Synthesis of ethyl α-nitro-β-trifluoromethyl acrylate and β-trifluoromethyl-substituted tryptophan analogs and their plant growth regulating activity
Ethyl α-nitro-β-trifluoromethyl acrylate was synthesized by nucleophile-catalyzed reaction of ethyl nitroacetate with excess trifluoroacetaldehyde methyl hemiacetal and subsequent dehydration of the intermediate alcohol with P 2 O 5 . The synthesized nitro olefin regioselectively reacts with the sub...
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| Veröffentlicht in: | Russian chemical bulletin 2017-06, Vol.66 (6), p.1116-1121 |
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| container_title | Russian chemical bulletin |
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| creator | Fedorovskii, O. Yu Volkonskii, A. Yu Golubev, A. S. Spiridonov, Yu. Ya Chkanikov, N. D. |
| description | Ethyl α-nitro-β-trifluoromethyl acrylate was synthesized by nucleophile-catalyzed reaction of ethyl nitroacetate with excess trifluoroacetaldehyde methyl hemiacetal and subsequent dehydration of the intermediate alcohol with P
2
O
5
. The synthesized nitro olefin regioselectively reacts with the substituted indoles to give fluorinated 3-indolyl-2-nitrobutyrates, which were converted into the corresponding β-trifluoromethyl-substituted tryptophan analogs
via
the nitro group reduction followed by saponification of the ethoxycarbonyl group. In the step of synthesis of amino ester, the 2-methylindole derivative was resolved into diastereomers, which were transformed to the corresponding acids separately. It was found that the synthesized β-trifluoromethyltryptophans have plant-growth regulating activity apparently attributable to their metabolic transformations into substituted α-trifluoromethylindol-3-ylacetic acids. |
| doi_str_mv | 10.1007/s11172-017-1863-z |
| format | Article |
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2
O
5
. The synthesized nitro olefin regioselectively reacts with the substituted indoles to give fluorinated 3-indolyl-2-nitrobutyrates, which were converted into the corresponding β-trifluoromethyl-substituted tryptophan analogs
via
the nitro group reduction followed by saponification of the ethoxycarbonyl group. In the step of synthesis of amino ester, the 2-methylindole derivative was resolved into diastereomers, which were transformed to the corresponding acids separately. It was found that the synthesized β-trifluoromethyltryptophans have plant-growth regulating activity apparently attributable to their metabolic transformations into substituted α-trifluoromethylindol-3-ylacetic acids.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-017-1863-z</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Analogs ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Dehydration ; Fluorination ; Full Articles ; Indoles ; Inorganic Chemistry ; Organic Chemistry ; Tryptophan</subject><ispartof>Russian chemical bulletin, 2017-06, Vol.66 (6), p.1116-1121</ispartof><rights>Springer Science+Business Media, LLC 2017</rights><rights>Copyright Springer Science & Business Media 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-229a30e7d83efc1fdababa8d10f154aace603aee412f253a65d4148f81f470b13</citedby><cites>FETCH-LOGICAL-c316t-229a30e7d83efc1fdababa8d10f154aace603aee412f253a65d4148f81f470b13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11172-017-1863-z$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-017-1863-z$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Fedorovskii, O. Yu</creatorcontrib><creatorcontrib>Volkonskii, A. Yu</creatorcontrib><creatorcontrib>Golubev, A. S.</creatorcontrib><creatorcontrib>Spiridonov, Yu. Ya</creatorcontrib><creatorcontrib>Chkanikov, N. D.</creatorcontrib><title>Synthesis of ethyl α-nitro-β-trifluoromethyl acrylate and β-trifluoromethyl-substituted tryptophan analogs and their plant growth regulating activity</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><description>Ethyl α-nitro-β-trifluoromethyl acrylate was synthesized by nucleophile-catalyzed reaction of ethyl nitroacetate with excess trifluoroacetaldehyde methyl hemiacetal and subsequent dehydration of the intermediate alcohol with P
2
O
5
. The synthesized nitro olefin regioselectively reacts with the substituted indoles to give fluorinated 3-indolyl-2-nitrobutyrates, which were converted into the corresponding β-trifluoromethyl-substituted tryptophan analogs
via
the nitro group reduction followed by saponification of the ethoxycarbonyl group. In the step of synthesis of amino ester, the 2-methylindole derivative was resolved into diastereomers, which were transformed to the corresponding acids separately. It was found that the synthesized β-trifluoromethyltryptophans have plant-growth regulating activity apparently attributable to their metabolic transformations into substituted α-trifluoromethylindol-3-ylacetic acids.</description><subject>Analogs</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Dehydration</subject><subject>Fluorination</subject><subject>Full Articles</subject><subject>Indoles</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Tryptophan</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1UctKxDAULaLgOPoB7gKuo7lNH-lSBl8w4EJdh0ybtBk6TU1SpX6Jv6EfMt9kxroQRO7iXjivCyeKToGcAyH5hQOAPMYEcgwso_htL5pBmlNcQA774SZZhtOYpYfRkXNrQkjMGJtF7w9j5xvptENGIembsUXbD9xpbw3efmJvtWoHY81mwkRpx1Z4iURXob84dsPKee0HLyvk7dh70zeiC2zRmtp9q0KctqhvRedRbc2rb5CV9RBcdVeHAK9ftB-PowMlWidPfvY8erq-elzc4uX9zd3icolLCpnHcVwISmReMSpVCaoSqzCsAqIgTYQoZUaokDKBWMUpFVlaJZAwxUAlOVkBnUdnk29vzfMgnedrM9jwruNQpLTI0pATWDCxSmucs1Lx3uqNsCMHwncF8KkAHgrguwL4W9DEk8YFbldL-8v5X9EXtLaRSQ</recordid><startdate>20170601</startdate><enddate>20170601</enddate><creator>Fedorovskii, O. Yu</creator><creator>Volkonskii, A. Yu</creator><creator>Golubev, A. S.</creator><creator>Spiridonov, Yu. Ya</creator><creator>Chkanikov, N. D.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20170601</creationdate><title>Synthesis of ethyl α-nitro-β-trifluoromethyl acrylate and β-trifluoromethyl-substituted tryptophan analogs and their plant growth regulating activity</title><author>Fedorovskii, O. Yu ; Volkonskii, A. Yu ; Golubev, A. S. ; Spiridonov, Yu. Ya ; Chkanikov, N. D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-229a30e7d83efc1fdababa8d10f154aace603aee412f253a65d4148f81f470b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Analogs</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Dehydration</topic><topic>Fluorination</topic><topic>Full Articles</topic><topic>Indoles</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Tryptophan</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fedorovskii, O. Yu</creatorcontrib><creatorcontrib>Volkonskii, A. Yu</creatorcontrib><creatorcontrib>Golubev, A. S.</creatorcontrib><creatorcontrib>Spiridonov, Yu. Ya</creatorcontrib><creatorcontrib>Chkanikov, N. D.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fedorovskii, O. Yu</au><au>Volkonskii, A. Yu</au><au>Golubev, A. S.</au><au>Spiridonov, Yu. Ya</au><au>Chkanikov, N. D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of ethyl α-nitro-β-trifluoromethyl acrylate and β-trifluoromethyl-substituted tryptophan analogs and their plant growth regulating activity</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><date>2017-06-01</date><risdate>2017</risdate><volume>66</volume><issue>6</issue><spage>1116</spage><epage>1121</epage><pages>1116-1121</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>Ethyl α-nitro-β-trifluoromethyl acrylate was synthesized by nucleophile-catalyzed reaction of ethyl nitroacetate with excess trifluoroacetaldehyde methyl hemiacetal and subsequent dehydration of the intermediate alcohol with P
2
O
5
. The synthesized nitro olefin regioselectively reacts with the substituted indoles to give fluorinated 3-indolyl-2-nitrobutyrates, which were converted into the corresponding β-trifluoromethyl-substituted tryptophan analogs
via
the nitro group reduction followed by saponification of the ethoxycarbonyl group. In the step of synthesis of amino ester, the 2-methylindole derivative was resolved into diastereomers, which were transformed to the corresponding acids separately. It was found that the synthesized β-trifluoromethyltryptophans have plant-growth regulating activity apparently attributable to their metabolic transformations into substituted α-trifluoromethylindol-3-ylacetic acids.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11172-017-1863-z</doi><tpages>6</tpages></addata></record> |
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| issn | 1066-5285 1573-9171 |
| language | eng |
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| source | SpringerNature Journals |
| subjects | Analogs Chemical synthesis Chemistry Chemistry and Materials Science Chemistry/Food Science Dehydration Fluorination Full Articles Indoles Inorganic Chemistry Organic Chemistry Tryptophan |
| title | Synthesis of ethyl α-nitro-β-trifluoromethyl acrylate and β-trifluoromethyl-substituted tryptophan analogs and their plant growth regulating activity |
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