Synthesis of Bulky N ‐Acyl Heterocycles by DMAPO/Boc 2 O‐Mediated One‐Pot Direct N ‐Acylation of Less Nucleophilic N ‐Heterocycles with α‐Fully Substituted Carboxylic Acids
This report describes a general method for the one‐pot direct N ‐acylation of N ‐heterocycles using our previously developed 4‐( N , N ‐dimethylamino)pyridine N ‐oxide (DMAPO)/di‐ tert ‐butyl dicarbonate (Boc 2 O) system. This system enables one‐pot N ‐acylation reactions to provide bulky N ‐acyl he...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2023-07, Vol.365 (14), p.2367-2376 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2376 |
|---|---|
| container_issue | 14 |
| container_start_page | 2367 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 365 |
| creator | Umehara, Atsushi Shimizu, Soma Sasaki, Makoto |
| description | This report describes a general method for the one‐pot direct
N
‐acylation of
N
‐heterocycles using our previously developed 4‐(
N
,
N
‐dimethylamino)pyridine
N
‐oxide (DMAPO)/di‐
tert
‐butyl dicarbonate (Boc
2
O) system. This system enables one‐pot
N
‐acylation reactions to provide bulky
N
‐acyl heterocycles starting from a wide variety of less nucleophilic
N
‐heterocycles and sterically hindered α‐fully substituted carboxylic acids in high yields. Moreover, this one‐pot method does not involve pre‐activation of substrates. The protocol has been successfully extended to one‐pot
N
‐acylation of 7‐azaindoles. |
| doi_str_mv | 10.1002/adsc.202300487 |
| format | Article |
| fullrecord | <record><control><sourceid>crossref</sourceid><recordid>TN_cdi_crossref_primary_10_1002_adsc_202300487</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1002_adsc_202300487</sourcerecordid><originalsourceid>FETCH-LOGICAL-c847-d1c82cf9418050a466538475055e680192249c38b808e938f0c65d47c76d7f753</originalsourceid><addsrcrecordid>eNpVkE1OwzAQhS0EEqWwZe0LpB0ncews05ZSpP5J7T5KHEc1hLqKHYF3HIGrsOQSHIKTkKioiNXMPL35nvQQuiUwIAD-MCuMGPjgBwAhZ2eoRyJCvZBE8flpp3CJrox5BCCMM9ZDnxu3tztplMG6xKOmenJ4ib_f3hPhKjyTVtZaOFFJg3OHJ4tkvRqOtMA-XrWmhSxUZmWBV3vZnmtt8UTVUtg_RmaV3nfsuTQGL5sWpQ87VSlx9PyLeFF2h78-WnnaVJXDmyY3Vtmmixhnda5fXfeYCFWYa3RRZpWRN7-zj7bTu-145s1X9w_jZO4JHjKvIIL7ooxDwoFCFkYRDVqdAqUy4kBi3w9jEfCcA5dxwEsQES1CJlhUsJLRoI8GR6yotTG1LNNDrZ6z2qUE0q73tOs9PfUe_AAJhn0O</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis of Bulky N ‐Acyl Heterocycles by DMAPO/Boc 2 O‐Mediated One‐Pot Direct N ‐Acylation of Less Nucleophilic N ‐Heterocycles with α‐Fully Substituted Carboxylic Acids</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Umehara, Atsushi ; Shimizu, Soma ; Sasaki, Makoto</creator><creatorcontrib>Umehara, Atsushi ; Shimizu, Soma ; Sasaki, Makoto</creatorcontrib><description>This report describes a general method for the one‐pot direct
N
‐acylation of
N
‐heterocycles using our previously developed 4‐(
N
,
N
‐dimethylamino)pyridine
N
‐oxide (DMAPO)/di‐
tert
‐butyl dicarbonate (Boc
2
O) system. This system enables one‐pot
N
‐acylation reactions to provide bulky
N
‐acyl heterocycles starting from a wide variety of less nucleophilic
N
‐heterocycles and sterically hindered α‐fully substituted carboxylic acids in high yields. Moreover, this one‐pot method does not involve pre‐activation of substrates. The protocol has been successfully extended to one‐pot
N
‐acylation of 7‐azaindoles.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202300487</identifier><language>eng</language><ispartof>Advanced synthesis & catalysis, 2023-07, Vol.365 (14), p.2367-2376</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c847-d1c82cf9418050a466538475055e680192249c38b808e938f0c65d47c76d7f753</citedby><cites>FETCH-LOGICAL-c847-d1c82cf9418050a466538475055e680192249c38b808e938f0c65d47c76d7f753</cites><orcidid>0000-0002-3705-5078</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Umehara, Atsushi</creatorcontrib><creatorcontrib>Shimizu, Soma</creatorcontrib><creatorcontrib>Sasaki, Makoto</creatorcontrib><title>Synthesis of Bulky N ‐Acyl Heterocycles by DMAPO/Boc 2 O‐Mediated One‐Pot Direct N ‐Acylation of Less Nucleophilic N ‐Heterocycles with α‐Fully Substituted Carboxylic Acids</title><title>Advanced synthesis & catalysis</title><description>This report describes a general method for the one‐pot direct
N
‐acylation of
N
