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A facile approach to hybrid compounds containing a tricyclic diterpenoid and fluorine-substituted heterocycles
[Display omitted] •A selective methodology for the introduction of fluorinated heterocycles in diterpenic acid core.•Regioselective synthesis of a series of fluorinated benzofuran and benzopyrane derivatives.•A convenient synthetic route to fluorinated analogs and derivatives of natural compounds. 2...
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| Published in: | Journal of fluorine chemistry 2020-08, Vol.236, p.109554, Article 109554 |
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| Main Authors: | , , , , |
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| cites | cdi_FETCH-LOGICAL-c340t-3d3a0aced1d8ad5e2ff9e78e1703761189aebcf395c4d9d20a02c95ec8b4ec673 |
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| container_start_page | 109554 |
| container_title | Journal of fluorine chemistry |
| container_volume | 236 |
| creator | Gromova, M.A. Kharitonov, Yu.V. Politanskaya, L.V. Tretyakov, E.V. Shults, E.E. |
| description | [Display omitted]
•A selective methodology for the introduction of fluorinated heterocycles in diterpenic acid core.•Regioselective synthesis of a series of fluorinated benzofuran and benzopyrane derivatives.•A convenient synthetic route to fluorinated analogs and derivatives of natural compounds.
2,3-Butadienes have become valuable building blocks in the synthesis of various heterocyclic compounds. The Pd-catalyzed cross-coupling and cyclization reaction of N-(2,3-butadienyl)carboxamide of isopimaric acid with fluorine-substituted 2-iodophenols proceeds with the formation of optically active fluorinated benzofuran and benzopyrane derivatives of isopimaric acid. This transformation opens a potential route to the synthesis of hybrid compounds containing a tricyclic diterpenoid moiety and several fluorinated benzoannelated heterocycles. |
| doi_str_mv | 10.1016/j.jfluchem.2020.109554 |
| format | article |
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•A selective methodology for the introduction of fluorinated heterocycles in diterpenic acid core.•Regioselective synthesis of a series of fluorinated benzofuran and benzopyrane derivatives.•A convenient synthetic route to fluorinated analogs and derivatives of natural compounds.
2,3-Butadienes have become valuable building blocks in the synthesis of various heterocyclic compounds. The Pd-catalyzed cross-coupling and cyclization reaction of N-(2,3-butadienyl)carboxamide of isopimaric acid with fluorine-substituted 2-iodophenols proceeds with the formation of optically active fluorinated benzofuran and benzopyrane derivatives of isopimaric acid. This transformation opens a potential route to the synthesis of hybrid compounds containing a tricyclic diterpenoid moiety and several fluorinated benzoannelated heterocycles.</description><identifier>ISSN: 0022-1139</identifier><identifier>EISSN: 1873-3328</identifier><identifier>DOI: 10.1016/j.jfluchem.2020.109554</identifier><language>eng</language><publisher>Lausanne: Elsevier B.V</publisher><subject>2Н-chromenes ; Benzofuran ; Benzofurans ; Coupling (molecular) ; Cross coupling ; Cross-coupling-cyclization ; Diterpenes ; Fluorinated heterocycles ; Fluorination ; Fluorine ; Heterocyclic compounds ; Isopimaric acid ; Optical activity ; Substitutes ; Terpenoid allene</subject><ispartof>Journal of fluorine chemistry, 2020-08, Vol.236, p.109554, Article 109554</ispartof><rights>2020</rights><rights>Copyright Elsevier BV Aug 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c340t-3d3a0aced1d8ad5e2ff9e78e1703761189aebcf395c4d9d20a02c95ec8b4ec673</citedby><cites>FETCH-LOGICAL-c340t-3d3a0aced1d8ad5e2ff9e78e1703761189aebcf395c4d9d20a02c95ec8b4ec673</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Gromova, M.A.</creatorcontrib><creatorcontrib>Kharitonov, Yu.V.</creatorcontrib><creatorcontrib>Politanskaya, L.V.</creatorcontrib><creatorcontrib>Tretyakov, E.V.</creatorcontrib><creatorcontrib>Shults, E.E.</creatorcontrib><title>A facile approach to hybrid compounds containing a tricyclic diterpenoid and fluorine-substituted heterocycles</title><title>Journal of fluorine chemistry</title><description>[Display omitted]
•A selective methodology for the introduction of fluorinated heterocycles in diterpenic acid core.•Regioselective synthesis of a series of fluorinated benzofuran and benzopyrane derivatives.•A convenient synthetic route to fluorinated analogs and derivatives of natural compounds.
