Construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes by photocycloaddition reaction of 1,4-dihydropyridines: Experimental and theoretical investigation
A photocycloaddition reaction of ethyl 1,4-diaryl-1,4-dihydropyridine-3-carboxylate for the construction of 3,9-diazatetraasteranes (P1) and 3,9-diazatetracyclododecanes (P2) is reported for the first time. The types of reaction product clearly differ with solvent, regardless of the irradiation wave...
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| Veröffentlicht in: | Chinese chemical letters 2023-12, Vol.34 (12), p.108183-182, Article 108183 |
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| creator | Sun, Runzhi Song, Xiuqing Wang, Shijie Zhang, Xiaokun Yan, Hong Wang, Yeming |
| description | A photocycloaddition reaction of ethyl 1,4-diaryl-1,4-dihydropyridine-3-carboxylate for the construction of 3,9-diazatetraasteranes (P1) and 3,9-diazatetracyclododecanes (P2) is reported for the first time. The types of reaction product clearly differ with solvent, regardless of the irradiation wavelength. The difference in P1 and P2 lies in the second step of the intramolecular [2 + 2] photocyclization. In order to further investigate this phenomenon and gain a deeper understanding of the photochemical behavior of 1,4-dihydropyridines, DFT and TDDFT theoretical calculations are performed. The results provide a good explanation for the formation of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes.
A photocycloaddition reaction of ethyl 1,4-diaryl-1,4-dihydropyridine-3-carboxylate for the construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes is reported for the first time. In order to further investigate this phenomenon and gain a deeper understanding of the photochemical behavior of 1,4-dihydropyridines, DFT and TDDFT theoretical calculations were performed. The results provide a good explanation for the formation of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes. [Display omitted] |
| doi_str_mv | 10.1016/j.cclet.2023.108183 |
| format | Article |
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A photocycloaddition reaction of ethyl 1,4-diaryl-1,4-dihydropyridine-3-carboxylate for the construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes is reported for the first time. In order to further investigate this phenomenon and gain a deeper understanding of the photochemical behavior of 1,4-dihydropyridines, DFT and TDDFT theoretical calculations were performed. The results provide a good explanation for the formation of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes. [Display omitted]</description><identifier>ISSN: 1001-8417</identifier><identifier>DOI: 10.1016/j.cclet.2023.108183</identifier><language>eng</language><publisher>Elsevier B.V</publisher><subject>1,4-Dihydropyridine ; 3,9-Diazatetracyclododecanes ; Photocycloaddition ; Theoretical investigation</subject><ispartof>Chinese chemical letters, 2023-12, Vol.34 (12), p.108183-182, Article 108183</ispartof><rights>2023</rights><rights>Copyright © Wanfang Data Co. Ltd. All Rights Reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c335t-19213cd719d418e1d3a39350a638c7ce7429deba7e564b50ebab0942e9713e3a3</citedby><cites>FETCH-LOGICAL-c335t-19213cd719d418e1d3a39350a638c7ce7429deba7e564b50ebab0942e9713e3a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Uhttp://www.wanfangdata.com.cn/images/PeriodicalImages/zghxkb/zghxkb.jpg</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Sun, Runzhi</creatorcontrib><creatorcontrib>Song, Xiuqing</creatorcontrib><creatorcontrib>Wang, Shijie</creatorcontrib><creatorcontrib>Zhang, Xiaokun</creatorcontrib><creatorcontrib>Yan, Hong</creatorcontrib><creatorcontrib>Wang, Yeming</creatorcontrib><title>Construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes by photocycloaddition reaction of 1,4-dihydropyridines: Experimental and theoretical investigation</title><title>Chinese chemical letters</title><description>A photocycloaddition reaction of ethyl 1,4-diaryl-1,4-dihydropyridine-3-carboxylate for the construction of 3,9-diazatetraasteranes (P1) and 3,9-diazatetracyclododecanes (P2) is reported for the first time. The types of reaction product clearly differ with solvent, regardless of the irradiation wavelength. The difference in P1 and P2 lies in the second step of the intramolecular [2 + 2] photocyclization. In order to further investigate this phenomenon and gain a deeper understanding of the photochemical behavior of 1,4-dihydropyridines, DFT and TDDFT theoretical calculations are performed. The results provide a good explanation for the formation of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes.
