Direct Synthesis of 5-Acyl-3-oxy-4-pyrones Based On Acid-Catalyzed Acylation of Enaminodiones with Acylbenzotriazoles via Soft Enolization
Abstract A novel convenient acid-catalyzed acylation of enaminodiones with acylbenzotriazoles via soft enolization has been developed for the direct synthesis of hard-to-reach 5-acyl-3-oxy-4-pyrones. The important advantages of the reaction include broad substrate scope, mild conditions, scalability...
Gespeichert in:
| Veröffentlicht in: | Synthesis (Stuttgart) 2020-08, Vol.52 (15), p.2267-2276 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2276 |
|---|---|
| container_issue | 15 |
| container_start_page | 2267 |
| container_title | Synthesis (Stuttgart) |
| container_volume | 52 |
| creator | Obydennov, Dmitrii L. Viktorova, Viktoria V. Chernyshova, Elena V. Shirinkin, Alexander S. Usachev, Sergey A. Sosnovskikh, Vyacheslav Y. |
| description | Abstract
A novel convenient acid-catalyzed acylation of enaminodiones with acylbenzotriazoles via soft enolization has been developed for the direct synthesis of hard-to-reach 5-acyl-3-oxy-4-pyrones. The important advantages of the reaction include broad substrate scope, mild conditions, scalability, and readily isolation of products by crystallization without the use of chromatography. Further modification of the pyrone ring and synthesis of various azaheterocycles via ring-opening transformation have been demonstrated for the preparation of potential scaffolds for inhibition of metalloenzymes. |
| doi_str_mv | 10.1055/s-0040-1707471 |
| format | Article |
| fullrecord | <record><control><sourceid>thieme_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1055_s_0040_1707471</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1055_s_0040_1707471</sourcerecordid><originalsourceid>FETCH-LOGICAL-c277t-aea9ba114cd7d53bd020939ec72b5438042d189ef0c38588fc36931625f8c5ab3</originalsourceid><addsrcrecordid>eNp1kEtOwzAQhi0EEqWwZZ0LuIzjuHaWpZSHVKmLgsQuchxHdZXalW0eyRm4CpfgZCQtW1Yj_fN9o9GP0DWBCQHGbgIGyAATDjzj5ASNSEY5Tgm8nqIRAM0xF4Kco4sQtgDAU5qP0Ned8VrFZN3auNHBhMTVCcMz1TaYYvfZ4gzvW--sDsmtDLpKVjaZKVPhn--5jLJpuz4bcBmNs4O9sHJnrKvMQfowcXPYl9p2LnojO9f0-buRydrVscddY7qDfYnOatkEffU3x-jlfvE8f8TL1cPTfLbEKuU8YqllXkpCMlXxitGyghRymmvF05JlVECWVkTkugZFBROiVnSaUzJNWS0UkyUdo8nxrvIuBK_rYu_NTvq2IFAMXRahGLos_rrsBXwU4sbonS627s3b_sP_-F9zBHeb</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Direct Synthesis of 5-Acyl-3-oxy-4-pyrones Based On Acid-Catalyzed Acylation of Enaminodiones with Acylbenzotriazoles via Soft Enolization</title><source>Thieme Connect Journals</source><creator>Obydennov, Dmitrii L. ; Viktorova, Viktoria V. ; Chernyshova, Elena V. ; Shirinkin, Alexander S. ; Usachev, Sergey A. ; Sosnovskikh, Vyacheslav Y.</creator><creatorcontrib>Obydennov, Dmitrii L. ; Viktorova, Viktoria V. ; Chernyshova, Elena V. ; Shirinkin, Alexander S. ; Usachev, Sergey A. ; Sosnovskikh, Vyacheslav Y.</creatorcontrib><description>Abstract
A novel convenient acid-catalyzed acylation of enaminodiones with acylbenzotriazoles via soft enolization has been developed for the direct synthesis of hard-to-reach 5-acyl-3-oxy-4-pyrones. The important advantages of the reaction include broad substrate scope, mild conditions, scalability, and readily isolation of products by crystallization without the use of chromatography. Further modification of the pyrone ring and synthesis of various azaheterocycles via ring-opening transformation have been demonstrated for the preparation of potential scaffolds for inhibition of metalloenzymes.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0040-1707471</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2020-08, Vol.52 (15), p.2267-2276</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c277t-aea9ba114cd7d53bd020939ec72b5438042d189ef0c38588fc36931625f8c5ab3</citedby><orcidid>0000-0002-6659-9832</orcidid></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-0040-1707471.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0040-1707471$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,777,781,3004,3005,27905,27906,54540,54541</link.rule.ids></links><search><creatorcontrib>Obydennov, Dmitrii L.</creatorcontrib><creatorcontrib>Viktorova, Viktoria V.</creatorcontrib><creatorcontrib>Chernyshova, Elena V.</creatorcontrib><creatorcontrib>Shirinkin, Alexander S.</creatorcontrib><creatorcontrib>Usachev, Sergey A.</creatorcontrib><creatorcontrib>Sosnovskikh, Vyacheslav Y.</creatorcontrib><title>Direct Synthesis of 5-Acyl-3-oxy-4-pyrones Based On Acid-Catalyzed Acylation of Enaminodiones with Acylbenzotriazoles via Soft Enolization</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
