One‐pot Sequential Strategy to Prepare Organoselanyl and Organotellanyl Isoquinolinium Imides
Herein, we report an efficient, transition‐metal‐free and practical one‐pot sequential method for the synthesis of organochalcogenyl isoquinolinium imides. In this one‐pot two‐steps approach, N′‐(2‐alkynylbenzylidene) hydrazides were firstly prepared under ultrasound irradiation, followed by the add...
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Veröffentlicht in: | European journal of organic chemistry 2022-11, Vol.2022 (43), p.n/a |
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container_title | European journal of organic chemistry |
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creator | Goulart, Helen A. Araujo, Daniela R. Barcellos, Angelita M. Jacob, Raquel G. Lenardão, Eder J. Perin, Gelson |
description | Herein, we report an efficient, transition‐metal‐free and practical one‐pot sequential method for the synthesis of organochalcogenyl isoquinolinium imides. In this one‐pot two‐steps approach, N′‐(2‐alkynylbenzylidene) hydrazides were firstly prepared under ultrasound irradiation, followed by the addition of diorganyl dichalcogenides and Oxone®. A total of 25 organoselanyl isoquinolinium imides, being 22 unprecedented in the literature, were obtained in good to excellent yields (79–95 %) in short reaction times (30–70 min) using a range of 2‐alkynyl aldehydes and diaryl, dialkyl, and diheteroaryl diselenides as substrates. The methodology was extended to tellurium, affording for the first time, tellurium isoquinolinium imides, in good yields (70–80 %) after 120 min of reaction.
Here report a one‐pot two‐steps approach to prepare organoselanyl and organotellanyl isoquinolinium imides by the 6‐endo‐dig electrophilic cyclization of N′‐(2‐alkynylbenzylidene)hydrazides using diorganyl diselenides/ditellurides and Oxone® under ultrasound irradiation. |
doi_str_mv | 10.1002/ejoc.202201027 |
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Here report a one‐pot two‐steps approach to prepare organoselanyl and organotellanyl isoquinolinium imides by the 6‐endo‐dig electrophilic cyclization of N′‐(2‐alkynylbenzylidene)hydrazides using diorganyl diselenides/ditellurides and Oxone® under ultrasound irradiation.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202201027</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Aldehydes ; Cyclization ; Green Chemistry ; Hydrazides ; Imides ; Isoquinoline ; Selenides ; Selenium ; Substrates ; Tellurium</subject><ispartof>European journal of organic chemistry, 2022-11, Vol.2022 (43), p.n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3177-d1fe75a84581cfd16dc5b3fd9372ca950a776534edea4e80f08dcb07eb0d0ff63</citedby><cites>FETCH-LOGICAL-c3177-d1fe75a84581cfd16dc5b3fd9372ca950a776534edea4e80f08dcb07eb0d0ff63</cites><orcidid>0000-0003-0359-0811</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%2Fejoc.202201027$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202201027$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Goulart, Helen A.</creatorcontrib><creatorcontrib>Araujo, Daniela R.</creatorcontrib><creatorcontrib>Barcellos, Angelita M.</creatorcontrib><creatorcontrib>Jacob, Raquel G.</creatorcontrib><creatorcontrib>Lenardão, Eder J.</creatorcontrib><creatorcontrib>Perin, Gelson</creatorcontrib><title>One‐pot Sequential Strategy to Prepare Organoselanyl and Organotellanyl Isoquinolinium Imides</title><title>European journal of organic chemistry</title><description>Herein, we report an efficient, transition‐metal‐free and practical one‐pot sequential method for the synthesis of organochalcogenyl isoquinolinium imides. In this one‐pot two‐steps approach, N′‐(2‐alkynylbenzylidene) hydrazides were firstly prepared under ultrasound irradiation, followed by the addition of diorganyl dichalcogenides and Oxone®. A total of 25 organoselanyl isoquinolinium imides, being 22 unprecedented in the literature, were obtained in good to excellent yields (79–95 %) in short reaction times (30–70 min) using a range of 2‐alkynyl aldehydes and diaryl, dialkyl, and diheteroaryl diselenides as substrates. The methodology was extended to tellurium, affording for the first time, tellurium isoquinolinium imides, in good yields (70–80 %) after 120 min of reaction.
