Microwave-Assisted aza-Friedel–Crafts Arylation of N‑Acyliminium Ions: Expedient Access to 4‑Aryl 3,4-Dihydroquinazolinones

A one-pot microwave-assisted aza-Friedel–Crafts arylation of N-acyliminium ions, generated in situ from o-formyl carbamates and different amines, is reported. This metal-free protocol provides rapid access to diverse 4-aryl 3,4-dihydroquinazolinones in excellent yield without any aqueous workup. A s...

Full description

Saved in:
Bibliographic Details
Published in:ACS omega 2018-10, Vol.3 (10), p.14258-14265
Main Authors: Sawant, Rajiv T, Stevens, Marc Y, Odell, Luke R
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a536t-da39ff7871a54025416f5169214b8f8dc696509d657fa15842f7f9d47ec0b0643
cites cdi_FETCH-LOGICAL-a536t-da39ff7871a54025416f5169214b8f8dc696509d657fa15842f7f9d47ec0b0643
container_end_page 14265
container_issue 10
container_start_page 14258
container_title ACS omega
container_volume 3
creator Sawant, Rajiv T
Stevens, Marc Y
Odell, Luke R
description A one-pot microwave-assisted aza-Friedel–Crafts arylation of N-acyliminium ions, generated in situ from o-formyl carbamates and different amines, is reported. This metal-free protocol provides rapid access to diverse 4-aryl 3,4-dihydroquinazolinones in excellent yield without any aqueous workup. A solvent-directed process for the selective aza-Friedel–Crafts arylation of electron-rich aryl/heteroaryl/butenyl-tethered N-acyliminium ions is also described.
doi_str_mv 10.1021/acsomega.8b02298
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_2af97f718b1b4960862bb6da572603a4</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_2af97f718b1b4960862bb6da572603a4</doaj_id><sourcerecordid>2281854716</sourcerecordid><originalsourceid>FETCH-LOGICAL-a536t-da39ff7871a54025416f5169214b8f8dc696509d657fa15842f7f9d47ec0b0643</originalsourceid><addsrcrecordid>eNp1ks1u1DAUhSMEolXpnhXKkkVTbMd_YYEUTVsYqcAG2Fo3sT31KIkHO2k7XZVHQLxhn4SkMy2dBd7Yss_5bN97kuQ1RscYEfwO6uhbs4BjWSFCCvks2SdUoAznNH_-ZL2XHMa4RAhhLokk_GWyl2PKJMZ8P_n12dXBX8GlycoYXeyNTuEGsrPgjDbN3e2fWQDbx7QM6wZ657vU2_TL3e3vsl43rnWdG9p07rv4Pj29XhntTNenZV2bGNPep3RSjtY0P6LZibtY6-B_Dq6DG9-4zncmvkpeWGiiOdzOB8n3s9Nvs0_Z-deP81l5ngHLeZ9pyAtrhRQYGEWEUcwtw7wgmFbSSl3zgjNUaM6EBcwkJVbYQlNhalQhTvODZL7hag9LtQquhbBWHpy63_BhoSD0rm6MImALYQWWFa5owZHkpKq4BiYIRzlMrKMNK16Z1VDt0E7cj_KeNgwq54Vgk_zDRj5qW6PrsUQBmh3X7knnLtTCXyrO6TjwCHi7BUzVM7FXrYu1aRrojB-iIkRiyajAfJSijXRsa4zB2MdrMFJTbtRDbtQ2N6PlzdPnPRoeUvLvu6NVLf0QurFR_-f9BQNE0rg</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2281854716</pqid></control><display><type>article</type><title>Microwave-Assisted aza-Friedel–Crafts Arylation of N‑Acyliminium Ions: Expedient Access to 4‑Aryl 3,4-Dihydroquinazolinones</title><source>Open Access: PubMed Central</source><source>American Chemical Society (ACS) Open Access</source><creator>Sawant, Rajiv T ; Stevens, Marc Y ; Odell, Luke R</creator><creatorcontrib>Sawant, Rajiv T ; Stevens, Marc Y ; Odell, Luke R</creatorcontrib><description>A one-pot microwave-assisted aza-Friedel–Crafts arylation of N-acyliminium ions, generated in situ from o-formyl carbamates and different amines, is reported. This metal-free protocol provides rapid access to diverse 4-aryl 3,4-dihydroquinazolinones in excellent yield without any aqueous workup. A solvent-directed process for the selective aza-Friedel–Crafts arylation of electron-rich aryl/heteroaryl/butenyl-tethered N-acyliminium ions is also described.