A novel convenient acid-catalyzed acylation of enaminodiones with acylbenzotriazoles via soft enolization has been developed for the direct synthesis of hard-to-reach 5-acyl-3-oxy-4-pyrones. The important advantages of the reaction include broad substrate scope, mild conditions, scalability, and readily isolation of products by crystallization without the use of chromatography. Further modification of the pyrone ring and synthesis of various azaheterocycles via ring-opening transformation have been demonstrated for the preparation of potential scaffolds for inhibition of metalloenzymes.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kEtOwzAQhi0EEqWwZZ0LuIzjuHaWpZSHVKmLgsQuchxHdZXalW0eyRm4CpfgZCQtW1Yj_fN9o9GP0DWBCQHGbgIGyAATDjzj5ASNSEY5Tgm8nqIRAM0xF4Kco4sQtgDAU5qP0Ned8VrFZN3auNHBhMTVCcMz1TaYYvfZ4gzvW--sDsmtDLpKVjaZKVPhn--5jLJpuz4bcBmNs4O9sHJnrKvMQfowcXPYl9p2LnojO9f0-buRydrVscddY7qDfYnOatkEffU3x-jlfvE8f8TL1cPTfLbEKuU8YqllXkpCMlXxitGyghRymmvF05JlVECWVkTkugZFBROiVnSaUzJNWS0UkyUdo8nxrvIuBK_rYu_NTvq2IFAMXRahGLos_rrsBXwU4sbonS627s3b_sP_-F9zBHeb</recordid><startdate>20200804</startdate><enddate>20200804</enddate><creator>Obydennov, Dmitrii L.</creator><creator>Viktorova, Viktoria V.</creator><creator>Chernyshova, Elena V.</creator><creator>Shirinkin, Alexander S.</creator><creator>Usachev, Sergey A.</creator><creator>Sosnovskikh, Vyacheslav Y.</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-6659-9832</orcidid></search><sort><creationdate>20200804</creationdate><title>Direct Synthesis of 5-Acyl-3-oxy-4-pyrones Based On Acid-Catalyzed Acylation of Enaminodiones with Acylbenzotriazoles via Soft Enolization</title><author>Obydennov, Dmitrii L. ; Viktorova, Viktoria V. ; Chernyshova, Elena V. ; Shirinkin, Alexander S. ; Usachev, Sergey A. ; Sosnovskikh, Vyacheslav Y.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c277t-aea9ba114cd7d53bd020939ec72b5438042d189ef0c38588fc36931625f8c5ab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Obydennov, Dmitrii L.</creatorcontrib><creatorcontrib>Viktorova, Viktoria V.</creatorcontrib><creatorcontrib>Chernyshova, Elena V.</creatorcontrib><creatorcontrib>Shirinkin, Alexander S.</creatorcontrib><creatorcontrib>Usachev, Sergey A.</creatorcontrib><creatorcontrib>Sosnovskikh, Vyacheslav Y.</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Obydennov, Dmitrii L.</au><au>Viktorova, Viktoria V.</au><au>Chernyshova, Elena V.</au><au>Shirinkin, Alexander S.</au><au>Usachev, Sergey A.</au><au>Sosnovskikh, Vyacheslav Y.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct Synthesis of 5-Acyl-3-oxy-4-pyrones Based On Acid-Catalyzed Acylation of Enaminodiones with Acylbenzotriazoles via Soft Enolization</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2020-08-04</date><risdate>2020</risdate><volume>52</volume><issue>15</issue><spage>2267</spage><epage>2276</epage><pages>2267-2276</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
A novel convenient acid-catalyzed acylation of enaminodiones with acylbenzotriazoles via soft enolization has been developed for the direct synthesis of hard-to-reach 5-acyl-3-oxy-4-pyrones. The important advantages of the reaction include broad substrate scope, mild conditions, scalability, and readily isolation of products by crystallization without the use of chromatography. Further modification of the pyrone ring and synthesis of various azaheterocycles via ring-opening transformation have been demonstrated for the preparation of potential scaffolds for inhibition of metalloenzymes.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0040-1707471</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-6659-9832</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0039-7881 |
| ispartof | Synthesis (Stuttgart), 2020-08, Vol.52 (15), p.2267-2276 |
| issn | 0039-7881 1437-210X |
| language | eng |
| recordid | cdi_crossref_primary_10_1055_s_0040_1707471 |
| source | Thieme Connect Journals |
| title | Direct Synthesis of 5-Acyl-3-oxy-4-pyrones Based On Acid-Catalyzed Acylation of Enaminodiones with Acylbenzotriazoles via Soft Enolization |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-18T09%3A10%3A50IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-thieme_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Direct%20Synthesis%20of%205-Acyl-3-oxy-4-pyrones%20Based%20On%20Acid-%C2%ADCatalyzed%20Acylation%20of%20Enaminodiones%20with%20Acylbenzotriazoles%20via%20Soft%20Enolization&rft.jtitle=Synthesis%20(Stuttgart)&rft.au=Obydennov,%20Dmitrii%20L.&rft.date=2020-08-04&rft.volume=52&rft.issue=15&rft.spage=2267&rft.epage=2276&rft.pages=2267-2276&rft.issn=0039-7881&rft.eissn=1437-210X&rft_id=info:doi/10.1055/s-0040-1707471&rft_dat=%3Cthieme_cross%3E10_1055_s_0040_1707471%3C/thieme_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |