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Design, synthesis, and structure of alkyl 1H-pyrazolecarboxylates from a raspberry ketone methyl ether
This paper reports a one-pot synthesis of 5-[2-(4-methoxyphenyl)ethyl]-1 H -pyrazole-3-carboxylates via cyclocondensation of 1,1,1-trichloro-4-methoxy-6-(4-methoxyphenyl)hex-3-en-2-one with hydrazine hydrochloride in ROH (R = Me, Et, n -Pr, i -Pr, i -Bu, i -Am, hexadecyl) under conventional and micr...
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| Published in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-10, Vol.56 (10), p.1314-1320 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c291t-a99a3acc9bbfe01ec1c28787cf4e102e3cd340205f9637d447fb7f76fb11bdaf3 |
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| cites | cdi_FETCH-LOGICAL-c291t-a99a3acc9bbfe01ec1c28787cf4e102e3cd340205f9637d447fb7f76fb11bdaf3 |
| container_end_page | 1320 |
| container_issue | 10 |
| container_start_page | 1314 |
| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
| container_volume | 56 |
| creator | Goulart, Taís B. Neves, Adriana M. Soares, Mayara S. P. Stefanello, Francieli M. Campos, Patrick T. Moura, Sidnei Cargnelutti, Roberta Flores, Alex F. C. |
| description | This paper reports a one-pot synthesis of 5-[2-(4-methoxyphenyl)ethyl]-1
H
-pyrazole-3-carboxylates
via
cyclocondensation of 1,1,1-trichloro-4-methoxy-6-(4-methoxyphenyl)hex-3-en-2-one with hydrazine hydrochloride in ROH (R = Me, Et,
n
-Pr,
i
-Pr,
i
-Bu,
i
-Am, hexadecyl) under conventional and microwave heating. Yields are comparable in both methods, but under MW heating the reaction proceeds faster. The antioxidant activity of the compounds was measured using DPPH radical scavenging assay. It was observed, that the increase of the alcohol chain length decreases the antioxidant potential of the raspberry ketone derived molecular system. |
| doi_str_mv | 10.1007/s10593-020-02816-z |
| format | article |
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H
-pyrazole-3-carboxylates
via
cyclocondensation of 1,1,1-trichloro-4-methoxy-6-(4-methoxyphenyl)hex-3-en-2-one with hydrazine hydrochloride in ROH (R = Me, Et,
n
-Pr,
i
-Pr,
i
-Bu,
i
-Am, hexadecyl) under conventional and microwave heating. Yields are comparable in both methods, but under MW heating the reaction proceeds faster. The antioxidant activity of the compounds was measured using DPPH radical scavenging assay. It was observed, that the increase of the alcohol chain length decreases the antioxidant potential of the raspberry ketone derived molecular system.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/s10593-020-02816-z</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Chemistry ; Chemistry and Materials Science ; Organic Chemistry ; Pharmacy</subject><ispartof>Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2020-10, Vol.56 (10), p.1314-1320</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c291t-a99a3acc9bbfe01ec1c28787cf4e102e3cd340205f9637d447fb7f76fb11bdaf3</citedby><cites>FETCH-LOGICAL-c291t-a99a3acc9bbfe01ec1c28787cf4e102e3cd340205f9637d447fb7f76fb11bdaf3</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></links><search><creatorcontrib>Goulart, Taís B.</creatorcontrib><creatorcontrib>Neves, Adriana M.</creatorcontrib><creatorcontrib>Soares, Mayara S. P.</creatorcontrib><creatorcontrib>Stefanello, Francieli M.</creatorcontrib><creatorcontrib>Campos, Patrick T.</creatorcontrib><creatorcontrib>Moura, Sidnei</creatorcontrib><creatorcontrib>Cargnelutti, Roberta</creatorcontrib><creatorcontrib>Flores, Alex F. C.</creatorcontrib><title>Design, synthesis, and structure of alkyl 1H-pyrazolecarboxylates from a raspberry ketone methyl ether</title><title>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</title><addtitle>Chem Heterocycl Comp</addtitle><description>This paper reports a one-pot synthesis of 5-[2-(4-methoxyphenyl)ethyl]-1
H
-pyrazole-3-carboxylates
via
cyclocondensation of 1,1,1-trichloro-4-methoxy-6-(4-methoxyphenyl)hex-3-en-2-one with hydrazine hydrochloride in ROH (R = Me, Et,
n
