Highly Diastereoselective Synthesis of Polycyclic Indolines through Formal [4+2] Propargylic Cycloaddition of Indoles with Ethynyl Benzoxazinanones
A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of tetrahydro‐5H‐indolo[2,3‐b]quinolines and tetrahydro‐3H‐pyrrolo[3,2‐b]quinoline, the core structures of alkaloid frameworks, featuring excellent yie...
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| Published in | Chemistry, an Asian journal Vol. 15; no. 16; pp. 2462 - 2466 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
Wiley Subscription Services, Inc
17.08.2020
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| Abstract | A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of tetrahydro‐5H‐indolo[2,3‐b]quinolines and tetrahydro‐3H‐pyrrolo[3,2‐b]quinoline, the core structures of alkaloid frameworks, featuring excellent yields, high diastereoselectivity, mild conditions and wide substrate scope.
A metal‐free formal [4+2] propargylic cycloaddition between aza‐oQMs, which is in situ generated from ethynyl benzoxazinanones assisted by a common Brønsted base, and simple indole derivatives has been developed. This method provides a convenient and practical access to a variety of single diastereoisomeric polycyclic indolines in excellent yields under open‐flask ambient conditions. |
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| AbstractList | A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of tetrahydro‐5H‐indolo[2,3‐b]quinolines and tetrahydro‐3H‐pyrrolo[3,2‐b]quinoline, the core structures of alkaloid frameworks, featuring excellent yields, high diastereoselectivity, mild conditions and wide substrate scope.
A metal‐free formal [4+2] propargylic cycloaddition between aza‐oQMs, which is in situ generated from ethynyl benzoxazinanones assisted by a common Brønsted base, and simple indole derivatives has been developed. This method provides a convenient and practical access to a variety of single diastereoisomeric polycyclic indolines in excellent yields under open‐flask ambient conditions. A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of tetrahydro‐5H‐indolo[2,3‐b]quinolines and tetrahydro‐3H‐pyrrolo[3,2‐b]quinoline, the core structures of alkaloid frameworks, featuring excellent yields, high diastereoselectivity, mild conditions and wide substrate scope. A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of tetrahydro‐5 H ‐indolo[2,3‐ b ]quinolines and tetrahydro‐3 H ‐pyrrolo[3,2‐ b ]quinoline, the core structures of alkaloid frameworks, featuring excellent yields, high diastereoselectivity, mild conditions and wide substrate scope. |
| Author | Shao, Wen You, Shu‐Li Xu‐Xu, Qing‐Feng |
| Author_xml | – sequence: 1 givenname: Wen surname: Shao fullname: Shao, Wen organization: University of Chinese Academy of Sciences – sequence: 2 givenname: Qing‐Feng surname: Xu‐Xu fullname: Xu‐Xu, Qing‐Feng organization: University of Chinese Academy of Sciences – sequence: 3 givenname: Shu‐Li orcidid: 0000-0003-4586-8359 surname: You fullname: You, Shu‐Li email: slyou@sioc.ac.cn organization: University of Chinese Academy of Sciences |
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| Snippet | A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of... |
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| SubjectTerms | Chemical reactions Chemistry Cycloaddition Heterocyclic compounds Indoles indoline Organic compounds propargylation pyrrole Quinoline quinone methide Stereoselectivity Substrates Synthesis |
| Title | Highly Diastereoselective Synthesis of Polycyclic Indolines through Formal [4+2] Propargylic Cycloaddition of Indoles with Ethynyl Benzoxazinanones |
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