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Palladium-Catalyzed Amination of C-5 Bromoimidazo[2,1-b][1,3,4]thiadiazoles
A new and efficient palladium‐catalyzed amination of imidazo[2,1‐b][1,3,4]thiadiazole at the C‐5 position under microwave irradiation is reported. The reactivity toward bromine release at the C‐5 position was investigated, and palladium‐catalyzed cross‐coupling conditions were optimized. A wide rang...
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| Published in: | European Journal of Organic Chemistry 2016-04, Vol.2016 (11), p.1958-1962 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c3895-f689517a1284d0936a409fac4417896e969d81332e4f762ecbe9b8e93607964a3 |
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| cites | cdi_FETCH-LOGICAL-c3895-f689517a1284d0936a409fac4417896e969d81332e4f762ecbe9b8e93607964a3 |
| container_end_page | 1962 |
| container_issue | 11 |
| container_start_page | 1958 |
| container_title | European Journal of Organic Chemistry |
| container_volume | 2016 |
| creator | Copin, Chloé Buron, Frédéric Routier, Sylvain |
| description | A new and efficient palladium‐catalyzed amination of imidazo[2,1‐b][1,3,4]thiadiazole at the C‐5 position under microwave irradiation is reported. The reactivity toward bromine release at the C‐5 position was investigated, and palladium‐catalyzed cross‐coupling conditions were optimized. A wide range of amines was employed to examine the scope and limitations of the method. To complete this methodological study, the influence of the nature and the positions of additional imidazo[2,1‐b][1,3,4]thiadiazole substitutions was investigated.
A palladium‐catalyzed amination of imidazo[2,1‐b][1,3,4]thiadiazole at the C‐5 position under microwave irradiation is reported. A variety of amines were examined in the reaction, and the influence of imidazo[2,1‐b][1,3,4]thiadiazole substituents was investigated. |
| doi_str_mv | 10.1002/ejoc.201600145 |
| format | article |
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A palladium‐catalyzed amination of imidazo[2,1‐b][1,3,4]thiadiazole at the C‐5 position under microwave irradiation is reported. A variety of amines were examined in the reaction, and the influence of imidazo[2,1‐b][1,3,4]thiadiazole substituents was investigated.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201600145</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Amination ; Catalysis ; Chemical Sciences ; Cross-coupling ; Medicinal Chemistry ; Nitrogen heterocycles ; Organic chemistry ; Palladium ; Sulfur heterocycles</subject><ispartof>European Journal of Organic Chemistry, 2016-04, Vol.2016 (11), p.1958-1962</ispartof><rights>Copyright © 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3895-f689517a1284d0936a409fac4417896e969d81332e4f762ecbe9b8e93607964a3</citedby><cites>FETCH-LOGICAL-c3895-f689517a1284d0936a409fac4417896e969d81332e4f762ecbe9b8e93607964a3</cites><orcidid>0000-0001-5773-1515 ; 0000-0002-2823-0591</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,313,314,777,781,789,882,27903,27905,27906</link.rule.ids><backlink>$$Uhttps://hal.science/hal-04451470$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Copin, Chloé</creatorcontrib><creatorcontrib>Buron, Frédéric</creatorcontrib><creatorcontrib>Routier, Sylvain</creatorcontrib><title>Palladium-Catalyzed Amination of C-5 Bromoimidazo[2,1-b][1,3,4]thiadiazoles</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A new and efficient palladium‐catalyzed amination of imidazo[2,1‐b][1,3,4]thiadiazole at the C‐5 position under microwave irradiation is reported. The reactivity toward bromine release at the C‐5 position was investigated, and palladium‐catalyzed cross‐coupling conditions were optimized. A wide range of amines was employed to examine the scope and limitations of the method. To complete this methodological study, the influence of the nature and the positions of additional imidazo[2,1‐b][1,3,4]thiadiazole substitutions was investigated.