-Pr,
i
-Pr,
i
-Bu,
i
-Am, hexadecyl) under conventional and microwave heating. Yields are comparable in both methods, but under MW heating the reaction proceeds faster. The antioxidant activity of the compounds was measured using DPPH radical scavenging assay. It was observed, that the increase of the alcohol chain length decreases the antioxidant potential of the raspberry ketone derived molecular system.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kMtOwzAQRS0EEqXwA6z8ATV44qROlqhAi1SJDawtxxn3lSbV2JVIvx5DWbOYlzTnauYydg_yAaTUjwFkUSkhM5mihKk4XbARFFqJUhXqko2klJVQkGXX7CaEbRo1lPmI-WcMm1U34WHo4jr1YcJt1_AQ6ejikZD3ntt2N7QcFuIwkD31LTpLdf81tDZi4J76PbecbDjUSDTwHca-Q77HuE5Yyki37MrbNuDdXx2zz9eXj9lCLN_nb7OnpXBZBVHYqrLKOlfVtUcJ6MBlpS618zmCzFC5RuXpycJXU6WbPNe-1l5PfQ1QN9arMcvOuo76EAi9OdBmb2kwIM2PU-bslEki5tcpc0qQOkMhLXcrJLPtj9SlO_-jvgHe9295</recordid><startdate>20201001</startdate><enddate>20201001</enddate><creator>Goulart, Taís B.</creator><creator>Neves, Adriana M.</creator><creator>Soares, Mayara S. P.</creator><creator>Stefanello, Francieli M.</creator><creator>Campos, Patrick T.</creator><creator>Moura, Sidnei</creator><creator>Cargnelutti, Roberta</creator><creator>Flores, Alex F. C.</creator><general>Springer US</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20201001</creationdate><title>Design, synthesis, and structure of alkyl 1H-pyrazolecarboxylates from a raspberry ketone methyl ether</title><author>Goulart, Taís B. ; Neves, Adriana M. ; Soares, Mayara S. P. ; Stefanello, Francieli M. ; Campos, Patrick T. ; Moura, Sidnei ; Cargnelutti, Roberta ; Flores, Alex F. C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c291t-a99a3acc9bbfe01ec1c28787cf4e102e3cd340205f9637d447fb7f76fb11bdaf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goulart, Taís B.</creatorcontrib><creatorcontrib>Neves, Adriana M.</creatorcontrib><creatorcontrib>Soares, Mayara S. P.</creatorcontrib><creatorcontrib>Stefanello, Francieli M.</creatorcontrib><creatorcontrib>Campos, Patrick T.</creatorcontrib><creatorcontrib>Moura, Sidnei</creatorcontrib><creatorcontrib>Cargnelutti, Roberta</creatorcontrib><creatorcontrib>Flores, Alex F. C.</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goulart, Taís B.</au><au>Neves, Adriana M.</au><au>Soares, Mayara S. P.</au><au>Stefanello, Francieli M.</au><au>Campos, Patrick T.</au><au>Moura, Sidnei</au><au>Cargnelutti, Roberta</au><au>Flores, Alex F. C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis, and structure of alkyl 1H-pyrazolecarboxylates from a raspberry ketone methyl ether</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2020-10-01</date><risdate>2020</risdate><volume>56</volume><issue>10</issue><spage>1314</spage><epage>1320</epage><pages>1314-1320</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>This paper reports a one-pot synthesis of 5-[2-(4-methoxyphenyl)ethyl]-1
H
-pyrazole-3-carboxylates
via
cyclocondensation of 1,1,1-trichloro-4-methoxy-6-(4-methoxyphenyl)hex-3-en-2-one with hydrazine hydrochloride in ROH (R = Me, Et,
n
-Pr,
i
-Pr,
i
-Bu,
i
-Am, hexadecyl) under conventional and microwave heating. Yields are comparable in both methods, but under MW heating the reaction proceeds faster. The antioxidant activity of the compounds was measured using DPPH radical scavenging assay. It was observed, that the increase of the alcohol chain length decreases the antioxidant potential of the raspberry ketone derived molecular system.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10593-020-02816-z</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 0009-3122 |
| ispartof | Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2020-10, Vol.56 (10), p.1314-1320 |
| issn | 0009-3122 1573-8353 |
| language | eng |
| recordid | cdi_crossref_primary_10_1007_s10593_020_02816_z |
| source | Springer Nature |
| subjects | Chemistry Chemistry and Materials Science Organic Chemistry Pharmacy |
| title | Design, synthesis, and structure of alkyl 1H-pyrazolecarboxylates from a raspberry ketone methyl ether |
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