Novel Synthesis of Functionalized Bis(Benzo‐Heterocyclic Amine) Derivatives via Copper‐Catalyzed One‐Pot Multicomponent Reactions

A copper‐catalyzed one‐pot synthesis of substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine is described via intramolecular cyclization of iodophenol and 2‐amino benzimidazoles(thiazoles)(oxazoles)‐trichloroacetonitrile adduct under ultrasound...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:ChemistrySelect (Weinheim) 2024-07, Vol.9 (27), p.n/a
1. Verfasser: Nematpour, Manijeh
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page n/a
container_issue 27
container_start_page
container_title ChemistrySelect (Weinheim)
container_volume 9
creator Nematpour, Manijeh
description A copper‐catalyzed one‐pot synthesis of substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine is described via intramolecular cyclization of iodophenol and 2‐amino benzimidazoles(thiazoles)(oxazoles)‐trichloroacetonitrile adduct under ultrasound irradiation in MeCN with good yields. The use of simple and readily available starting materials, no column chromatography, mild copper‐catalytic reaction conditions, good yields (74–84 %), applying the sonochemical methodology and short reaction times are remarkable specifications of this protocol. All the compounds synthesized in this design are new and their identities have been confirmed using IR, NMR, CHN and mass spectrometry techniques. The protocol detailed in the study for the copper‐catalyzed one‐pot synthesis of various substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine represents a significant advancement in synthetic methodology. By utilizing the intramolecular cyclization of iodophenol and 2‐aminobenzimidazoles (thiazoles/oxazoles) in the presence of trichloroacetonitrile adduct under ultrasound irradiation in MeCN have developed a novel approach to to access these important compounds efficiently. The method offers several advantages, including short reaction times, mild reaction conditions, straightforward work‐up procedures, and readily available starting materials and catalysts.
doi_str_mv 10.1002/slct.202400871
format Article
fullrecord <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_slct_202400871</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>SLCT202400871</sourcerecordid><originalsourceid>FETCH-LOGICAL-c1741-6cb5ff14a19d98c4570f23c95601b87c1cea2084629d595a697294767fb11f263</originalsourceid><addsrcrecordid>eNqFkLFOwzAQhiMEElXpyuwRhhTbje14bAOlSIUiWubIdS_CyI2r2A1KJzZWnpEnoaUI2JjuTvq__6Qvik4J7hKM6YW3OnQppgnGqSAHUYv2OIs5S-Thn_046nj_jDEmPOWUiVb0dudqsGjalOEJvPHIFWi4LnUwrlTWbGCBBsafDaDcuI_X9xEEqJxutDUa9ZemhHN0CZWpVTA1eFQbhTK3WkG1DWcqKNvsKiYlbO97F9Dt2gaj3XLlSigDegD19cqfREeFsh4637MdPQ6vZtkoHk-ub7L-ONZEJCTmes6KgiSKyIVMdcIELmhPS8YxmadCEw2K4jThVC6YZIpLQWUiuCjmhBSU99pRd9-rK-d9BUW-qsxSVU1OcL4zme9M5j8mt4DcAy_GQvNPOp-Os9kv-wnOuH0M</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Novel Synthesis of Functionalized Bis(Benzo‐Heterocyclic Amine) Derivatives via Copper‐Catalyzed One‐Pot Multicomponent Reactions</title><source>Wiley Journals</source><creator>Nematpour, Manijeh</creator><creatorcontrib>Nematpour, Manijeh</creatorcontrib><description>A copper‐catalyzed one‐pot synthesis of substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine is described via intramolecular cyclization of iodophenol and 2‐amino benzimidazoles(thiazoles)(oxazoles)‐trichloroacetonitrile adduct under ultrasound irradiation in MeCN with good yields. The use of simple and readily available starting materials, no column chromatography, mild copper‐catalytic reaction conditions, good yields (74–84 %), applying the sonochemical methodology and short reaction times are remarkable specifications of this protocol. All the compounds synthesized in this design are new and their identities have been confirmed using IR, NMR, CHN and mass spectrometry techniques. The protocol detailed in