‐heterocycles using our previously developed 4‐(
N
,
N
‐dimethylamino)pyridine
N
‐oxide (DMAPO)/di‐
tert
‐butyl dicarbonate (Boc
2
O) system. This system enables one‐pot
N
‐acylation reactions to provide bulky
N
‐acyl heterocycles starting from a wide variety of less nucleophilic
N
‐heterocycles and sterically hindered α‐fully substituted carboxylic acids in high yields. Moreover, this one‐pot method does not involve pre‐activation of substrates. The protocol has been successfully extended to one‐pot
N
‐acylation of 7‐azaindoles.</description><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpVkE1OwzAQhS0EEqWwZe0LpB0ncews05ZSpP5J7T5KHEc1hLqKHYF3HIGrsOQSHIKTkKioiNXMPL35nvQQuiUwIAD-MCuMGPjgBwAhZ2eoRyJCvZBE8flpp3CJrox5BCCMM9ZDnxu3tztplMG6xKOmenJ4ib_f3hPhKjyTVtZaOFFJg3OHJ4tkvRqOtMA-XrWmhSxUZmWBV3vZnmtt8UTVUtg_RmaV3nfsuTQGL5sWpQ87VSlx9PyLeFF2h78-WnnaVJXDmyY3Vtmmixhnda5fXfeYCFWYa3RRZpWRN7-zj7bTu-145s1X9w_jZO4JHjKvIIL7ooxDwoFCFkYRDVqdAqUy4kBi3w9jEfCcA5dxwEsQES1CJlhUsJLRoI8GR6yotTG1LNNDrZ6z2qUE0q73tOs9PfUe_AAJhn0O</recordid><startdate>20230718</startdate><enddate>20230718</enddate><creator>Umehara, Atsushi</creator><creator>Shimizu, Soma</creator><creator>Sasaki, Makoto</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-3705-5078</orcidid></search><sort><creationdate>20230718</creationdate><title>Synthesis of Bulky N ‐Acyl Heterocycles by DMAPO/Boc 2 O‐Mediated One‐Pot Direct N ‐Acylation of Less Nucleophilic N ‐Heterocycles with α‐Fully Substituted Carboxylic Acids</title><author>Umehara, Atsushi ; Shimizu, Soma ; Sasaki, Makoto</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c847-d1c82cf9418050a466538475055e680192249c38b808e938f0c65d47c76d7f753</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Umehara, Atsushi</creatorcontrib><creatorcontrib>Shimizu, Soma</creatorcontrib><creatorcontrib>Sasaki, Makoto</creatorcontrib><collection>CrossRef</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Umehara, Atsushi</au><au>Shimizu, Soma</au><au>Sasaki, Makoto</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Bulky N ‐Acyl Heterocycles by DMAPO/Boc 2 O‐Mediated One‐Pot Direct N ‐Acylation of Less Nucleophilic N ‐Heterocycles with α‐Fully Substituted Carboxylic Acids</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2023-07-18</date><risdate>2023</risdate><volume>365</volume><issue>14</issue><spage>2367</spage><epage>2376</epage><pages>2367-2376</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>This report describes a general method for the one‐pot direct
N
‐acylation of
N
‐heterocycles using our previously developed 4‐(
N
,
N
‐dimethylamino)pyridine
N
‐oxide (DMAPO)/di‐
tert
‐butyl dicarbonate (Boc
2
O) system. This system enables one‐pot
N
‐acylation reactions to provide bulky
N
‐acyl heterocycles starting from a wide variety of less nucleophilic
N
‐heterocycles and sterically hindered α‐fully substituted carboxylic acids in high yields. Moreover, this one‐pot method does not involve pre‐activation of substrates. The protocol has been successfully extended to one‐pot
N
‐acylation of 7‐azaindoles.</abstract><doi>10.1002/adsc.202300487</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-3705-5078</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2023-07, Vol.365 (14), p.2367-2376 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_adsc_202300487 |
| source | Wiley Online Library Journals Frontfile Complete |
| title | Synthesis of Bulky N ‐Acyl Heterocycles by DMAPO/Boc 2 O‐Mediated One‐Pot Direct N ‐Acylation of Less Nucleophilic N ‐Heterocycles with α‐Fully Substituted Carboxylic Acids |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-28T19%3A13%3A06IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Bulky%20N%20%E2%80%90Acyl%20Heterocycles%20by%20DMAPO/Boc%202%20O%E2%80%90Mediated%20One%E2%80%90Pot%20Direct%20N%20%E2%80%90Acylation%20of%20Less%20Nucleophilic%20N%20%E2%80%90Heterocycles%20with%20%CE%B1%E2%80%90Fully%20Substituted%20Carboxylic%20Acids&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Umehara,%20Atsushi&rft.date=2023-07-18&rft.volume=365&rft.issue=14&rft.spage=2367&rft.epage=2376&rft.pages=2367-2376&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.202300487&rft_dat=%3Ccrossref%3E10_1002_adsc_202300487%3C/crossref%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 |