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A facile and green procedure in preparing dibenzo-chromeno-phenazine-diones using an effectual and recyclable Brønsted acidic ionic liquid
First, a Brønsted acid ionic liquid (BAIL) in the role of a double acid-base called 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT) was produced, and its skeleton was determined via TGA, mass, 13 C NMR, 19 F NMR, 1 H NMR and FT-IR data. Further, it was successfully applied in...
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Published in: | Scientific reports 2024-11, Vol.14 (1), p.26758-12, Article 26758 |
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creator | Hsu, Chou-Yi Abdulkareem, Riyadh Pallathadka, Harikumar Abbot, Vikrant Chahar, Mamata Abduvalieva, Dilsora Mustafa, Yasser Fakri Altimari, Usama S. mhussan jabbar, Abeer Zwamel, Ahmed Hussein |
description | First, a Brønsted acid ionic liquid (BAIL) in the role of a double acid-base called 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT) was produced, and its skeleton was determined via TGA, mass,
13
C NMR,
19
F NMR,
1
H NMR and FT-IR data. Further, it was successfully applied in the preparation of dibenzo-chromeno-phenazine-dione derivatives (
1a
-
12a
, 9–15 min, 90–98%) via one-pot multicomponent domino reaction among 2 mmol 2-hydroxynaphthalene-1,4-dione, 1 mmol benzene-1,2-diamine, and 1 mmol aldehydes under optimal conditions (5 mol% of PBPBSDT, solvent-free, 60 °C). The proper reproducibility of the PBPBSDT homogeneous catalyst (5 times), solvent-free medium, reasonable TON (Turnover Number) and TOF (Turnover Frequency) numbers, the non-metallic framework of the catalyst, and the formation of C-N, C = N, C-C, C = C, C-O bonds in a single operation are the distinct advantages of this protocol. |
doi_str_mv | 10.1038/s41598-024-73257-3 |
format | article |
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13
C NMR,
19
F NMR,
1
H NMR and FT-IR data. Further, it was successfully applied in the preparation of dibenzo-chromeno-phenazine-dione derivatives (
1a
-
12a
, 9–15 min, 90–98%) via one-pot multicomponent domino reaction among 2 mmol 2-hydroxynaphthalene-1,4-dione, 1 mmol benzene-1,2-diamine, and 1 mmol aldehydes under optimal conditions (5 mol% of PBPBSDT, solvent-free, 60 °C). The proper reproducibility of the PBPBSDT homogeneous catalyst (5 times), solvent-free medium, reasonable TON (Turnover Number) and TOF (Turnover Frequency) numbers, the non-metallic framework of the catalyst, and the formation of C-N, C = N, C-C, C = C, C-O bonds in a single operation are the distinct advantages of this protocol.</description><identifier>ISSN: 2045-2322</identifier><identifier>EISSN: 2045-2322</identifier><identifier>DOI: 10.1038/s41598-024-73257-3</identifier><identifier>PMID: 39500919</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>639/638/309 ; 639/638/403 ; 639/638/77 ; Acids ; Aldehydes ; Benzene ; Catalysts ; Chemistry ; Dibenzo-chromeno-phenazine-diones. Multicomponent domino reactions (MCDRs). 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT). Solvent-free medium ; Fourier transforms ; Humanities and Social Sciences ; Hydrocarbons ; Medical laboratories ; multidisciplinary ; NMR ; Nuclear magnetic resonance ; Pharmaceutical industry ; Pharmacy ; Phenazine ; Science ; Science (multidisciplinary) ; Solvents</subject><ispartof>Scientific reports, 2024-11, Vol.14 (1), p.26758-12, Article 26758</ispartof><rights>The Author(s) 2024</rights><rights>2024. The Author(s).</rights><rights>The Author(s) 2024. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>The Author(s) 2024 2024</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c422t-e58dc8501334dfaafa26a42dfe09746acfb3ebed46391c5f02cb09b57c56b8793</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/3124277657/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/3124277657?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39500919$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hsu, Chou-Yi</creatorcontrib><creatorcontrib>Abdulkareem, Riyadh</creatorcontrib><creatorcontrib>Pallathadka, Harikumar</creatorcontrib><creatorcontrib>Abbot, Vikrant</creatorcontrib><creatorcontrib>Chahar, Mamata</creatorcontrib><creatorcontrib>Abduvalieva, Dilsora</creatorcontrib><creatorcontrib>Mustafa, Yasser Fakri</creatorcontrib><creatorcontrib>Altimari, Usama S.