Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1‐Methyl‐8‐dimethylamino‐10‐phenylphenazin‐2‐(10H)one and Related Compounds

Oxidative condensation of three p‐phenylenediamines with 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene gives new coloured aposafranones. 2‐Methylresorcinol is easy to convert into the asymmetric building block 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene with aniline. The aposafranones are sterically crowd...

Full description

Saved in:
Bibliographic Details
Published in:ChemistryOpen (Weinheim) 2023-02, Vol.12 (2), p.e202300007-n/a
Main Authors: Plater, M. John, Harrison, William T. A.
Format: Article
Language:English
Subjects:
Aniline
aposafranone
Benzene
Chromatography
chromophores
Free radicals
Hydrocarbons
Iodine
NMR
Nuclear magnetic resonance
phenazinone
safranone
Solvents
X-ray crystallography
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites cdi_FETCH-LOGICAL-c5567-8fa58d3560d81755b42a0819bb000c15106955bcb4f60598fb37fb3a6429d6883
container_end_page n/a
container_issue 2
container_start_page e202300007
container_title ChemistryOpen (Weinheim)
container_volume 12
creator Plater, M. John
Harrison, William T. A.
description Oxidative condensation of three p‐phenylenediamines with 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene gives new coloured aposafranones. 2‐Methylresorcinol is easy to convert into the asymmetric building block 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene with aniline. The aposafranones are sterically crowded because of the 1‐methyl and N‐phenyl groups. The UV/Vis absorption maxima are in the range 530–545 nm. A crowded donor‐acceptor aposafranone has been characterised by an X‐ray single crystal structure determination. Steric bulk is believed to stabilise free radical intermediates and facilitate a free radical cyclisation pathway forming the chromophore.
doi_str_mv 10.1002/open.202300007
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_e0ff11d32b5d4d3da618828ed78453e7</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_e0ff11d32b5d4d3da618828ed78453e7</doaj_id><sourcerecordid>2778874626</sourcerecordid><originalsourceid>FETCH-LOGICAL-c5567-8fa58d3560d81755b42a0819bb000c15106955bcb4f60598fb37fb3a6429d6883</originalsourceid><addsrcrecordid>eNqFkstu1DAUQCMEolXpliWKxKYsZvAjdhwWSNWoMJUKRRTWlmPfdDxK7GAnVGHFJ7Dj__gSPDNlaNkQ6fpxfXxsRzfLnmI0xwiRl74HNyeIUJS-8kF2SHCFZ5hy-vDO-CA7jnG9RYoKM_44O6C8FIRW5DD7uYQBgteTbq3OryY3rCDamPsmXwR_Y8Dkp72PqgnKeQfxVX41hFEPY4ANg399__EOhtXUpoFIYWy3narOOp_mGKWmX4Gb2k2rvlmXEiTFCUbLF0mZK2fyj9CqIZ218F3vR2fik-xRo9oIx7f9Ufb5zdmnxXJ2cfn2fHF6MdOM8XImGsWEoYwjI3DJWF0QhQSu6jo9V2OGEa9SVtdFwxGrRFPTMoXiBakMF4IeZec7r_FqLftgOxUm6ZWV24QP11KFweoWJKCmwdhQUjNTGGoUx0IQAaYUBaNQJtfrnasf6w6MBjcE1d6T3l9xdiWv_VdZVYQJSpLg5FYQ_JcR4iA7GzW0rXLgxyhJWXJGEBMsoc__Qdd-DC79qg0lRFlwwhM131E6-BgDNPvLYCQ3JSQ3JST3JZQ2PLv7hD3-p2ASUO2AG9vC9B-dvPxw9v6v_DfGK9p7</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2778874626</pqid></control><display><type>article</type><title>Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1‐Methyl‐8‐dimethylamino‐10‐phenylphenazin‐2‐(10H)one and Related Compounds</title><source>Open Access: Wiley-Blackwell Open Access Journals</source><source>Publicly Available Content (ProQuest)</source><source>PubMed Central</source><source>Free Full-Text Journals in Chemistry</source><creator>Plater, M. John ; Harrison, William T. A.</creator><creatorcontrib>Plater, M. John ; Harrison, William T. A.</creatorcontrib><description>Oxidative condensation of three p‐phenylenediamines with 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene gives new coloured aposafranones. 2‐Methylresorcinol is easy to convert into the asymmetric building block 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene with aniline. The aposafranones are sterically crowded because of the 1‐methyl and N‐phenyl groups. The UV/Vis absorption maxima are in the range 530–545 nm. A crowded donor‐acceptor aposafranone has been characterised by an X‐ray single crystal structure determination. Steric bulk is believed to stabilise free radical intermediates and facilitate a free radical cyclisation pathway forming the chromophore.