2,3-Butadienes have become valuable building blocks in the synthesis of various heterocyclic compounds. The Pd-catalyzed cross-coupling and cyclization reaction of N-(2,3-butadienyl)carboxamide of isopimaric acid with fluorine-substituted 2-iodophenols proceeds with the formation of optically active fluorinated benzofuran and benzopyrane derivatives of isopimaric acid. This transformation opens a potential route to the synthesis of hybrid compounds containing a tricyclic diterpenoid moiety and several fluorinated benzoannelated heterocycles.</description><subject>2Н-chromenes</subject><subject>Benzofuran</subject><subject>Benzofurans</subject><subject>Coupling (molecular)</subject><subject>Cross coupling</subject><subject>Cross-coupling-cyclization</subject><subject>Diterpenes</subject><subject>Fluorinated heterocycles</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Heterocyclic compounds</subject><subject>Isopimaric acid</subject><subject>Optical activity</subject><subject>Substitutes</subject><subject>Terpenoid allene</subject><issn>0022-1139</issn><issn>1873-3328</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFUMtKBDEQDKLg-vgFCXieNY95ZG6K-ALBi55DttPjZthNxiQj7N-bZfXsqZumqrqqCLnibMkZb2_G5ThsZljjdimY2B_7pqmPyIKrTlZSCnVMFowJUXEu-1NyltLIGOtYpxbE39HBgNsgNdMUg4E1zYGud6voLIWwncLsbSqbz8Z55z-poTk62MHGAbUuY5zQhwI23tLiI0TnsUrzKmWX54yWrrGAwp6B6YKcDGaT8PJ3npOPx4f3--fq9e3p5f7utQJZs1xJKw0zgJZbZWyDYhh67BTyjsmu5Vz1BlcwyL6B2vZWMMME9A2CWtUIbSfPyfVBt2T6mjFlPYY5-vJSi7ppVafqVhZUe0BBDClFHPQU3dbEneZM77vVo_7rVu-71YduC_H2QMSS4dth1Akc-mLYRYSsbXD_SfwA3k6JEQ</recordid><startdate>202008</startdate><enddate>202008</enddate><creator>Gromova, M.A.</creator><creator>Kharitonov, Yu.V.</creator><creator>Politanskaya, L.V.</creator><creator>Tretyakov, E.V.</creator><creator>Shults, E.E.</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>7U7</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope></search><sort><creationdate>202008</creationdate><title>A facile approach to hybrid compounds containing a tricyclic diterpenoid and fluorine-substituted heterocycles</title><author>Gromova, M.A. ; Kharitonov, Yu.V. ; Politanskaya, L.V. ; Tretyakov, E.V. ; Shults, E.E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c340t-3d3a0aced1d8ad5e2ff9e78e1703761189aebcf395c4d9d20a02c95ec8b4ec673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>2Н-chromenes</topic><topic>Benzofuran</topic><topic>Benzofurans</topic><topic>Coupling (molecular)</topic><topic>Cross coupling</topic><topic>Cross-coupling-cyclization</topic><topic>Diterpenes</topic><topic>Fluorinated heterocycles</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Heterocyclic compounds</topic><topic>Isopimaric acid</topic><topic>Optical activity</topic><topic>Substitutes</topic><topic>Terpenoid allene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gromova, M.A.</creatorcontrib><creatorcontrib>Kharitonov, Yu.V.</creatorcontrib><creatorcontrib>Politanskaya, L.V.</creatorcontrib><creatorcontrib>Tretyakov, E.V.</creatorcontrib><creatorcontrib>Shults, E.E.</creatorcontrib><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of fluorine chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gromova, M.A.</au><au>Kharitonov, Yu.V.</au><au>Politanskaya, L.V.</au><au>Tretyakov, E.V.</au><au>Shults, E.E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A facile approach to hybrid compounds containing a tricyclic diterpenoid and fluorine-substituted heterocycles</atitle><jtitle>Journal of fluorine chemistry</jtitle><date>2020-08</date><risdate>2020</risdate><volume>236</volume><spage>109554</spage><pages>109554-</pages><artnum>109554</artnum><issn>0022-1139</issn><eissn>1873-3328</eissn><abstract>[Display omitted]
•A selective methodology for the introduction of fluorinated heterocycles in diterpenic acid core.•Regioselective synthesis of a series of fluorinated benzofuran and benzopyrane derivatives.•A convenient synthetic route to fluorinated analogs and derivatives of natural compounds.
2,3-Butadienes have become valuable building blocks in the synthesis of various heterocyclic compounds. The Pd-catalyzed cross-coupling and cyclization reaction of N-(2,3-butadienyl)carboxamide of isopimaric acid with fluorine-substituted 2-iodophenols proceeds with the formation of optically active fluorinated benzofuran and benzopyrane derivatives of isopimaric acid. This transformation opens a potential route to the synthesis of hybrid compounds containing a tricyclic diterpenoid moiety and several fluorinated benzoannelated heterocycles.</abstract><cop>Lausanne</cop><pub>Elsevier B.V</pub><doi>10.1016/j.jfluchem.2020.109554</doi></addata></record> |
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| ispartof | Journal of fluorine chemistry, 2020-08, Vol.236, p.109554, Article 109554 |
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| language | eng |
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| source | ScienceDirect Journals |
| subjects | 2Н-chromenes Benzofuran Benzofurans Coupling (molecular) Cross coupling Cross-coupling-cyclization Diterpenes Fluorinated heterocycles Fluorination Fluorine Heterocyclic compounds Isopimaric acid Optical activity Substitutes Terpenoid allene |
| title | A facile approach to hybrid compounds containing a tricyclic diterpenoid and fluorine-substituted heterocycles |
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