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Parallel synthesis of 1,2,4-triazole derivatives using microwave and continuous-flow techniques
An efficient and convenient solution-phase synthesis of a 1 H -1,2,4-triazole library with potential agrochemical activity is reported employing microwave-assisted organic synthesis (MAOS) and continuous-flow microfluidic synthetic methods starting from commercially available 3,5-dibromo-1 H -1,2,4-...
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| Published in: | Molecular diversity 2012-02, Vol.16 (1), p.81-90 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c371t-47d19447947b9920f7f66eae9443ed4e0b07a03fade78a8aa161f16c17a90ace3 |
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| cites | cdi_FETCH-LOGICAL-c371t-47d19447947b9920f7f66eae9443ed4e0b07a03fade78a8aa161f16c17a90ace3 |
| container_end_page | 90 |
| container_issue | 1 |
| container_start_page | 81 |
| container_title | Molecular diversity |
| container_volume | 16 |
| creator | Szommer, Tamás Lukács, András Kovács, József Szabó, Miklós J. Hoffmann, Michael G. Schmitt, Monika H. Gerencsér, János |
| description | An efficient and convenient solution-phase synthesis of a 1
H
-1,2,4-triazole library with potential agrochemical activity is reported employing microwave-assisted organic synthesis (MAOS) and continuous-flow microfluidic synthetic methods starting from commercially available 3,5-dibromo-1
H
-1,2,4-triazole (
1
). MAOS was used for the synthesis of 5-amino-3-bromo-1,2,4-triazole analogs
3
and for their 3-aryl derivatives
4
via Suzuki–Miyaura coupling with polymer-supported catalyst. A microfluidic hydrogenation reactor integrated into an automated parallel synthesis platform was built and utilized for the reductive dehalogenation reactions providing 5-aminotriazoles (
5
).
Graphical Abstract |
| doi_str_mv | 10.1007/s11030-012-9357-2 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_929121075</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>929121075</sourcerecordid><originalsourceid>FETCH-LOGICAL-c371t-47d19447947b9920f7f66eae9443ed4e0b07a03fade78a8aa161f16c17a90ace3</originalsourceid><addsrcrecordid>eNp1kE9P3DAQxa2qqPxpP0AvlaUeesEwY2fj-FihtiAhwYFKvVmzyQSMsg61k0Xw6fFqKaqQOHnk-b03M0-IzwhHCGCPMyIYUIBaObOwSr8Te7iwRi0A_7wvtWlQoXO4K_ZzvgUoKjQfxK7W2jY1wp7wl5RoGHiQ-SFON5xDlmMv8VAfVmpKgR7HgWXHKaxpCmvOcs4hXstVaNN4T2uWFDvZjnEKcR7nrPphvJcTtzcx_J05fxQ7PQ2ZPz2_B-L3zx9XJ6fq_OLX2cn3c9Uai5OqbIeuqqyr7NI5Db3t65qJy5_hrmJYgiUwPXVsG2qIsMYe6xYtOaCWzYH4tvW9S-Nm7uRXIbc8DBS5rOWddqgR7KKQX1-Rt-OcYlnOo7bojLGNLhRuqXJmzol7f5fCitKDR_Cb8P02fF_C95vw_Ubz5dl5Xq64e1H8S7sAegvk0orXnP4b_abrE05vj2M</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1271933782</pqid></control><display><type>article</type><title>Parallel synthesis of 1,2,4-triazole derivatives using microwave and continuous-flow techniques</title><source>Springer Nature:Jisc Collections:Springer Nature Read and Publish 2023-2025: Springer Reading List</source><creator>Szommer, Tamás ; Lukács, András ; Kovács, József ; Szabó, Miklós J. ; Hoffmann, Michael G. ; Schmitt, Monika H. ; Gerencsér, János</creator><creatorcontrib>Szommer, Tamás ; Lukács, András ; Kovács, József ; Szabó, Miklós J. ; Hoffmann, Michael G. ; Schmitt, Monika H. ; Gerencsér, János</creatorcontrib><description>An efficient and convenient solution-phase synthesis of a 1
H
-1,2,4-triazole library with potential agrochemical activity is reported employing microwave-assisted organic synthesis (MAOS) and continuous-flow microfluidic synthetic methods starting from commercially available 3,5-dibromo-1
H
-1,2,4-triazole (
1
). MAOS was used for the synthesis of 5-amino-3-bromo-1,2,4-triazole analogs
3
and for their 3-aryl derivatives
4
via Suzuki–Miyaura coupling with polymer-supported catalyst. A microfluidic hydrogenation reactor integrated into an automated parallel synthesis platform was built and utilized for the reductive dehalogenation reactions providing 5-aminotriazoles (
5
).