</description><identifier>ISSN: 2470-1343</identifier><identifier>EISSN: 2470-1343</identifier><identifier>DOI: 10.1021/acsomega.8b02298</identifier><identifier>PMID: 31458116</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>ACS omega, 2018-10, Vol.3 (10), p.14258-14265</ispartof><rights>Copyright © 2018 American Chemical Society 2018 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a536t-da39ff7871a54025416f5169214b8f8dc696509d657fa15842f7f9d47ec0b0643</citedby><cites>FETCH-LOGICAL-a536t-da39ff7871a54025416f5169214b8f8dc696509d657fa15842f7f9d47ec0b0643</cites><orcidid>0000-0001-7658-5103</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acsomega.8b02298$$EPDF$$P50$$Gacs$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acsomega.8b02298$$EHTML$$P50$$Gacs$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27059,27903,27904,53769,53771,56740,56790</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31458116$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-369754$$DView record from Swedish Publication Index$$Hfree_for_read</backlink></links><search><creatorcontrib>Sawant, Rajiv T</creatorcontrib><creatorcontrib>Stevens, Marc Y</creatorcontrib><creatorcontrib>Odell, Luke R</creatorcontrib><title>Microwave-Assisted aza-Friedel–Crafts Arylation of N‑Acyliminium Ions: Expedient Access to 4‑Aryl 3,4-Dihydroquinazolinones</title><title>ACS omega</title><addtitle>ACS Omega</addtitle><description>A one-pot microwave-assisted aza-Friedel–Crafts arylation of N-acyliminium ions, generated in situ from o-formyl carbamates and different amines, is reported. This metal-free protocol provides rapid access to diverse 4-aryl 3,4-dihydroquinazolinones in excellent yield without any aqueous workup. A solvent-directed process for the selective aza-Friedel–Crafts arylation of electron-rich aryl/heteroaryl/butenyl-tethered N-acyliminium ions is also described.</description><issn>2470-1343</issn><issn>2470-1343</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>N~.</sourceid><sourceid>DOA</sourceid><recordid>eNp1ks1u1DAUhSMEolXpnhXKkkVTbMd_YYEUTVsYqcAG2Fo3sT31KIkHO2k7XZVHQLxhn4SkMy2dBd7Yss_5bN97kuQ1RscYEfwO6uhbs4BjWSFCCvks2SdUoAznNH_-ZL2XHMa4RAhhLokk_GWyl2PKJMZ8P_n12dXBX8GlycoYXeyNTuEGsrPgjDbN3e2fWQDbx7QM6wZ657vU2_TL3e3vsl43rnWdG9p07rv4Pj29XhntTNenZV2bGNPep3RSjtY0P6LZibtY6-B_Dq6DG9-4zncmvkpeWGiiOdzOB8n3s9Nvs0_Z-deP81l5ngHLeZ9pyAtrhRQYGEWEUcwtw7wgmFbSSl3zgjNUaM6EBcwkJVbYQlNhalQhTvODZL7hag9LtQquhbBWHpy63_BhoSD0rm6MImALYQWWFa5owZHkpKq4BiYIRzlMrKMNK16Z1VDt0E7cj_KeNgwq54Vgk_zDRj5qW6PrsUQBmh3X7knnLtTCXyrO6TjwCHi7BUzVM7FXrYu1aRrojB-iIkRiyajAfJSijXRsa4zB2MdrMFJTbtRDbtQ2N6PlzdPnPRoeUvLvu6NVLf0QurFR_-f9BQNE0rg</recordid><startdate>20181031</startdate><enddate>20181031</enddate><creator>Sawant, Rajiv T</creator><creator>Stevens, Marc Y</creator><creator>Odell, Luke R</creator><general>American Chemical Society</general><scope>N~.