the study for the copper‐catalyzed one‐pot synthesis of various substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine represents a significant advancement in synthetic methodology. By utilizing the intramolecular cyclization of iodophenol and 2‐aminobenzimidazoles (thiazoles/oxazoles) in the presence of trichloroacetonitrile adduct under ultrasound irradiation in MeCN have developed a novel approach to to access these important compounds efficiently. The method offers several advantages, including short reaction times, mild reaction conditions, straightforward work‐up procedures, and readily available starting materials and catalysts.</description><identifier>ISSN: 2365-6549</identifier><identifier>EISSN: 2365-6549</identifier><identifier>DOI: 10.1002/slct.202400871</identifier><language>eng</language><subject>Bis(benzoxazole)amine ; Copper-Catalyzed ; Iodophenol ; N-Benzoxazole(benzoimidazole)amine ; N-Benzoxazole(benzothiazole)amine ; Trichloroacetonitrile ; Ullmann Coupling ; Ultrasound-assisted</subject><ispartof>ChemistrySelect (Weinheim), 2024-07, Vol.9 (27), p.n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1741-6cb5ff14a19d98c4570f23c95601b87c1cea2084629d595a697294767fb11f263</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fslct.202400871$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fslct.202400871$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Nematpour, Manijeh</creatorcontrib><title>Novel Synthesis of Functionalized Bis(Benzo‐Heterocyclic Amine) Derivatives via Copper‐Catalyzed One‐Pot Multicomponent Reactions</title><title>ChemistrySelect (Weinheim)</title><description>A copper‐catalyzed one‐pot synthesis of substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine is described via intramolecular cyclization of iodophenol and 2‐amino benzimidazoles(thiazoles)(oxazoles)‐trichloroacetonitrile adduct under ultrasound irradiation in MeCN with good yields. The use of simple and readily available starting materials, no column chromatography, mild copper‐catalytic reaction conditions, good yields (74–84 %), applying the sonochemical methodology and short reaction times are remarkable specifications of this protocol. All the compounds synthesized in this design are new and their identities have been confirmed using IR, NMR, CHN and mass spectrometry techniques. The protocol detailed in the study for the copper‐catalyzed one‐pot synthesis of various substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine represents a significant advancement in synthetic methodology. By utilizing the intramolecular cyclization of iodophenol and 2‐aminobenzimidazoles (thiazoles/oxazoles) in the presence of trichloroacetonitrile adduct under ultrasound irradiation in MeCN have developed a novel approach to to access these important compounds efficiently. The method offers several advantages, including short reaction times, mild reaction conditions, straightforward work‐up procedures, and readily available starting materials and catalysts.</description><subject>Bis(benzoxazole)amine</subject><subject>Copper-Catalyzed</subject><subject>Iodophenol</subject><subject>N-Benzoxazole(benzoimidazole)amine</subject><subject>N-Benzoxazole(benzothiazole)amine</subject><subject>Trichloroacetonitrile</subject><subject>Ullmann Coupling</subject><subject>Ultrasound-assisted</subject><issn>2365-6549</issn><issn>2365-6549</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOwzAQhiMEElXpyuwRhhTbje14bAOlSIUiWubIdS_CyI2r2A1KJzZWnpEnoaUI2JjuTvq__6Qvik4J7hKM6YW3OnQppgnGqSAHUYv2OIs5S-Thn_046nj_jDEmPOWUiVb0dudqsGjalOEJvPHIFWi4LnUwrlTWbGCBBsafDaDcuI_X9xEEqJxutDUa9ZemhHN0CZWpVTA1eFQbhTK3WkG1DWcqKNvsKiYlbO97F9Dt2gaj3XLlSigDegD19cqfREeFsh4637MdPQ6vZtkoHk-ub7L-ONZEJCTmes6KgiSKyIVMdcIELmhPS8YxmadCEw2K4jThVC6YZIpLQWUiuCjmhBSU99pRd9-rK-d9BUW-qsxSVU1OcL4zme9M5j8mt4DcAy_GQvNPOp-Os9kv-wnOuH0M</recordid><startdate>20240718</startdate><enddate>20240718</enddate><creator>Nematpour, Manijeh</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20240718</creationdate><title>Novel