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Photochemical rearrangement of diarylethenes: synthesis of functionalized phenanthrenes
A novel protocol for the synthesis of functionalized phenanthrenes through photocyclization of diarylethenes (DAE) under UV irradiation is proposed. The reaction proceeds through 6π-electrocyclization with the formation of a cyclic (closed) intermediate that undergoes a rearrangement affording unsym...
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| Published in: | Organic & biomolecular chemistry 2020-04, Vol.18 (16), p.398-313 |
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| Main Authors: | , , , , |
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| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c363t-fb47a33e9bf8cbe47c68775ccb30fda1bdf166641a62ae59a2a2f5593da838523 |
| container_end_page | 313 |
| container_issue | 16 |
| container_start_page | 398 |
| container_title | Organic & biomolecular chemistry |
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| creator | Zakharov, A. V Yadykov, A. V Lvov, A. G Mitina, E. A Shirinian, V. Z |
| description | A novel protocol for the synthesis of functionalized phenanthrenes through photocyclization of diarylethenes (DAE) under UV irradiation is proposed. The reaction proceeds through 6π-electrocyclization with the formation of a cyclic (closed) intermediate that undergoes a rearrangement affording unsymmetrical phenanthrenes in good yields. However, in contrast to benzene derivatives, the photocyclization of naphthalene diarylethenes proceeds more slowly, which is confirmed by DFT calculations. The transformation was performed on a 1 mmol scale. The scalability showed that the diarylethenes bearing oxazole, thiazole, pyrazole and imidazole as aryl moieties are more prone to photorearrangement and can be used in preparative organic synthesis.
The photocyclization of diarylethenes bearing naphthalene units was explored and a convenient protocol for the synthesis of functionalized phenanthrenes was proposed. |
| doi_str_mv | 10.1039/d0ob00296h |
| format | article |
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The photocyclization of diarylethenes bearing naphthalene units was explored and a convenient protocol for the synthesis of functionalized phenanthrenes was proposed.</description><subject>Aromatic compounds</subject><subject>Benzene</subject><subject>Crystallography</subject><subject>Imidazole</subject><subject>Irradiation</subject><subject>Mass spectra</subject><subject>Naphthalene</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Oxazole</subject><subject>Photochemicals</subject><subject>Pyrazole</subject><subject>Ultraviolet radiation</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp90c1LwzAYBvAgipvTi3el4kWEaj6apvWm82PCYB4UjyVN39hK28ykPcy_3szNCR485YXnl5fwBKFDgi8IZullgU2OMU3jcgsNSSREiDlLtzczxQO059w7xiQVcbSLBoxSziKSDNHrU2k6o0poKiXrwIK0VrZv0EDbBUYHRSXtooauhBbcVeAWrR9d5ZaZ7lvVVaaVdfUJRTD3RvrYLuk-2tGydnCwPkfo5f7ueTwJp7OHx_H1NFQsZl2o80hIxiDNdaJyiISKEyG4UjnDupAkLzSJ4zgiMqYSeCqppJrzlBUyYQmnbITOVnvn1nz04LqsqZyCupYtmN5llCWCcpH4KyN0-oe-m9761y9VyqOEYka8Ol8pZY1zFnQ2t1XjS8gIzpZ1Z7d4dvNd98Tj4_XKPm-g2NCffj04WgHr1Cb9_S-fn_yXZ_NCsy_16pEs</recordid><startdate>20200429</startdate><enddate>20200429</enddate><creator>Zakharov, A. V</creator><creator>Yadykov, A. V</creator><creator>Lvov, A. G</creator><creator>Mitina, E. A</creator><creator>Shirinian, V. Z</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9480-3565</orcidid><orcidid>https://orcid.org/0000-0003-2951-2651</orcidid></search><sort><creationdate>20200429</creationdate><title>Photochemical rearrangement of diarylethenes: synthesis of functionalized phenanthrenes</title><author>Zakharov, A. V ; Yadykov, A. V ; Lvov, A. G ; Mitina, E. A ; Shirinian, V. Z</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-fb47a33e9bf8cbe47c68775ccb30fda1bdf166641a62ae59a2a2f5593da838523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aromatic compounds</topic><topic>Benzene</topic><topic>Crystallography</topic><topic>Imidazole</topic><topic>Irradiation</topic><topic>Mass spectra</topic><topic>Naphthalene</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Oxazole</topic><topic>Photochemicals</topic><topic>Pyrazole</topic><topic>Ultraviolet radiation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zakharov, A. V</creatorcontrib><creatorcontrib>Yadykov, A. V</creatorcontrib><creatorcontrib>Lvov, A. G</creatorcontrib><creatorcontrib>Mitina, E. A</creatorcontrib><creatorcontrib>Shirinian, V. Z</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zakharov, A. V</au><au>Yadykov, A. V</au><au>Lvov, A. G</au><au>Mitina, E. A</au><au>Shirinian, V. Z</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photochemical rearrangement of diarylethenes: synthesis of functionalized phenanthrenes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2020-04-29</date><risdate>2020</risdate><volume>18</volume><issue>16</issue><spage>398</spage><epage>313</epage><pages>398-313</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A novel protocol for the synthesis of functionalized phenanthrenes through photocyclization of diarylethenes (DAE) under UV irradiation is proposed. The reaction proceeds through 6π-electrocyclization with the formation of a cyclic (closed) intermediate that undergoes a rearrangement affording unsymmetrical phenanthrenes in good yields. However, in contrast to benzene derivatives, the photocyclization of naphthalene diarylethenes proceeds more slowly, which is confirmed by DFT calculations. The transformation was performed on a 1 mmol scale. The scalability showed that the diarylethenes bearing oxazole, thiazole, pyrazole and imidazole as aryl moieties are more prone to photorearrangement and can be used in preparative organic synthesis.
The photocyclization of diarylethenes bearing naphthalene units was explored and a convenient protocol for the synthesis of functionalized phenanthrenes was proposed.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32253418</pmid><doi>10.1039/d0ob00296h</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-9480-3565</orcidid><orcidid>https://orcid.org/0000-0003-2951-2651</orcidid></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2020-04, Vol.18 (16), p.398-313 |
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| language | eng |
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| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Aromatic compounds Benzene Crystallography Imidazole Irradiation Mass spectra Naphthalene NMR Nuclear magnetic resonance Oxazole Photochemicals Pyrazole Ultraviolet radiation |
| title | Photochemical rearrangement of diarylethenes: synthesis of functionalized phenanthrenes |
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