通过金催化末端炔烃键合的吡咯的氢芳基化反应来获得吡咯并吡啶。
Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes.
机构信息
Dipartimento di Scienze Chimiche e Ambientali Università dell'Insubria, Via Valleggio 11, 22100 Como, Italy.
出版信息
Beilstein J Org Chem. 2011;7:1468-74. doi: 10.3762/bjoc.7.170. Epub 2011 Oct 26.
Abstract
In a simple procedure, the intramolecular hydroarylation of N-propargyl-pyrrole-2-carboxamides was accomplished with the aid of gold(III) catalysis. The reaction led to differently substituted pyrrolo[2,3-c]pyridine and pyrrolo[3,2-c]pyridine derivatives arising either from direct cyclization or from a formal rearrangement of the carboxamide group. Terminal alkynes are essential to achieve bicyclic pyrrolo-fused pyridinones by a 6-exo-dig process, while the presence of a phenyl group at the C-C triple bond promotes the 7-endo-dig cyclization giving pyrrolo-azepines.
摘要
在一个简单的步骤中，通过金（III）催化实现了 N-炔丙基-吡咯-2-甲酰胺的分子内氢芳基化反应。该反应导致了不同取代的吡咯并[2,3-c]吡啶和吡咯并[3,2-c]吡啶衍生物的产生，这些产物要么来自直接环化，要么来自酰胺基团的形式重排。末端炔烃是通过 6-endo-dig 过程形成双环吡咯并稠合吡啶酮的必要条件，而在 C-C 三键上存在苯基基团则促进了 7-endo-dig 环化，生成吡咯并氮杂环庚烷。
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