A palladium‐catalyzed amination of imidazo[2,1‐b][1,3,4]thiadiazole at the C‐5 position under microwave irradiation is reported. A variety of amines were examined in the reaction, and the influence of imidazo[2,1‐b][1,3,4]thiadiazole substituents was investigated.</description><subject>Amination</subject><subject>Catalysis</subject><subject>Chemical Sciences</subject><subject>Cross-coupling</subject><subject>Medicinal Chemistry</subject><subject>Nitrogen heterocycles</subject><subject>Organic chemistry</subject><subject>Palladium</subject><subject>Sulfur heterocycles</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkEFPwjAYhhejiYhePZN4MqH4de269YgTQYMCBoMJMU3ZuljcKG5Dhf_kn_CXWTJDvHlpv7TP87Z5HecUQwsDuBdqbqKWC5gBYOrtOTUMnCNgHPbtTAlFmJOnQ-eoKOYAwBnDNWcwlGkqY73KUChLma43Km60M72QpTaLhkkaIfIal7nJjM50LDdm6jYxmj1_f01xkzSpHcoXbRPsVaqKY-cgkWmhTn73uvN43RmHPdQfdG_Cdh9FJOAeSphdsS-xG9AYOGGSAk9kRCn2A84UZzwOMCGuoonPXBXNFJ8FyoLgc0YlqTvnVe6LTMUy15nM18JILXrtvtieAaUepj68Y8ueVewyN28rVZRiblb5wn5P2NdsS8x3maVaFRXlpihylexiMYhtwWJbsNgVbAVeCR86Vet_aNG5HYR_XVS5uijV586V-atgPvE9MbnviuFoPLoa3j2ICfkBj6OMYQ</recordid><startdate>201604</startdate><enddate>201604</enddate><creator>Copin, Chloé</creator><creator>Buron, Frédéric</creator><creator>Routier, Sylvain</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0001-5773-1515</orcidid><orcidid>https://orcid.org/0000-0002-2823-0591</orcidid></search><sort><creationdate>201604</creationdate><title>Palladium-Catalyzed Amination of C-5 Bromoimidazo[2,1-b][1,3,4]thiadiazoles</title><author>Copin, Chloé ; Buron, Frédéric ; Routier, Sylvain</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3895-f689517a1284d0936a409fac4417896e969d81332e4f762ecbe9b8e93607964a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Amination</topic><topic>Catalysis</topic><topic>Chemical Sciences</topic><topic>Cross-coupling</topic><topic>Medicinal Chemistry</topic><topic>Nitrogen heterocycles</topic><topic>Organic chemistry</topic><topic>Palladium</topic><topic>Sulfur heterocycles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Copin, Chloé</creatorcontrib><creatorcontrib>Buron, Frédéric</creatorcontrib><creatorcontrib>Routier, Sylvain</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Copin, Chloé</au><au>Buron, Frédéric</au><au>Routier, Sylvain</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Amination of C-5 Bromoimidazo[2,1-b][1,3,4]thiadiazoles</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2016-04</date><risdate>2016</risdate><volume>2016</volume><issue>11</issue><spage>1958</spage><epage>1962</epage><pages>1958-1962</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A new and efficient palladium‐catalyzed amination of imidazo[2,1‐b][1,3,4]thiadiazole at the C‐5 position under microwave irradiation is reported. The reactivity toward bromine release at the C‐5 position was investigated, and palladium‐catalyzed cross‐coupling conditions were optimized. A wide range of amines was employed to examine the scope and limitations of the method. To complete this methodological study, the influence of the nature and the positions of additional imidazo[2,1‐b][1,3,4]thiadiazole substitutions was investigated.
A palladium‐catalyzed amination of imidazo[2,1‐b][1,3,4]thiadiazole at the C‐5 position under microwave irradiation is reported. A variety of amines were examined in the reaction, and the influence of imidazo[2,1‐b][1,3,4]thiadiazole substituents was investigated.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201600145</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-5773-1515</orcidid><orcidid>https://orcid.org/0000-0002-2823-0591</orcidid></addata></record> |
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| identifier | ISSN: 1434-193X |
| ispartof | European Journal of Organic Chemistry, 2016-04, Vol.2016 (11), p.1958-1962 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_04451470v1 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Amination Catalysis Chemical Sciences Cross-coupling Medicinal Chemistry Nitrogen heterocycles Organic chemistry Palladium Sulfur heterocycles |
| title | Palladium-Catalyzed Amination of C-5 Bromoimidazo[2,1-b][1,3,4]thiadiazoles |
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