2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features
An efficient one-pot method was developed for the synthesis of 2-(1,2,4-oxadiazol-5-yl)anilines via the reaction of amidoximes with isatoic anhydrides in a NaOH–DMSO medium at ambient temperature. The method allows to obtain structurally diverse substituted anilines bearing the 1,2,4-oxadiazole moti...
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| Veröffentlicht in: | Russian journal of general chemistry 2021-05, Vol.91 (5), p.768-778 |
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| container_title | Russian journal of general chemistry |
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| creator | Tarasenko, M. V. Kotlyarova, V. D. Baykov, S. V. Shetnev, A. A. |
| description | An efficient one-pot method was developed for the synthesis of 2-(1,2,4-oxadiazol-5-yl)anilines via the reaction of amidoximes with isatoic anhydrides in a NaOH–DMSO medium at ambient temperature. The method allows to obtain structurally diverse substituted anilines bearing the 1,2,4-oxadiazole motif in moderate to excellent yields without the utilization of protective groups. The reaction scope includes aryl, hetaryl, and cycloalkyl amidoxime and isatoic anhydrides with different substituents in the aromatic ring as well as at the amide N atom. Structures of two anilines were studied by single crystal X-ray diffraction method and intramolecular hydrogen bonding between N atom of oxadiazole moiety and NH
2
group was revealed. |
| doi_str_mv | 10.1134/S1070363221050030 |
| format | Article |
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group was revealed.</description><identifier>ISSN: 1070-3632</identifier><identifier>EISSN: 1608-3350</identifier><identifier>DOI: 10.1134/S1070363221050030</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Ambient temperature ; Anhydrides ; Aniline ; Aromatic compounds ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Crystal structure ; Diffraction ; Hydrogen ; Hydrogen bonding ; Oxadiazoles ; Single crystals ; X-rays</subject><ispartof>Russian journal of general chemistry, 2021-05, Vol.91 (5), p.768-778</ispartof><rights>Pleiades Publishing, Ltd. 2021</rights><rights>COPYRIGHT 2021 Springer</rights><rights>Pleiades Publishing, Ltd. 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c285t-3b892749197d09e8bdc35ab2ffe17be29035fcd47072a8a4a5c1d8848e4bf4cb3</citedby><cites>FETCH-LOGICAL-c285t-3b892749197d09e8bdc35ab2ffe17be29035fcd47072a8a4a5c1d8848e4bf4cb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070363221050030$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070363221050030$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Tarasenko, M. V.</creatorcontrib><creatorcontrib>Kotlyarova, V. D.</creatorcontrib><creatorcontrib>Baykov, S. V.</creatorcontrib><creatorcontrib>Shetnev, A. A.</creatorcontrib><title>2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features</title><title>Russian journal of general chemistry</title><addtitle>Russ J Gen Chem</addtitle><description>An efficient one-pot method was developed for the synthesis of 2-(1,2,4-oxadiazol-5-yl)anilines via the reaction of amidoximes with isatoic anhydrides in a NaOH–DMSO medium at ambient temperature. The method allows to obtain structurally diverse substituted anilines bearing the 1,2,4-oxadiazole motif in moderate to excellent yields without the utilization of protective groups. The reaction scope includes aryl, hetaryl, and cycloalkyl amidoxime and isatoic anhydrides with different substituents in the aromatic ring as well as at the amide N atom. Structures of two anilines were studied by single crystal X-ray diffraction method and intramolecular hydrogen bonding between N atom of oxadiazole moiety and NH
