Cu–N‐heterocyclic carbene‐catalysed synthesis of 2‐aryl‐3‐(arylethynyl)quinoxalines from one‐pot tandem coupling of o‐phenylenediamines and terminal alkynes
A series of new benzimidazolium chlorides bearing N,N′‐benzyl, 2,4,6‐trimethylbenzyl and 2,4,6‐triisopropylbenzyl substituents have been designed and synthesized from various o‐phenylenediamines. Subsequently, corresponding Cu‐based N‐heterocyclic carbenes (NHCs) were generated in situ in the reacti...
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Veröffentlicht in: | Applied organometallic chemistry 2019-11, Vol.33 (11), p.n/a |
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creator | Motakatla, Venkata Krishna Reddy Gokanapalli, Anusha Peddiahgari, Vasu Govardhana Reddy |
description | A series of new benzimidazolium chlorides bearing N,N′‐benzyl, 2,4,6‐trimethylbenzyl and 2,4,6‐triisopropylbenzyl substituents have been designed and synthesized from various o‐phenylenediamines. Subsequently, corresponding Cu‐based N‐heterocyclic carbenes (NHCs) were generated in situ in the reaction medium which represents a new application of NHCs exploiting distinct catalytic property towards intermolecular cyclization reaction cascade for the synthesis of 2‐aryl‐3‐(arylethynyl)quinoxalines from o‐phenylenediamines and terminal alkynes. The outcome of the cyclization reaction product depends upon the N,N′‐substituents present on the benzimidazolium chlorides.
Efficient tandem C–N and C–C bond formations among o‐phenylenediamines and terminal alkynes catalysed by Cu–NHCs towards construction of new quinoxaline derivatives are reported. |
doi_str_mv | 10.1002/aoc.5188 |
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Efficient tandem C–N and C–C bond formations among o‐phenylenediamines and terminal alkynes catalysed by Cu–NHCs towards construction of new quinoxaline derivatives are reported.</description><identifier>ISSN: 0268-2605</identifier><identifier>EISSN: 1099-0739</identifier><identifier>DOI: 10.1002/aoc.5188</identifier><language>eng</language><publisher>Chichester: Wiley Subscription Services, Inc</publisher><subject>2‐aryl‐3‐(arylethynyl)quinoxalines ; Alkynes ; Aromatic compounds ; benzimidazolium NHCs ; Carbenes ; Chemical synthesis ; Chemistry ; Chlorides ; intermolecular cyclization ; phenylenediamines ; Quinoxalines ; Reaction products ; terminal alkynes</subject><ispartof>Applied organometallic chemistry, 2019-11, Vol.33 (11), p.n/a</ispartof><rights>2019 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3308-307e87e77f2205ef748df86cd53497f2f724eb1a985c5de0b4313637c296221a3</citedby><cites>FETCH-LOGICAL-c3308-307e87e77f2205ef748df86cd53497f2f724eb1a985c5de0b4313637c296221a3</cites><orcidid>0000-0001-8837-0847</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Faoc.5188$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Faoc.5188$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids></links><search><creatorcontrib>Motakatla, Venkata Krishna Reddy</creatorcontrib><creatorcontrib>Gokanapalli, Anusha</creatorcontrib><creatorcontrib>Peddiahgari, Vasu Govardhana Reddy</creatorcontrib><title>Cu–N‐heterocyclic carbene‐catalysed synthesis of 2‐aryl‐3‐(arylethynyl)quinoxalines from one‐pot tandem coupling of o‐phenylenediamines and terminal alkynes</title><title>Applied organometallic chemistry</title><description>A series of new benzimidazolium chlorides bearing N,N′‐benzyl, 2,4,6‐trimethylbenzyl and 2,4,6‐triisopropylbenzyl substituents have been designed and synthesized from various o‐phenylenediamines. Subsequently, corresponding Cu‐based N‐heterocyclic carbenes (NHCs) were generated in situ in the reaction medium which represents a new application of NHCs exploiting distinct catalytic property towards intermolecular cyclization reaction cascade for the synthesis of 2‐aryl‐3‐(arylethynyl)quinoxalines from o‐phenylenediamines and terminal alkynes. The outcome of the cyclization reaction product depends upon the N,N′‐substituents present on the benzimidazolium chlorides.