</creatorcontrib><creatorcontrib>mhussan jabbar, Abeer</creatorcontrib><creatorcontrib>Zwamel, Ahmed Hussein</creatorcontrib><title>A facile and green procedure in preparing dibenzo-chromeno-phenazine-diones using an effectual and recyclable Brønsted acidic ionic liquid</title><title>Scientific reports</title><addtitle>Sci Rep</addtitle><addtitle>Sci Rep</addtitle><description>First, a Brønsted acid ionic liquid (BAIL) in the role of a double acid-base called 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT) was produced, and its skeleton was determined via TGA, mass,
13
C NMR,
19
F NMR,
1
H NMR and FT-IR data. Further, it was successfully applied in the preparation of dibenzo-chromeno-phenazine-dione derivatives (
1a
-
12a
, 9–15 min, 90–98%) via one-pot multicomponent domino reaction among 2 mmol 2-hydroxynaphthalene-1,4-dione, 1 mmol benzene-1,2-diamine, and 1 mmol aldehydes under optimal conditions (5 mol% of PBPBSDT, solvent-free, 60 °C). The proper reproducibility of the PBPBSDT homogeneous catalyst (5 times), solvent-free medium, reasonable TON (Turnover Number) and TOF (Turnover Frequency) numbers, the non-metallic framework of the catalyst, and the formation of C-N, C = N, C-C, C = C, C-O bonds in a single operation are the distinct advantages of this protocol.</description><subject>639/638/309</subject><subject>639/638/403</subject><subject>639/638/77</subject><subject>Acids</subject><subject>Aldehydes</subject><subject>Benzene</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Dibenzo-chromeno-phenazine-diones. Multicomponent domino reactions (MCDRs). 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT). Solvent-free medium</subject><subject>Fourier transforms</subject><subject>Humanities and Social Sciences</subject><subject>Hydrocarbons</subject><subject>Medical laboratories</subject><subject>multidisciplinary</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Pharmaceutical industry</subject><subject>Pharmacy</subject><subject>Phenazine</subject><subject>Science</subject><subject>Science (multidisciplinary)</subject><subject>Solvents</subject><issn>2045-2322</issn><issn>2045-2322</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNp9ks1u1DAQxyMEotXSF-CAInHhEvBnEp9QqWipVIkLnK2JPdn1KmundoLUvkJfiDsvhndTSsuBOfhrfvMf2_oXxWtK3lPC2w9JUKnaijBRNZzJpuLPimNGhKwYZ-z5o_VRcZLSluSQTAmqXhZHXElCFFXHxd1p2YNxA5bgbbmOiL4cYzBo54il229whOj8urSuQ38bKrOJYYc-VOMGPdw6j5V1wWMq57TnwJfY92imGYaDakRzYwbocpNP8ddPnya0ZW5qnSlzYR4Hdz07-6p40cOQ8OR-XhXfzz9_O_tSXX29uDw7vaqMYGyqULbWtJJQzoXtAXpgNQhmeySqETWYvuPYoRU1V9TInjDTEdXJxsi6axvFV8XlomsDbPUY3Q7ijQ7g9OEgxLWGODkzoCYgBLeK1rQFoazoWsMIdARziDrnVsXHRWucux1ag36KMDwRfZrxbqPX4YemVPJWcpYV3t0rxHA9Y5r0ziWDwwAew5w0p0zULa8Fyejbf9BtmKPPf3WgWNPUsskUWygTQ0oR-4fbUKL33tGLd3T2jj54R_Nc9ObxOx5K_jglA3wB0rh3A8a_vf8j-xvfIdKt</recordid><startdate>20241105</startdate><enddate>20241105</enddate><creator>Hsu, Chou-Yi</creator><creator>Abdulkareem, Riyadh</creator><creator>Pallathadka, Harikumar</creator><creator>Abbot, Vikrant</creator><creator>Chahar, Mamata</creator><creator>Abduvalieva, Dilsora</creator><creator>Mustafa, Yasser Fakri</creator><creator>Altimari, Usama S.</creator><creator>mhussan jabbar, Abeer</creator><creator>Zwamel, Ahmed Hussein</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><general>Nature Portfolio</general><scope>C6C</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20241105</creationdate><title>A facile and green procedure in preparing dibenzo-chromeno-phenazine-diones using an effectual and recyclable Brønsted acidic ionic liquid</title><author>Hsu, Chou-Yi ; Abdulkareem, Riyadh ; Pallathadka, Harikumar ; Abbot, Vikrant ; Chahar, Mamata ; Abduvalieva, Dilsora ; Mustafa, Yasser Fakri ; Altimari, Usama S. ; mhussan jabbar, Abeer ; Zwamel, Ahmed Hussein</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c422t-e58dc8501334dfaafa26a42dfe09746acfb3ebed46391c5f02cb09b57c56b8793</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>639/638/309</topic><topic>639/638/403</topic><topic>639/638/77</topic><topic>Acids</topic><topic>Aldehydes</topic><topic>Benzene</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Dibenzo-chromeno-phenazine-diones. Multicomponent domino reactions (MCDRs). 