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Far Away from Flatland. Synthesis and Molecular Structure of Dihetera[3.3.n]propellanes and Trihetera[3.3.n]propellanes: Advanced Analogues of Morpholine/Piperazine
An approach to di- and trihetera[3.3.n]propellanes (n = 2–4 ), advanced morpholine and piperazine analogues, is developed. The key step of the reaction sequence included a [3 + 2] cycloaddition reaction of unsaturated vicinal dicarboxylic acid derivatives and in situ generated azomethine ylide res...
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Published in: | Journal of organic chemistry 2019-11, Vol.84 (21), p.13908-13921 |
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creator | Sokolenko, Yevhenii M Yurov, Yevhen Yu Vashchenko, Bohdan V Hryshchuk, Oleksandr V Filimonova, Yuliia Ostapchuk, Eugeniy N Artemenko, Artem Zaremba, Oleg V Grygorenko, Oleksandr O |
description | An approach to di- and trihetera[3.3.n]propellanes (n = 2–4 ), advanced morpholine and piperazine analogues, is developed. The key step of the reaction sequence included a [3 + 2] cycloaddition reaction of unsaturated vicinal dicarboxylic acid derivatives and in situ generated azomethine ylide resulting in the formation of the pyrrolidine ring. One more heteroaliphatic ring (i.e., pyrrolidine or tetrahydrofuran) was annelated by nucleophilic cyclization of the appropriate 1,4-dielectrophilic intermediates. There were 11 examples of the title products obtained in 3–5 steps on a multigram scale with 10–72% overall yields. Additionally, molecular structures of homologous dihetera[3.3.n]propellanes, analogues of morpholine, were obtained from X-ray diffraction studies and analyzed using exit vector plots (EVPs). It was shown that the scaffolds obtained are somewhat larger as compared to the parent morpholine and bicyclic 3-oxa-7-azabicyclo[3.3.0]octane. Moreover, despite very similar chemical structures, they provide a very distinct spatial position of heteroatoms, which is clearly seen from the conformation adopted by a formal eight-membered ring including both N and O atoms (i.e., crown, boat–chair, twist chair–chair, and boat–boat for the oxaza[3.3.2]-, -[3.3.3]-, -[4.3.3]propellanes, and 3-oxa-7-azabicyclo[3.3.0]octane, respectively). |
doi_str_mv | 10.1021/acs.joc.9b02067 |
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Synthesis and Molecular Structure of Dihetera[3.3.n]propellanes and Trihetera[3.3.n]propellanes: Advanced Analogues of Morpholine/Piperazine</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An approach to di- and trihetera[3.3.n]propellanes (n = 2–4 ), advanced morpholine and piperazine analogues, is developed. The key step of the reaction sequence included a [3 + 2] cycloaddition reaction of unsaturated vicinal dicarboxylic acid derivatives and in situ generated azomethine ylide resulting in the formation of the pyrrolidine ring. One more heteroaliphatic ring (i.e., pyrrolidine or tetrahydrofuran) was annelated by nucleophilic cyclization of the appropriate 1,4-dielectrophilic intermediates. There were 11 examples of the title products obtained in 3–5 steps on a multigram scale with 10–72% overall yields. Additionally, molecular structures of homologous dihetera[3.3.n]propellanes, analogues of morpholine, were obtained from X-ray diffraction studies and analyzed using exit vector plots (EVPs). It was shown that the scaffolds obtained are somewhat larger as compared to the parent morpholine and bicyclic 3-oxa-7-azabicyclo[3.3.0]octane. Moreover, despite very similar chemical structures, they provide a very distinct spatial position of heteroatoms, which is clearly seen from the conformation adopted by a formal eight-membered ring including both N and O atoms (i.e., crown, boat–chair, twist chair–chair, and boat–boat for the oxaza[3.3.2]-, -[3.3.3]-, -[4.3.3]propellanes, and 3-oxa-7-azabicyclo[3.3.0]octane, respectively).