Efficient tandem C–N and C–C bond formations among o‐phenylenediamines and terminal alkynes catalysed by Cu–NHCs towards construction of new quinoxaline derivatives are reported.</description><subject>2‐aryl‐3‐(arylethynyl)quinoxalines</subject><subject>Alkynes</subject><subject>Aromatic compounds</subject><subject>benzimidazolium NHCs</subject><subject>Carbenes</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chlorides</subject><subject>intermolecular cyclization</subject><subject>phenylenediamines</subject><subject>Quinoxalines</subject><subject>Reaction products</subject><subject>terminal alkynes</subject><issn>0268-2605</issn><issn>1099-0739</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kUtOwzAQhi0EEqUgcQRLbMoi4EcezrKqeEkVbGAduc6EBty42Ikgux4BiWtwKk7CpGXLwhrP_N-MR_4JOeXsgjMmLrUzFwlXao-MOMvziGUy3ycjJlIViZQlh-QohBfGWJ7yeES-Z93P5uv-Z_O5hBa8M72xtaFG-wU0gGWjW237ACUNfdMuIdSBuooKlLTvLQaJZzLcoV32TW_P37q6cR_a1g0EWnm3om47au1a2uqmhBU1rluj_jyMcoO0BOzEF8tar7Z9yFFcCBNtqbavPRaPyUGlbYCTvzgmT9dXj7PbaP5wczebziMjJVORZBmoDLKsEoIlUGWxKiuVmjKRcY7FKhMxLLjOVWKSEtgillymMjMiT4XgWo7J2W7u2ru3DkJbvLjO4yKhEJLlPFVpLJCa7CjjXQgeqmLt6xV-RMFZMXhRoBfF4AWi0Q59ry30_3LF9GG25X8BOa-V7w</recordid><startdate>201911</startdate><enddate>201911</enddate><creator>Motakatla, Venkata Krishna Reddy</creator><creator>Gokanapalli, Anusha</creator><creator>Peddiahgari, Vasu Govardhana Reddy</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-8837-0847</orcidid></search><sort><creationdate>201911</creationdate><title>Cu–N‐heterocyclic carbene‐catalysed synthesis of 2‐aryl‐3‐(arylethynyl)quinoxalines from one‐pot tandem coupling of o‐phenylenediamines and terminal alkynes</title><author>Motakatla, Venkata Krishna Reddy ; Gokanapalli, Anusha ; Peddiahgari, Vasu Govardhana Reddy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3308-307e87e77f2205ef748df86cd53497f2f724eb1a985c5de0b4313637c296221a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>2‐aryl‐3‐(arylethynyl)quinoxalines</topic><topic>Alkynes</topic><topic>Aromatic compounds</topic><topic>benzimidazolium NHCs</topic><topic>Carbenes</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chlorides</topic><topic>intermolecular cyclization</topic><topic>phenylenediamines</topic><topic>Quinoxalines</topic><topic>Reaction products</topic><topic>terminal alkynes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Motakatla, Venkata Krishna Reddy</creatorcontrib><creatorcontrib>Gokanapalli, Anusha</creatorcontrib><creatorcontrib>Peddiahgari, Vasu Govardhana Reddy</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Applied organometallic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Motakatla, Venkata Krishna Reddy</au><au>Gokanapalli, Anusha</au><au>Peddiahgari, Vasu Govardhana Reddy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cu–N‐heterocyclic carbene‐catalysed synthesis of 2‐aryl‐3‐(arylethynyl)quinoxalines from one‐pot tandem coupling of o‐phenylenediamines and terminal alkynes</atitle><jtitle>Applied organometallic chemistry</jtitle><date>2019-11</date><risdate>2019</risdate><volume>33</volume><issue>11</issue><epage>n/a</epage><issn>0268-2605</issn><eissn>1099-0739</eissn><abstract>A series of new benzimidazolium chlorides bearing N,N′‐benzyl, 2,4,6‐trimethylbenzyl and 2,4,6‐triisopropylbenzyl substituents have been designed and synthesized from various o‐phenylenediamines. Subsequently, corresponding Cu‐based N‐heterocyclic carbenes (NHCs) were generated in situ in the reaction medium which represents a new application of NHCs exploiting distinct catalytic property towards intermolecular cyclization reaction cascade for the synthesis of 2‐aryl‐3‐(arylethynyl)quinoxalines from o‐phenylenediamines and terminal alkynes. The outcome of the cyclization reaction product depends upon the N,N′‐substituents present on the benzimidazolium chlorides.
Efficient tandem C–N and C–C bond formations among o‐phenylenediamines and terminal alkynes catalysed by Cu–NHCs towards construction of new quinoxaline derivatives are reported.</abstract><cop>Chichester</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/aoc.5188</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-8837-0847</orcidid></addata></record> |
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subjects | 2‐aryl‐3‐(arylethynyl)quinoxalines Alkynes Aromatic compounds benzimidazolium NHCs Carbenes Chemical synthesis Chemistry Chlorides intermolecular cyclization phenylenediamines Quinoxalines Reaction products terminal alkynes |
title | Cu–N‐heterocyclic carbene‐catalysed synthesis of 2‐aryl‐3‐(arylethynyl)quinoxalines from one‐pot tandem coupling of o‐phenylenediamines and terminal alkynes |
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