Here report a one‐pot two‐steps approach to prepare organoselanyl and organotellanyl isoquinolinium imides by the 6‐endo‐dig electrophilic cyclization of N′‐(2‐alkynylbenzylidene)hydrazides using diorganyl diselenides/ditellurides and Oxone® under ultrasound irradiation.</description><subject>Aldehydes</subject><subject>Cyclization</subject><subject>Green Chemistry</subject><subject>Hydrazides</subject><subject>Imides</subject><subject>Isoquinoline</subject><subject>Selenides</subject><subject>Selenium</subject><subject>Substrates</subject><subject>Tellurium</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkEFLw0AQhRdRsFavngOeU2ezSTY5SqlaKUSogrdlm50tKeluupsgufkT_I3-ElMievQ0w-N7M49HyDWFGQWIbnFny1kEUQQUIn5CJhTyPIQ0h9Nhj1kc0py9nZML73cAkKcpnRBRGPz6-GxsG6zx0KFpK1kH69bJFrd90Nrg2WEjHQaF20pjPdbS9HUgjfpRWqxHaentoauMrStTdftgua8U-ktypmXt8epnTsnr_eJl_hiuiofl_G4VloxyHiqqkScyi5OMllrRVJXJhmmVMx6VMk9Acp4mLEaFMsYMNGSq3ADHDSjQOmVTcjPebdyQAn0rdrZzZngpIs44Y2kcxwM1G6nSWe8datG4ai9dLyiIY4niWKL4LXEw5KPhvaqx_4cWi6di_uf9BoeueTE</recordid><startdate>20221118</startdate><enddate>20221118</enddate><creator>Goulart, Helen A.</creator><creator>Araujo, Daniela R.</creator><creator>Barcellos, Angelita M.</creator><creator>Jacob, Raquel G.</creator><creator>Lenardão, Eder J.</creator><creator>Perin, Gelson</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-0359-0811</orcidid></search><sort><creationdate>20221118</creationdate><title>One‐pot Sequential Strategy to Prepare Organoselanyl and Organotellanyl Isoquinolinium Imides</title><author>Goulart, Helen A. ; Araujo, Daniela R. ; Barcellos, Angelita M. ; Jacob, Raquel G. ; Lenardão, Eder J. ; Perin, Gelson</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3177-d1fe75a84581cfd16dc5b3fd9372ca950a776534edea4e80f08dcb07eb0d0ff63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Aldehydes</topic><topic>Cyclization</topic><topic>Green Chemistry</topic><topic>Hydrazides</topic><topic>Imides</topic><topic>Isoquinoline</topic><topic>Selenides</topic><topic>Selenium</topic><topic>Substrates</topic><topic>Tellurium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goulart, Helen A.</creatorcontrib><creatorcontrib>Araujo, Daniela R.</creatorcontrib><creatorcontrib>Barcellos, Angelita M.</creatorcontrib><creatorcontrib>Jacob, Raquel G.</creatorcontrib><creatorcontrib>Lenardão, Eder J.</creatorcontrib><creatorcontrib>Perin, Gelson</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goulart, Helen A.</au><au>Araujo, Daniela R.</au><au>Barcellos, Angelita M.</au><au>Jacob, Raquel G.</au><au>Lenardão, Eder J.</au><au>Perin, Gelson</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One‐pot Sequential Strategy to Prepare Organoselanyl and Organotellanyl Isoquinolinium Imides</atitle><jtitle>European journal of organic chemistry</jtitle><date>2022-11-18</date><risdate>2022</risdate><volume>2022</volume><issue>43</issue><epage>n/a</epage><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Herein, we report an efficient, transition‐metal‐free and practical one‐pot sequential method for the synthesis of organochalcogenyl isoquinolinium imides. In this one‐pot two‐steps approach, N′‐(2‐alkynylbenzylidene) hydrazides were firstly prepared under ultrasound irradiation, followed by the addition of diorganyl dichalcogenides and Oxone®. A total of 25 organoselanyl isoquinolinium imides, being 22 unprecedented in the literature, were obtained in good to excellent yields (79–95 %) in short reaction times (30–70 min) using a range of 2‐alkynyl aldehydes and diaryl, dialkyl, and diheteroaryl diselenides as substrates. The methodology was extended to tellurium, affording for the first time, tellurium isoquinolinium imides, in good yields (70–80 %) after 120 min of reaction.
Here report a one‐pot two‐steps approach to prepare organoselanyl and organotellanyl isoquinolinium imides by the 6‐endo‐dig electrophilic cyclization of N′‐(2‐alkynylbenzylidene)hydrazides using diorganyl diselenides/ditellurides and Oxone® under ultrasound irradiation.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202201027</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-0359-0811</orcidid></addata></record> |
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subjects | Aldehydes Cyclization Green Chemistry Hydrazides Imides Isoquinoline Selenides Selenium Substrates Tellurium |
title | One‐pot Sequential Strategy to Prepare Organoselanyl and Organotellanyl Isoquinolinium Imides |
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