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group was revealed.</description><subject>Ambient temperature</subject><subject>Anhydrides</subject><subject>Aniline</subject><subject>Aromatic compounds</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Crystal structure</subject><subject>Diffraction</subject><subject>Hydrogen</subject><subject>Hydrogen bonding</subject><subject>Oxadiazoles</subject><subject>Single crystals</subject><subject>X-rays</subject><issn>1070-3632</issn><issn>1608-3350</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp1kU1rHDEMhofSQNOkP6C3gVxSiBPJHzue3rah-YBADtueB4-tSRxm7MSehWx_fb1MoIcSdJDQ-z6SQFX1FeEcUciLDUIDYiU4R1AAAj5Uh7gCzYRQ8LHURWZ7_VP1OecnAARY8cNq4uwUz_iZZPevxnnzJ45Msd34zQQ_-kC5_mEyuTqGej15F1_9VHomuPo2mzl6W6_D484l7yh_rze7MD9S9otjM6etnbeJ6isy-5yPq4PBjJm-vOWj6vfVz1-XN-zu_vr2cn3HLNdqZqLXLW9ki23joCXdOyuU6fkwEDY98RaEGqyTDTTcaCONsui0lppkP0jbi6PqZJn7nOLLlvLcPcVtCmVlx5XkQiM2qrjOF9eDGanzYYhzMraEo8nbGGjwpb9uUAvdqhUWABfApphzoqF7Tn4yadchdPs3dP-9oTB8YXLxhgdK_055H_oL5veHrw</recordid><startdate>20210501</startdate><enddate>20210501</enddate><creator>Tarasenko, M. V.</creator><creator>Kotlyarova, V. D.</creator><creator>Baykov, S. V.</creator><creator>Shetnev, A. A.</creator><general>Pleiades Publishing</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20210501</creationdate><title>2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features</title><author>Tarasenko, M. V. ; Kotlyarova, V. D. ; Baykov, S. V. ; Shetnev, A. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c285t-3b892749197d09e8bdc35ab2ffe17be29035fcd47072a8a4a5c1d8848e4bf4cb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Ambient temperature</topic><topic>Anhydrides</topic><topic>Aniline</topic><topic>Aromatic compounds</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Crystal structure</topic><topic>Diffraction</topic><topic>Hydrogen</topic><topic>Hydrogen bonding</topic><topic>Oxadiazoles</topic><topic>Single crystals</topic><topic>X-rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tarasenko, M. V.</creatorcontrib><creatorcontrib>Kotlyarova, V. D.</creatorcontrib><creatorcontrib>Baykov, S. V.</creatorcontrib><creatorcontrib>Shetnev, A. A.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of general chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tarasenko, M. V.</au><au>Kotlyarova, V. D.</au><au>Baykov, S. V.</au><au>Shetnev, A. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features</atitle><jtitle>Russian journal of general chemistry</jtitle><stitle>Russ J Gen Chem</stitle><date>2021-05-01</date><risdate>2021</risdate><volume>91</volume><issue>5</issue><spage>768</spage><epage>778</epage><pages>768-778</pages><issn>1070-3632</issn><eissn>1608-3350</eissn><abstract>An efficient one-pot method was developed for the synthesis of 2-(1,2,4-oxadiazol-5-yl)anilines via the reaction of amidoximes with isatoic anhydrides in a NaOH–DMSO medium at ambient temperature. The method allows to obtain structurally diverse substituted anilines bearing the 1,2,4-oxadiazole motif in moderate to excellent yields without the utilization of protective groups. The reaction scope includes aryl, hetaryl, and cycloalkyl amidoxime and isatoic anhydrides with different substituents in the aromatic ring as well as at the amide N atom. Structures of two anilines were studied by single crystal X-ray diffraction method and intramolecular hydrogen bonding between N atom of oxadiazole moiety and NH
2
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| subjects | Ambient temperature Anhydrides Aniline Aromatic compounds Chemistry Chemistry and Materials Science Chemistry/Food Science Crystal structure Diffraction Hydrogen Hydrogen bonding Oxadiazoles Single crystals X-rays |
| title | 2-(1,2,4-Oxadiazol-5-yl)anilines Based on Amidoximes and Isatoic Anhydrides: Synthesis and Structure Features |
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