Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes
Abstract An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of E and Z ) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthes...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2016-11, Vol.48 (22), p.3996-4008 |
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| container_title | Synthesis (Stuttgart) |
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| creator | Kadam, Kishorkumar S. Gandhi, Thirumanavelan Gupte, Amol Gangopadhyay, A. K. Sharma, Rajiv |
| description | Abstract
An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of
E
and
Z
) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either
tert
-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent
in situ
[3+2] dipolar cycloaddition to the substituted alkynes to give 3,5-disubstituted isoxazoles regioselectively in high to excellent yields. The developed synthetic methodology was applied for the synthesis of a previously reported potent hDGAT1 inhibitor. |
| doi_str_mv | 10.1055/s-0035-1561464 |
| format | Article |
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An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of
E
and
Z
) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either
tert
-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent
in situ
[3+2] dipolar cycloaddition to the substituted alkynes to give 3,5-disubstituted isoxazoles regioselectively in high to excellent yields. The developed synthetic methodology was applied for the synthesis of a previously reported potent hDGAT1 inhibitor.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0035-1561464</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2016-11, Vol.48 (22), p.3996-4008</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c343t-8f0c669a3f5214653b1c6f7cc68d44b8417a37e77fedaf8ba5b63d4974065e2a3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0035-1561464.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0035-1561464$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Kadam, Kishorkumar S.</creatorcontrib><creatorcontrib>Gandhi, Thirumanavelan</creatorcontrib><creatorcontrib>Gupte, Amol</creatorcontrib><creatorcontrib>Gangopadhyay, A. K.</creatorcontrib><creatorcontrib>Sharma, Rajiv</creatorcontrib><title>Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of
E
and
Z
) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either
tert
-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent
in situ
[3+2] dipolar cycloaddition to the substituted alkynes to give 3,5-disubstituted isoxazoles regioselectively in high to excellent yields. The developed synthetic methodology was applied for the synthesis of a previously reported potent hDGAT1 inhibitor.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp1kMlOwzAQQC0EEqVw5ewPwGDHW8KtKlulqkUsErfIScbUJY2R7aKWrydVe-U0Gs28WR5Cl4xeMyrlTSSUckmYVEwocYQGTHBNMkY_jtGgLxVE5zk7RWcxLimlOuPFAPlR-7Vt8cyl4BLEWzzzP9DiFzCf0KWIrQ943gF59gm_bru0gOgi9hbzK0nuXFxXMbm0TtDgSfQb8-tb6KngV3jUNn7jVn1qugbv9nQQz9GJNW2Ei0McoveH-7fxE5nOHyfj0ZTUXPBEcktrpQrDrcz6bySvWK2srmuVN0JUuWDacA1aW2iMzSsjK8UbUWhBlYTM8CG63s-tg48xgC2_g1uZsC0ZLXe6yljudJUHXT1A9kBaOFhBufTr0PUX_tf_B_zbbHI</recordid><startdate>20161116</startdate><enddate>20161116</enddate><creator>Kadam, Kishorkumar S.</creator><creator>Gandhi, Thirumanavelan</creator><creator>Gupte, Amol</creator><creator>Gangopadhyay, A. K.</creator><creator>Sharma, Rajiv</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20161116</creationdate><title>Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes</title><author>Kadam, Kishorkumar S. ; Gandhi, Thirumanavelan ; Gupte, Amol ; Gangopadhyay, A. K. ; Sharma, Rajiv</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c343t-8f0c669a3f5214653b1c6f7cc68d44b8417a37e77fedaf8ba5b63d4974065e2a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kadam, Kishorkumar S.</creatorcontrib><creatorcontrib>Gandhi, Thirumanavelan</creatorcontrib><creatorcontrib>Gupte, Amol</creatorcontrib><creatorcontrib>Gangopadhyay, A. K.</creatorcontrib><creatorcontrib>Sharma, Rajiv</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kadam, Kishorkumar S.</au><au>Gandhi, Thirumanavelan</au><au>Gupte, Amol</au><au>Gangopadhyay, A. K.</au><au>Sharma, Rajiv</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2016-11-16</date><risdate>2016</risdate><volume>48</volume><issue>22</issue><spage>3996</spage><epage>4008</epage><pages>3996-4008</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of
E
and
Z
) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either
tert
-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent
in situ
[3+2] dipolar cycloaddition to the substituted alkynes to give 3,5-disubstituted isoxazoles regioselectively in high to excellent yields. The developed synthetic methodology was applied for the synthesis of a previously reported potent hDGAT1 inhibitor.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0035-1561464</doi><tpages>13</tpages></addata></record> |
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| language | eng |
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| source | Thieme Connect Journals |
| title | Alkyl Nitrites: Novel Reagents for One-Pot Synthesis of 3,5-Disubstituted Isoxazoles from Aldoximes and Alkynes |
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