</description><identifier>ISSN: 2191-1363</identifier><identifier>EISSN: 2191-1363</identifier><identifier>DOI: 10.1002/open.202300007</identifier><identifier>PMID: 36782392</identifier><language>eng</language><publisher>Germany: John Wiley &amp; Sons, Inc</publisher><subject>Aniline ; aposafranone ; Benzene ; Chromatography ; chromophores ; Free radicals ; Hydrocarbons ; Iodine ; NMR ; Nuclear magnetic resonance ; phenazinone ; safranone ; Solvents ; X-ray crystallography</subject><ispartof>ChemistryOpen (Weinheim), 2023-02, Vol.12 (2), p.e202300007-n/a</ispartof><rights>2023 The Authors. Published by Wiley-VCH GmbH</rights><rights>2023 The Authors. Published by Wiley-VCH GmbH.</rights><rights>2023. This work is published under http://creativecommons.org/licenses/by-nc/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c5567-8fa58d3560d81755b42a0819bb000c15106955bcb4f60598fb37fb3a6429d6883</cites><orcidid>0000-0003-0204-9695</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2778874626/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2778874626?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,11542,25732,27903,27904,36991,36992,44569,46031,46455,53770,53772,74873</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36782392$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Plater, M. John</creatorcontrib><creatorcontrib>Harrison, William T. A.</creatorcontrib><title>Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1‐Methyl‐8‐dimethylamino‐10‐phenylphenazin‐2‐(10H)one and Related Compounds</title><title>ChemistryOpen (Weinheim)</title><addtitle>ChemistryOpen</addtitle><description>Oxidative condensation of three p‐phenylenediamines with 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene gives new coloured aposafranones. 2‐Methylresorcinol is easy to convert into the asymmetric building block 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene with aniline. The aposafranones are sterically crowded because of the 1‐methyl and N‐phenyl groups. The UV/Vis absorption maxima are in the range 530–545 nm. A crowded donor‐acceptor aposafranone has been characterised by an X‐ray single crystal structure determination. Steric bulk is believed to stabilise free radical intermediates and facilitate a free radical cyclisation pathway forming the chromophore.</description><subject>Aniline</subject><subject>aposafranone</subject><subject>Benzene</subject><subject>Chromatography</subject><subject>chromophores</subject><subject>Free radicals</subject><subject>Hydrocarbons</subject><subject>Iodine</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>phenazinone</subject><subject>safranone</subject><subject>Solvents</subject><subject>X-ray crystallography</subject><issn>2191-1363</issn><issn>2191-1363</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNqFkstu1DAUQCMEolXpliWKxKYsZvAjdhwWSNWoMJUKRRTWlmPfdDxK7GAnVGHFJ7Dj__gSPDNlaNkQ6fpxfXxsRzfLnmI0xwiRl74HNyeIUJS-8kF2SHCFZ5hy-vDO-CA7jnG9RYoKM_44O6C8FIRW5DD7uYQBgteTbq3OryY3rCDamPsmXwR_Y8Dkp72PqgnKeQfxVX41hFEPY4ANg399__EOhtXUpoFIYWy3narOOp_mGKWmX4Gb2k2rvlmXEiTFCUbLF0mZK2fyj9CqIZ218F3vR2fik-xRo9oIx7f9Ufb5zdmnxXJ2cfn2fHF6MdOM8XImGsWEoYwjI3DJWF0QhQSu6jo9V2OGEa9SVtdFwxGrRFPTMoXiBakMF4IeZec7r_FqLftgOxUm6ZWV24QP11KFweoWJKCmwdhQUjNTGGoUx0IQAaYUBaNQJtfrnasf6w6MBjcE1d6T3l9xdiWv_VdZVYQJSpLg5FYQ_JcR4iA7GzW0rXLgxyhJWXJGEBMsoc__Qdd-DC79qg0lRFlwwhM131E6-BgDNPvLYCQ3JSQ3JST3JZQ2PLv7hD3-p2ASUO2AG9vC9B-dvPxw9v6v_DfGK9p7</recordid><startdate>202302</startdate><enddate>202302</enddate><creator>Plater, M. John</creator><creator>Harrison, William T. A.</creator><general>John Wiley &amp; Sons, Inc</general><general>John Wiley and Sons Inc</general><general>Wiley-VCH</general><scope>24P</scope><scope>WIN</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>L6V</scope><scope>L7M</scope><scope>M7S</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0003-0204-9695</orcidid></search><sort><creationdate>202302</creationdate><title>Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1‐Methyl‐8‐dimethylamino‐10‐phenylphenazin‐2‐(10H)one and Related Compounds</title><author>Plater, M. John ; Harrison, William T. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5567-8fa58d3560d81755b42a0819bb000c15106955bcb4f60598fb37fb3a6429d6883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aniline</topic><topic>aposafranone</topic><topic>Benzene</topic><topic>Chromatography</topic><topic>chromophores</topic><topic>Free radicals</topic><topic>Hydrocarbons</topic><topic>Iodine</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>phenazinone</topic><topic>safranone</topic><topic>Solvents</topic><topic>X-ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Plater, M. John</creatorcontrib><creatorcontrib>Harrison, William T. A.</creatorcontrib><collection>Open Access: Wiley-Blackwell Open Access Journals</collection><collection>Wiley Online Library Free Content</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science &amp; Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>ProQuest Engineering Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Engineering Database</collection><collection>Materials Science Collection</collection><collection>Publicly Available Content (ProQuest)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>Engineering collection</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>ChemistryOpen (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Plater, M. John</au><au>Harrison, William T. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1‐Methyl‐8‐dimethylamino‐10‐phenylphenazin‐2‐(10H)one and Related Compounds</atitle><jtitle>ChemistryOpen (Weinheim)</jtitle><addtitle>ChemistryOpen</addtitle><date>2023-02</date><risdate>2023</risdate><volume>12</volume><issue>2</issue><spage>e202300007</spage><epage>n/a</epage><pages>e202300007-n/a</pages><issn>2191-1363</issn><eissn>2191-1363</eissn><abstract>Oxidative condensation of three p‐phenylenediamines with 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene gives new coloured aposafranones. 2‐Methylresorcinol is easy to convert into the asymmetric building block 3‐hydroxy‐2‐methyl‐N‐(phenylamino)benzene with aniline. The aposafranones are sterically crowded because of the 1‐methyl and N‐phenyl groups. The UV/Vis absorption maxima are in the range 530–545 nm. A crowded donor‐acceptor aposafranone has been characterised by an X‐ray single crystal structure determination. Steric bulk is believed to stabilise free radical intermediates and facilitate a free radical cyclisation pathway forming the chromophore.</abstract><cop>Germany</cop><pub>John Wiley &amp; Sons, Inc</pub><pmid>36782392</pmid><doi>10.1002/open.202300007</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-0204-9695</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 2191-1363
ispartof ChemistryOpen (Weinheim), 2023-02, Vol.12 (2), p.e202300007-n/a
issn 2191-1363
2191-1363
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_e0ff11d32b5d4d3da618828ed78453e7
source Open Access: Wiley-Blackwell Open Access Journals; Publicly Available Content (ProQuest); PubMed Central; Free Full-Text Journals in Chemistry
subjects Aniline
aposafranone
Benzene
Chromatography
chromophores
Free radicals
Hydrocarbons
Iodine
NMR
Nuclear magnetic resonance
phenazinone
safranone
Solvents
X-ray crystallography
title Heterocyclic Synthesis of Crowded Aposafranones: Structure of 1‐Methyl‐8‐dimethylamino‐10‐phenylphenazin‐2‐(10H)one and Related Compounds
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-23T05%3A21%3A12IST&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=Heterocyclic%20Synthesis%20of%20Crowded%20Aposafranones:%20Structure%20of%201%E2%80%90Methyl%E2%80%908%E2%80%90dimethylamino%E2%80%9010%E2%80%90phenylphenazin%E2%80%902%E2%80%90(10H)one%20and%20Related%20Compounds&rft.jtitle=ChemistryOpen%20(Weinheim)&rft.au=Plater,%20M.%20John&rft.date=2023-02&rft.volume=12&rft.issue=2&rft.spage=e202300007&rft.epage=n/a&rft.pages=e202300007-n/a&rft.issn=2191-1363&rft.eissn=2191-1363&rft_id=info:doi/10.1002/open.202300007&rft_dat=%3Cproquest_doaj_%3E2778874626%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c5567-8fa58d3560d81755b42a0819bb000c15106955bcb4f60598fb37fb3a6429d6883%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2778874626&rft_id=info:pmid/36782392&rfr_iscdi=true