of cyclopenta[b]pyrroles and related compounds through a calcium(II)/copper(II) catalytic sequence,Organic Chemistry Frontiers

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A diversity-oriented synthesis of cyclopenta[b]pyrroles and related compounds through a calcium(II)/copper(II) catalytic sequence
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-11-14 00:00:00 , DOI: 10.1039/c7qo00948h
L. Marin _{1,

2,

3,

4,

5} , R. Guillot _{1,

2,

3,

4,

5} , V. Gandon _{1,

2,

3,

4,

5} , E. Schulz _{1,

2,

3,

4,

5} , D. Lebœuf _{1,

2,

3,

4,

5}

Affiliation

We report herein a sequential bicatalytic route to provide a versatile access to a wide range of synthetically useful nitrogen-containing heterocycles in a single pot from furan and aniline derivatives. This transformation relies on an aza-Piancatelli/hydroamination sequence promoted by common calcium(II) and copper(II) salts. Depending on the substitution pattern of the precursors as well as the solvent employed, this method enables the preparation of biologically relevant molecules such as cyclopenta[b]pyrroles, pyrrolo[1,2-a]quinoxalines and also a novel class of cyclopenta[b]pyrrolines. Moreover, the first atropodiastereoselective synthesis of N-aryl cyclopenta[b]pyrroles is described.

中文翻译：

通过钙（II）/铜（II）催化序列的多元取向合成环戊[ b ]吡咯和相关化合物

我们在本文中报道了一种顺序双催化路线，以从呋喃和苯胺衍生物的单一反应罐中提供广泛的合成可用的含氮杂环的通用途径。这种转化依赖于常见的钙盐（II）和铜盐（II）促进的aza-Piancatelli /加氢胺化序列。根据前体的取代方式以及所用溶剂的不同，该方法能够制备生物学上相关的分子，例如环戊[ b ]吡咯，吡咯并[1,2- a ]喹喔啉以及一类新型的环戊[ b]。 ]吡咯啉。此外，N-芳基环戊五烯的第一对映体非对映选择性合成[ b描述了]吡咯。

更新日期：2017-11-20

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