Graphical Abstract</description><identifier>ISSN: 1381-1991</identifier><identifier>EISSN: 1573-501X</identifier><identifier>DOI: 10.1007/s11030-012-9357-2</identifier><identifier>PMID: 22278610</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Amines - chemistry ; Biochemistry ; Biomedical and Life Sciences ; Bromides - chemistry ; Combinatorial Chemistry Techniques - methods ; Full-Length Paper ; Life Sciences ; Magnetic Resonance Spectroscopy ; Microfluidics - methods ; Microwaves ; Molecular Weight ; Organic Chemistry ; Pharmacy ; Polymer Sciences ; Rheology ; Solvents - chemistry ; Triazoles - chemical synthesis ; Triazoles - chemistry</subject><ispartof>Molecular diversity, 2012-02, Vol.16 (1), p.81-90</ispartof><rights>Springer Science+Business Media B.V. 2012</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c371t-47d19447947b9920f7f66eae9443ed4e0b07a03fade78a8aa161f16c17a90ace3</citedby><cites>FETCH-LOGICAL-c371t-47d19447947b9920f7f66eae9443ed4e0b07a03fade78a8aa161f16c17a90ace3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22278610$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Szommer, Tamás</creatorcontrib><creatorcontrib>Lukács, András</creatorcontrib><creatorcontrib>Kovács, József</creatorcontrib><creatorcontrib>Szabó, Miklós J.</creatorcontrib><creatorcontrib>Hoffmann, Michael G.</creatorcontrib><creatorcontrib>Schmitt, Monika H.</creatorcontrib><creatorcontrib>Gerencsér, János</creatorcontrib><title>Parallel synthesis of 1,2,4-triazole derivatives using microwave and continuous-flow techniques</title><title>Molecular diversity</title><addtitle>Mol Divers</addtitle><addtitle>Mol Divers</addtitle><description>An efficient and convenient solution-phase synthesis of a 1
H
-1,2,4-triazole library with potential agrochemical activity is reported employing microwave-assisted organic synthesis (MAOS) and continuous-flow microfluidic synthetic methods starting from commercially available 3,5-dibromo-1
H
-1,2,4-triazole (
1
). MAOS was used for the synthesis of 5-amino-3-bromo-1,2,4-triazole analogs
3
and for their 3-aryl derivatives
4
via Suzuki–Miyaura coupling with polymer-supported catalyst. A microfluidic hydrogenation reactor integrated into an automated parallel synthesis platform was built and utilized for the reductive dehalogenation reactions providing 5-aminotriazoles (
5
).
Graphical Abstract</description><subject>Amines - chemistry</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Bromides - chemistry</subject><subject>Combinatorial Chemistry Techniques - methods</subject><subject>Full-Length Paper</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Microfluidics - methods</subject><subject>Microwaves</subject><subject>Molecular Weight</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Polymer Sciences</subject><subject>Rheology</subject><subject>Solvents - chemistry</subject><subject>Triazoles - chemical synthesis</subject><subject>Triazoles - chemistry</subject><issn>1381-1991</issn><issn>1573-501X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp1kE9P3DAQxa2qqPxpP0AvlaUeesEwY2fj-FihtiAhwYFKvVmzyQSMsg61k0Xw6fFqKaqQOHnk-b03M0-IzwhHCGCPMyIYUIBaObOwSr8Te7iwRi0A_7wvtWlQoXO4K_ZzvgUoKjQfxK7W2jY1wp7wl5RoGHiQ-SFON5xDlmMv8VAfVmpKgR7HgWXHKaxpCmvOcs4hXstVaNN4T2uWFDvZjnEKcR7nrPphvJcTtzcx_J05fxQ7PQ2ZPz2_B-L3zx9XJ6fq_OLX2cn3c9Uai5OqbIeuqqyr7NI5Db3t65qJy5_hrmJYgiUwPXVsG2qIsMYe6xYtOaCWzYH4tvW9S-Nm7uRXIbc8DBS5rOWddqgR7KKQX1-Rt-OcYlnOo7bojLGNLhRuqXJmzol7f5fCitKDR_Cb8P02fF_C95vw_Ubz5dl5Xq64e1H8S7sAegvk0orXnP4b_abrE05vj2M</recordid><startdate>20120201</startdate><enddate>20120201</enddate><creator>Szommer, Tamás</creator><creator>Lukács, András</creator><creator>Kovács, József</creator><creator>Szabó, Miklós J.</creator><creator>Hoffmann, Michael G.</creator><creator>Schmitt, Monika H.</creator><creator>Gerencsér, János</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope></search><sort><creationdate>20120201</creationdate><title>Parallel synthesis of 1,2,4-triazole derivatives using microwave and continuous-flow techniques</title><author>Szommer, Tamás ; 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H
-1,2,4-triazole library with potential agrochemical activity is reported employing microwave-assisted organic synthesis (MAOS) and continuous-flow microfluidic synthetic methods starting from commercially available 3,5-dibromo-1
H
-1,2,4-triazole (
1
). MAOS was used for the synthesis of 5-amino-3-bromo-1,2,4-triazole analogs
3
and for their 3-aryl derivatives
4
via Suzuki–Miyaura coupling with polymer-supported catalyst. A microfluidic hydrogenation reactor integrated into an automated parallel synthesis platform was built and utilized for the reductive dehalogenation reactions providing 5-aminotriazoles (
5
).
Graphical Abstract</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><pmid>22278610</pmid><doi>10.1007/s11030-012-9357-2</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1381-1991 |
| ispartof | Molecular diversity, 2012-02, Vol.16 (1), p.81-90 |
| issn | 1381-1991 1573-501X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_929121075 |
| source | Springer Nature:Jisc Collections:Springer Nature Read and Publish 2023-2025: Springer Reading List |
| subjects | Amines - chemistry Biochemistry Biomedical and Life Sciences Bromides - chemistry Combinatorial Chemistry Techniques - methods Full-Length Paper Life Sciences Magnetic Resonance Spectroscopy Microfluidics - methods Microwaves Molecular Weight Organic Chemistry Pharmacy Polymer Sciences Rheology Solvents - chemistry Triazoles - chemical synthesis Triazoles - chemistry |
| title | Parallel synthesis of 1,2,4-triazole derivatives using microwave and continuous-flow techniques |
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