A photocycloaddition reaction of ethyl 1,4-diaryl-1,4-dihydropyridine-3-carboxylate for the construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes is reported for the first time. In order to further investigate this phenomenon and gain a deeper understanding of the photochemical behavior of 1,4-dihydropyridines, DFT and TDDFT theoretical calculations were performed. The results provide a good explanation for the formation of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes. [Display omitted]</description><subject>1,4-Dihydropyridine</subject><subject>3,9-Diazatetracyclododecanes</subject><subject>Photocycloaddition</subject><subject>Theoretical investigation</subject><issn>1001-8417</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kbtOwzAUhjOARCk8AUs2lqbYcZoLEgOqykWqxAKzdWKftC7Frmy3NH0lXhI3QQwMLL4c_99_dPxH0RUlY0pofrMaC7FGP05JykKlpCU7iQaUEJqUGS3OonPnVoSkZcnyQfQ1Ndp5uxVeGR2bJmajKpEKDuDRWwDn0YJGF4OWf95EK9ZGGomiE9RtvFkab7oySKk6R4vwa01HWcCXrbRm01olVcBu49l-g1Z9oPaw7rr4JRqLXolwV3qHzqsFHD0uotMG1g4vf_Zh9PYwe50-JfOXx-fp_TwRjE18QquUMiELWsmMlkglA1axCYGclaIQWGRpJbGGAid5Vk9IONakylKsCsowiIfRde_7CboBveArs7U6dOSHxXL_Xh9_loYlC0rWK4U1zlls-CaMArbllPBjGnzFuzT4keF9GoG66ykMQ-wUWu6EQi1QKovCc2nUv_w3bQianQ</recordid><startdate>20231201</startdate><enddate>20231201</enddate><creator>Sun, Runzhi</creator><creator>Song, Xiuqing</creator><creator>Wang, Shijie</creator><creator>Zhang, Xiaokun</creator><creator>Yan, Hong</creator><creator>Wang, Yeming</creator><general>Elsevier B.V</general><general>Faculty of Environment and Life,Beijing University of Technology,Beijing 100124,China%Large-scale Instruments and Equipments Sharing Platform,Beijing University of Technology,Beijing 100124,China%Beijing Tide Pharmaceutical Co.,Ltd.,Beijing 100176,China</general><scope>AAYXX</scope><scope>CITATION</scope><scope>2B.</scope><scope>4A8</scope><scope>92I</scope><scope>93N</scope><scope>PSX</scope><scope>TCJ</scope></search><sort><creationdate>20231201</creationdate><title>Construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes by photocycloaddition reaction of 1,4-dihydropyridines: Experimental and theoretical investigation</title><author>Sun, Runzhi ; Song, Xiuqing ; Wang, Shijie ; Zhang, Xiaokun ; Yan, Hong ; Wang, Yeming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c335t-19213cd719d418e1d3a39350a638c7ce7429deba7e564b50ebab0942e9713e3a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>1,4-Dihydropyridine</topic><topic>3,9-Diazatetracyclododecanes</topic><topic>Photocycloaddition</topic><topic>Theoretical investigation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Runzhi</creatorcontrib><creatorcontrib>Song, Xiuqing</creatorcontrib><creatorcontrib>Wang, Shijie</creatorcontrib><creatorcontrib>Zhang, Xiaokun</creatorcontrib><creatorcontrib>Yan, Hong</creatorcontrib><creatorcontrib>Wang, Yeming</creatorcontrib><collection>CrossRef</collection><collection>Wanfang Data Journals - Hong Kong</collection><collection>WANFANG Data Centre</collection><collection>Wanfang Data Journals</collection><collection>万方数据期刊 - 香港版</collection><collection>China Online Journals (COJ)</collection><collection>China Online Journals (COJ)</collection><jtitle>Chinese chemical letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Runzhi</au><au>Song, Xiuqing</au><au>Wang, Shijie</au><au>Zhang, Xiaokun</au><au>Yan, Hong</au><au>Wang, Yeming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes by photocycloaddition reaction of 1,4-dihydropyridines: Experimental and theoretical investigation</atitle><jtitle>Chinese chemical letters</jtitle><date>2023-12-01</date><risdate>2023</risdate><volume>34</volume><issue>12</issue><spage>108183</spage><epage>182</epage><pages>108183-182</pages><artnum>108183</artnum><issn>1001-8417</issn><abstract>A photocycloaddition reaction of ethyl 1,4-diaryl-1,4-dihydropyridine-3-carboxylate for the construction of 3,9-diazatetraasteranes (P1) and 3,9-diazatetracyclododecanes (P2) is reported for the first time. The types of reaction product clearly differ with solvent, regardless of the irradiation wavelength. The difference in P1 and P2 lies in the second step of the intramolecular [2 + 2] photocyclization. In order to further investigate this phenomenon and gain a deeper understanding of the photochemical behavior of 1,4-dihydropyridines, DFT and TDDFT theoretical calculations are performed. The results provide a good explanation for the formation of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes.
A photocycloaddition reaction of ethyl 1,4-diaryl-1,4-dihydropyridine-3-carboxylate for the construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes is reported for the first time. In order to further investigate this phenomenon and gain a deeper understanding of the photochemical behavior of 1,4-dihydropyridines, DFT and TDDFT theoretical calculations were performed. The results provide a good explanation for the formation of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes. [Display omitted]</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.cclet.2023.108183</doi><tpages>6</tpages></addata></record> |
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| subjects | 1,4-Dihydropyridine 3,9-Diazatetracyclododecanes Photocycloaddition Theoretical investigation |
| title | Construction of 3,9-diazatetraasteranes and 3,9-diazatetracyclododecanes by photocycloaddition reaction of 1,4-dihydropyridines: Experimental and theoretical investigation |
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