Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines
Ketonitrones containing two ester groups react regio- and stereoselectively with 1,3-diarylpropenones to form isoxazolidines with ester groups at position 3 of the ring. The action of zinc in acetic acid on these isoxazolidines causes opening of the ring with the formation of 3-amino alcohols, the s...
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| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-09, Vol.56 (9), p.1193-1201 |
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| container_end_page | 1201 |
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| container_issue | 9 |
| container_start_page | 1193 |
| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 56 |
| creator | Sirotkina, Ekaterina V. Efremova, Mariia M. Starova, Galina L. Kuznetsov, Mikhail A. Molchanov, Alexander P. |
| description | Ketonitrones containing two ester groups react regio- and stereoselectively with 1,3-diarylpropenones to form isoxazolidines with ester groups at position 3 of the ring. The action of zinc in acetic acid on these isoxazolidines causes opening of the ring with the formation of 3-amino alcohols, the subsequent cyclization of which leads to polysubstituted lactones. Reduction of the benzoyl group of isoxazolidine with sodium borohydride leads, as a result of subsequent transformations, to the formation of substituted 1,3,4-triaryl-6-oxodihydro-1
H
,3
H
-furo[3,4-
c
]isoxazole-6a(6
H
)-carboxylates as single diastereomers. |
| doi_str_mv | 10.1007/s10593-020-02797-z |
| format | Article |
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H
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H
,3
H
-furo[3,4-
c
]isoxazole-6a(6
H
)-carboxylates as single diastereomers.</description><subject>Acetic acid</subject><subject>Alcohols</subject><subject>Carboxylates</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Cycloaddition</subject><subject>Heterocyclic compounds</subject><subject>Isoxazolidines</subject><subject>Lactones</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9UV1LBCEUlSho-_gDPQ302pTOdUbnMZa-IOilnsUddXOZ1U1dqP313W2C3kJEvJxzPMdDyAWj14xScZMZbXuoaUNxi17UuwMyY62AWkILh2RGKe1rYE1zTE5yXuFVMMlnZDP_GsaojfHFx1BFVwVfUgw2VyVW7Apq43X6Gjcpbmz4metgqrxdZPuxtaFUJemQXUxrvVfIe4nybqtk83YsPiwrn-On3sXRG4_0M3Lk9Jjt-e95St7u717nj_Xzy8PT_Pa5HqCVpbaa867vtBYYohk6J3nXdcAdt5pqBlpI6KUEITphQJpWyAUfJAK5dsIaOCWXky46R6O5qFXcpoBPqoYLEFL0rEXU9YRa6tEqH1zEOAMuY9d-wLjO4_y24wwYSCaQ0EyEIcWck3Vqk_waf0gxqvZVqKkKhVWonyrUDkkwkTKCw9KmPy__sL4BtrCOiQ</recordid><startdate>20200901</startdate><enddate>20200901</enddate><creator>Sirotkina, Ekaterina V.</creator><creator>Efremova, Mariia M.</creator><creator>Starova, Galina L.</creator><creator>Kuznetsov, Mikhail A.</creator><creator>Molchanov, Alexander P.</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20200901</creationdate><title>Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines</title><author>Sirotkina, Ekaterina V. ; Efremova, Mariia M. ; Starova, Galina L. ; Kuznetsov, Mikhail A. ; Molchanov, Alexander P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c358t-ea44696aa75732c6f8466634f4ea0a13a78398837767d38d578b4c8c6f4af7ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Acetic acid</topic><topic>Alcohols</topic><topic>Carboxylates</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Cycloaddition</topic><topic>Heterocyclic compounds</topic><topic>Isoxazolidines</topic><topic>Lactones</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sirotkina, Ekaterina V.</creatorcontrib><creatorcontrib>Efremova, Mariia M.</creatorcontrib><creatorcontrib>Starova, Galina L.</creatorcontrib><creatorcontrib>Kuznetsov, Mikhail A.</creatorcontrib><creatorcontrib>Molchanov, Alexander P.</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sirotkina, Ekaterina V.</au><au>Efremova, Mariia M.</au><au>Starova, Galina L.</au><au>Kuznetsov, Mikhail A.</au><au>Molchanov, Alexander P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2020-09-01</date><risdate>2020</risdate><volume>56</volume><issue>9</issue><spage>1193</spage><epage>1201</epage><pages>1193-1201</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>Ketonitrones containing two ester groups react regio- and stereoselectively with 1,3-diarylpropenones to form isoxazolidines with ester groups at position 3 of the ring. The action of zinc in acetic acid on these isoxazolidines causes opening of the ring with the formation of 3-amino alcohols, the subsequent cyclization of which leads to polysubstituted lactones. Reduction of the benzoyl group of isoxazolidine with sodium borohydride leads, as a result of subsequent transformations, to the formation of substituted 1,3,4-triaryl-6-oxodihydro-1
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| identifier | ISSN: 0009-3122 |
| ispartof | Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2020-09, Vol.56 (9), p.1193-1201 |
| issn | 0009-3122 1573-8353 |
| language | eng |
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| source | SpringerNature Journals |
| subjects | Acetic acid Alcohols Carboxylates Chemistry Chemistry and Materials Science Cycloaddition Heterocyclic compounds Isoxazolidines Lactones Organic Chemistry Pharmacy |
| title | Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines |
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