4.4 Article

Synthesis of chromeno[2,3-c]pyrrol-9(2H)-ones by domino Michael-Claisen-SNAr reactions of amino acid esters with 2-chlorophenylpropynones

期刊

TETRAHEDRON
卷 104, 期 -, 页码 -

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132608

关键词

Amino acids; Heterocycles; Domino reactions; Cross-coupling reactions; Palladium

资金

  1. joint research project ONKOTHER-H - European Social Fund (ESF) [ESF/14-BM-A55-0004/18]
  2. Ministry of Education, Science and Culture of Mecklenburg-Vorpommern, Germany
  3. RoHan Project - German Academic Exchange Service (DAAD) [57315854]
  4. Federal Ministry for Economic Cooperation and Development (BMZ)

向作者/读者索取更多资源

The domino reaction of amino acid esters with 2-chlorophenylpropynones, which are readily available through Sonogashira reactions, produces novel chromeno[2,3-c]pyrrol-9(2H)-ones. This multi-step reaction involves Michael, Claisen, and SNAr reactions. Some intermediates were isolated, providing insights into the mechanism.
The domino reaction of amino acid esters with 2-chlorophenylpropynones, readily available by Sonogashira reactions of 2-chlorobenzoylacetylenes, afforded novel chromeno[2,3-c]pyrrol-9(2H)-ones. The domino reaction involves three steps, i.e. Michael, Claisen and SNAr reactions. Intermediates could be isolated in some cases which allowed to get some insight in the mechanism.(c) 2021 Elsevier Ltd. All rights reserved.

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