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT). Solvent-free medium</topic><topic>Fourier transforms</topic><topic>Humanities and Social Sciences</topic><topic>Hydrocarbons</topic><topic>Medical laboratories</topic><topic>multidisciplinary</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Pharmaceutical industry</topic><topic>Pharmacy</topic><topic>Phenazine</topic><topic>Science</topic><topic>Science (multidisciplinary)</topic><topic>Solvents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hsu, Chou-Yi</creatorcontrib><creatorcontrib>Abdulkareem, Riyadh</creatorcontrib><creatorcontrib>Pallathadka, Harikumar</creatorcontrib><creatorcontrib>Abbot, Vikrant</creatorcontrib><creatorcontrib>Chahar, Mamata</creatorcontrib><creatorcontrib>Abduvalieva, Dilsora</creatorcontrib><creatorcontrib>Mustafa, Yasser Fakri</creatorcontrib><creatorcontrib>Altimari, Usama S.</creatorcontrib><creatorcontrib>mhussan jabbar, Abeer</creatorcontrib><creatorcontrib>Zwamel, Ahmed Hussein</creatorcontrib><collection>SpringerOpen</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection (Proquest) (PQ_SDU_P3)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>ProQuest Science Journals</collection><collection>Biological Science Database</collection><collection>Publicly Available Content Database</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 Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Scientific reports</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hsu, Chou-Yi</au><au>Abdulkareem, Riyadh</au><au>Pallathadka, Harikumar</au><au>Abbot, Vikrant</au><au>Chahar, Mamata</au><au>Abduvalieva, Dilsora</au><au>Mustafa, Yasser Fakri</au><au>Altimari, Usama S.</au><au>mhussan jabbar, Abeer</au><au>Zwamel, Ahmed Hussein</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A facile and green procedure in preparing dibenzo-chromeno-phenazine-diones using an effectual and recyclable Brønsted acidic ionic liquid</atitle><jtitle>Scientific reports</jtitle><stitle>Sci Rep</stitle><addtitle>Sci Rep</addtitle><date>2024-11-05</date><risdate>2024</risdate><volume>14</volume><issue>1</issue><spage>26758</spage><epage>12</epage><pages>26758-12</pages><artnum>26758</artnum><issn>2045-2322</issn><eissn>2045-2322</eissn><abstract>First, a Brønsted acid ionic liquid (BAIL) in the role of a double acid-base called 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT) was produced, and its skeleton was determined via TGA, mass,
13
C NMR,
19
F NMR,
1
H NMR and FT-IR data. Further, it was successfully applied in the preparation of dibenzo-chromeno-phenazine-dione derivatives (
1a
-
12a
, 9–15 min, 90–98%) via one-pot multicomponent domino reaction among 2 mmol 2-hydroxynaphthalene-1,4-dione, 1 mmol benzene-1,2-diamine, and 1 mmol aldehydes under optimal conditions (5 mol% of PBPBSDT, solvent-free, 60 °C). The proper reproducibility of the PBPBSDT homogeneous catalyst (5 times), solvent-free medium, reasonable TON (Turnover Number) and TOF (Turnover Frequency) numbers, the non-metallic framework of the catalyst, and the formation of C-N, C = N, C-C, C = C, C-O bonds in a single operation are the distinct advantages of this protocol.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>39500919</pmid><doi>10.1038/s41598-024-73257-3</doi><tpages>12</tpages><oa>free_for_read</oa></addata></record> |
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subjects | 639/638/309 639/638/403 639/638/77 Acids Aldehydes Benzene Catalysts Chemistry Dibenzo-chromeno-phenazine-diones. Multicomponent domino reactions (MCDRs). 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT). Solvent-free medium Fourier transforms Humanities and Social Sciences Hydrocarbons Medical laboratories multidisciplinary NMR Nuclear magnetic resonance Pharmaceutical industry Pharmacy Phenazine Science Science (multidisciplinary) Solvents |
title | A facile and green procedure in preparing dibenzo-chromeno-phenazine-diones using an effectual and recyclable Brønsted acidic ionic liquid |
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