</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><scope>ACNBI</scope><scope>ADTPV</scope><scope>AOWAS</scope><scope>D8T</scope><scope>DF2</scope><scope>ZZAVC</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0001-7658-5103</orcidid></search><sort><creationdate>20181031</creationdate><title>Microwave-Assisted aza-Friedel–Crafts Arylation of N‑Acyliminium Ions: Expedient Access to 4‑Aryl 3,4-Dihydroquinazolinones</title><author>Sawant, Rajiv T ; Stevens, Marc Y ; Odell, Luke R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a536t-da39ff7871a54025416f5169214b8f8dc696509d657fa15842f7f9d47ec0b0643</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sawant, Rajiv T</creatorcontrib><creatorcontrib>Stevens, Marc Y</creatorcontrib><creatorcontrib>Odell, Luke R</creatorcontrib><collection>American Chemical Society (ACS) Open Access</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>SWEPUB Uppsala universitet full text</collection><collection>SwePub</collection><collection>SwePub Articles</collection><collection>SWEPUB Freely available online</collection><collection>SWEPUB Uppsala universitet</collection><collection>SwePub Articles full text</collection><collection>Directory of Open Access Journals</collection><jtitle>ACS omega</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sawant, Rajiv T</au><au>Stevens, Marc Y</au><au>Odell, Luke R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-Assisted aza-Friedel–Crafts Arylation of N‑Acyliminium Ions: Expedient Access to 4‑Aryl 3,4-Dihydroquinazolinones</atitle><jtitle>ACS omega</jtitle><addtitle>ACS Omega</addtitle><date>2018-10-31</date><risdate>2018</risdate><volume>3</volume><issue>10</issue><spage>14258</spage><epage>14265</epage><pages>14258-14265</pages><issn>2470-1343</issn><eissn>2470-1343</eissn><abstract>A one-pot microwave-assisted aza-Friedel–Crafts arylation of N-acyliminium ions, generated in situ from o-formyl carbamates and different amines, is reported. This metal-free protocol provides rapid access to diverse 4-aryl 3,4-dihydroquinazolinones in excellent yield without any aqueous workup. A solvent-directed process for the selective aza-Friedel–Crafts arylation of electron-rich aryl/heteroaryl/butenyl-tethered N-acyliminium ions is also described.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31458116</pmid><doi>10.1021/acsomega.8b02298</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-7658-5103</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 2470-1343
ispartof ACS omega, 2018-10, Vol.3 (10), p.14258-14265
issn 2470-1343
2470-1343
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_2af97f718b1b4960862bb6da572603a4
source Open Access: PubMed Central; American Chemical Society (ACS) Open Access
title Microwave-Assisted aza-Friedel–Crafts Arylation of N‑Acyliminium Ions: Expedient Access to 4‑Aryl 3,4-Dihydroquinazolinones
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-26T12%3A44%3A30IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Microwave-Assisted%20aza-Friedel%E2%80%93Crafts%20Arylation%20of%20N%E2%80%91Acyliminium%20Ions:%20Expedient%20Access%20to%204%E2%80%91Aryl%203,4-Dihydroquinazolinones&rft.jtitle=ACS%20omega&rft.au=Sawant,%20Rajiv%20T&rft.date=2018-10-31&rft.volume=3&rft.issue=10&rft.spage=14258&rft.epage=14265&rft.pages=14258-14265&rft.issn=2470-1343&rft.eissn=2470-1343&rft_id=info:doi/10.1021/acsomega.8b02298&rft_dat=%3Cproquest_doaj_%3E2281854716%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a536t-da39ff7871a54025416f5169214b8f8dc696509d657fa15842f7f9d47ec0b0643%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2281854716&rft_id=info:pmid/31458116&rfr_iscdi=true