Additive-free synthesis of fused tricyclic cyanoisoxazolidines using formed cyanonitrones
Herein, we disclose the first report on the generation of cyanonitrone in situ from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access fused tricyclic cyanoisoxazolidines. Further, this methodology could be extended to access fused tricyclic...
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| Published in | Chemical communications (Cambridge, England) Vol. 59; no. 4; pp. 446 - 449 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Published |
05.01.2023
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| Online Access | Get full text |
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| Abstract | Herein, we disclose the first report on the generation of cyanonitrone
in situ
from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access fused tricyclic cyanoisoxazolidines. Further, this methodology could be extended to access fused tricyclic trifluoromethylated and phosphonylated isoxazolidines. Surprisingly, the reductive ring-opening of cyanoisoxazolidines was followed by a spontaneous lactonization to produce fused tricyclic amino lactones. Moreover, the N-O bond of the obtained tricyclic trifluoromethylated isoxazolidines could be cleaved to obtain 1,3-amino alcohols.
Herein, we disclose the generation of cyanonitrone from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access an important class of fused tricyclic cyanoisoxazolidines. |
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| AbstractList | Herein, we disclose the first report on the generation of cyanonitrone
in situ
from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access fused tricyclic cyanoisoxazolidines. Further, this methodology could be extended to access fused tricyclic trifluoromethylated and phosphonylated isoxazolidines. Surprisingly, the reductive ring-opening of cyanoisoxazolidines was followed by a spontaneous lactonization to produce fused tricyclic amino lactones. Moreover, the N-O bond of the obtained tricyclic trifluoromethylated isoxazolidines could be cleaved to obtain 1,3-amino alcohols.
Herein, we disclose the generation of cyanonitrone from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to access an important class of fused tricyclic cyanoisoxazolidines. |
| Author | Babu, Mary Merlin Manjaly Jamali, Muhammad Fahad Mohanan, Kishor Kant, Ruchir Yadav, Usha |
| AuthorAffiliation | CSIR-Central Drug Research Institute Medicinal and Process Chemistry Division Academy of Scientific and Innovative Research (AcSIR) Molecular and Structural Biology Division |
| AuthorAffiliation_xml | – name: CSIR-Central Drug Research Institute – name: Medicinal and Process Chemistry Division – name: Molecular and Structural Biology Division – name: Academy of Scientific and Innovative Research (AcSIR) |
| Author_xml | – sequence: 1 givenname: Muhammad Fahad surname: Jamali fullname: Jamali, Muhammad Fahad – sequence: 2 givenname: Usha surname: Yadav fullname: Yadav, Usha – sequence: 3 givenname: Mary Merlin Manjaly surname: Babu fullname: Babu, Mary Merlin Manjaly – sequence: 4 givenname: Ruchir surname: Kant fullname: Kant, Ruchir – sequence: 5 givenname: Kishor surname: Mohanan fullname: Mohanan, Kishor |
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| DOI | 10.1039/d2cc05831f |
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| Notes | For ESI and crystallographic data in CIF or other electronic format see DOI https://doi.org/10.1039/d2cc05831f Electronic supplementary information (ESI) available: Detailed experimental procedures, complete characterization data, CIF for copies of NMR spectra. CCDC 2091413 5a |
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| Snippet | Herein, we disclose the first report on the generation of cyanonitrone
in situ
from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition... |
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| Title | Additive-free synthesis of fused tricyclic cyanoisoxazolidines using formed cyanonitrones |
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