Synthesis of Functionalized Bis(Benzo‐Heterocyclic Amine) Derivatives via Copper‐Catalyzed One‐Pot Multicomponent Reactions</title><author>Nematpour, Manijeh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1741-6cb5ff14a19d98c4570f23c95601b87c1cea2084629d595a697294767fb11f263</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Bis(benzoxazole)amine</topic><topic>Copper-Catalyzed</topic><topic>Iodophenol</topic><topic>N-Benzoxazole(benzoimidazole)amine</topic><topic>N-Benzoxazole(benzothiazole)amine</topic><topic>Trichloroacetonitrile</topic><topic>Ullmann Coupling</topic><topic>Ultrasound-assisted</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nematpour, Manijeh</creatorcontrib><collection>CrossRef</collection><jtitle>ChemistrySelect (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nematpour, Manijeh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Synthesis of Functionalized Bis(Benzo‐Heterocyclic Amine) Derivatives via Copper‐Catalyzed One‐Pot Multicomponent Reactions</atitle><jtitle>ChemistrySelect (Weinheim)</jtitle><date>2024-07-18</date><risdate>2024</risdate><volume>9</volume><issue>27</issue><epage>n/a</epage><issn>2365-6549</issn><eissn>2365-6549</eissn><abstract>A copper‐catalyzed one‐pot synthesis of substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine is described via intramolecular cyclization of iodophenol and 2‐amino benzimidazoles(thiazoles)(oxazoles)‐trichloroacetonitrile adduct under ultrasound irradiation in MeCN with good yields. The use of simple and readily available starting materials, no column chromatography, mild copper‐catalytic reaction conditions, good yields (74–84 %), applying the sonochemical methodology and short reaction times are remarkable specifications of this protocol. All the compounds synthesized in this design are new and their identities have been confirmed using IR, NMR, CHN and mass spectrometry techniques. The protocol detailed in the study for the copper‐catalyzed one‐pot synthesis of various substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine represents a significant advancement in synthetic methodology. By utilizing the intramolecular cyclization of iodophenol and 2‐aminobenzimidazoles (thiazoles/oxazoles) in the presence of trichloroacetonitrile adduct under ultrasound irradiation in MeCN have developed a novel approach to to access these important compounds efficiently. The method offers several advantages, including short reaction times, mild reaction conditions, straightforward work‐up procedures, and readily available starting materials and catalysts.</abstract><doi>10.1002/slct.202400871</doi><tpages>6</tpages></addata></record>
fulltext fulltext
identifier ISSN: 2365-6549
ispartof ChemistrySelect (Weinheim), 2024-07, Vol.9 (27), p.n/a
issn 2365-6549
2365-6549
language eng
recordid cdi_crossref_primary_10_1002_slct_202400871
source Wiley Journals
subjects Bis(benzoxazole)amine
Copper-Catalyzed
Iodophenol
N-Benzoxazole(benzoimidazole)amine
N-Benzoxazole(benzothiazole)amine
Trichloroacetonitrile
Ullmann Coupling
Ultrasound-assisted
title Novel Synthesis of Functionalized Bis(Benzo‐Heterocyclic Amine) Derivatives via Copper‐Catalyzed One‐Pot Multicomponent Reactions
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T05%3A21%3A04IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Novel%20Synthesis%20of%20Functionalized%20Bis(Benzo%E2%80%90Heterocyclic%20Amine)%20Derivatives%20via%20Copper%E2%80%90Catalyzed%20One%E2%80%90Pot%20Multicomponent%20Reactions&rft.jtitle=ChemistrySelect%20(Weinheim)&rft.au=Nematpour,%20Manijeh&rft.date=2024-07-18&rft.volume=9&rft.issue=27&rft.epage=n/a&rft.issn=2365-6549&rft.eissn=2365-6549&rft_id=info:doi/10.1002/slct.202400871&rft_dat=%3Cwiley_cross%3ESLCT202400871%3C/wiley_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