</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kU1LwzAch4Mobk7P3iRHQdrlpW_xNqZTYUNh8yQS0jR1HW1Tk1aZn8cPaqTT23JJQp7nx5_8ADjHyMeI4LGQ1t9o6bMUERTFB2CIQ4K8iKHgEAwRIsSjJKIDcGLtBrkVhuExGFAcIhajeAi-Z8LAyafYwtzoCs5K0Zaizny43NbtWtnCQneFC10q2ZWOXbamk21nFNQ5vCnWqlVGvFCf-vVrY3SjSuer3lqZve_XcJJ9iFqqDE5qUeq3zjkucaFNs9ZlUavxU9E49csdT8FRLkqrznb7CDzPblfTe2_-ePcwncw9QSltvQjnjMUipETSTOFYRmlKEpJQkidxSJkMAqpIGkRCyoDghKiIyixBaZAyiaSiI3DZ57pB391ALa8KK_uJdWc5IQkL44AR6tBxj0qjrTUq540pKmG2HCP-Ww131XBXDd9V44yLXXiXVir75_-6cMBVD_RmZ9y_2L1xP9_em9o</recordid><startdate>20191101</startdate><enddate>20191101</enddate><creator>Sokolenko, Yevhenii M</creator><creator>Yurov, Yevhen Yu</creator><creator>Vashchenko, Bohdan V</creator><creator>Hryshchuk, Oleksandr V</creator><creator>Filimonova, Yuliia</creator><creator>Ostapchuk, Eugeniy N</creator><creator>Artemenko, Artem</creator><creator>Zaremba, Oleg V</creator><creator>Grygorenko, Oleksandr O</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6036-5859</orcidid></search><sort><creationdate>20191101</creationdate><title>Far Away from Flatland. Synthesis and Molecular Structure of Dihetera[3.3.n]propellanes and Trihetera[3.3.n]propellanes: Advanced Analogues of Morpholine/Piperazine</title><author>Sokolenko, Yevhenii M ; Yurov, Yevhen Yu ; Vashchenko, Bohdan V ; Hryshchuk, Oleksandr V ; Filimonova, Yuliia ; Ostapchuk, Eugeniy N ; Artemenko, Artem ; Zaremba, Oleg V ; Grygorenko, Oleksandr O</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-61f997a532c3de17c6bb282832f87539c443e2b46acc42182e63cd80b4b9c0ce3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sokolenko, Yevhenii M</creatorcontrib><creatorcontrib>Yurov, Yevhen Yu</creatorcontrib><creatorcontrib>Vashchenko, Bohdan V</creatorcontrib><creatorcontrib>Hryshchuk, Oleksandr V</creatorcontrib><creatorcontrib>Filimonova, Yuliia</creatorcontrib><creatorcontrib>Ostapchuk, Eugeniy N</creatorcontrib><creatorcontrib>Artemenko, Artem</creatorcontrib><creatorcontrib>Zaremba, Oleg V</creatorcontrib><creatorcontrib>Grygorenko, Oleksandr O</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sokolenko, Yevhenii M</au><au>Yurov, Yevhen Yu</au><au>Vashchenko, Bohdan V</au><au>Hryshchuk, Oleksandr V</au><au>Filimonova, Yuliia</au><au>Ostapchuk, Eugeniy N</au><au>Artemenko, Artem</au><au>Zaremba, Oleg V</au><au>Grygorenko, Oleksandr O</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Far Away from Flatland. Synthesis and Molecular Structure of Dihetera[3.3.n]propellanes and Trihetera[3.3.n]propellanes: Advanced Analogues of Morpholine/Piperazine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2019-11-01</date><risdate>2019</risdate><volume>84</volume><issue>21</issue><spage>13908</spage><epage>13921</epage><pages>13908-13921</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>An approach to di- and trihetera[3.3.n]propellanes (n = 2–4 ), advanced morpholine and piperazine analogues, is developed. The key step of the reaction sequence included a [3 + 2] cycloaddition reaction of unsaturated vicinal dicarboxylic acid derivatives and in situ generated azomethine ylide resulting in the formation of the pyrrolidine ring. One more heteroaliphatic ring (i.e., pyrrolidine or tetrahydrofuran) was annelated by nucleophilic cyclization of the appropriate 1,4-dielectrophilic intermediates. There were 11 examples of the title products obtained in 3–5 steps on a multigram scale with 10–72% overall yields. Additionally, molecular structures of homologous dihetera[3.3.n]propellanes, analogues of morpholine, were obtained from X-ray diffraction studies and analyzed using exit vector plots (EVPs). It was shown that the scaffolds obtained are somewhat larger as compared to the parent morpholine and bicyclic 3-oxa-7-azabicyclo[3.3.0]octane. Moreover, despite very similar chemical structures, they provide a very distinct spatial position of heteroatoms, which is clearly seen from the conformation adopted by a formal eight-membered ring including both N and O atoms (i.e., crown, boat–chair, twist chair–chair, and boat–boat for the oxaza[3.3.2]-, -[3.3.3]-, -[4.3.3]propellanes, and 3-oxa-7-azabicyclo[3.3.0]octane, respectively).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31509707</pmid><doi>10.1021/acs.joc.9b02067</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-6036-5859</orcidid></addata></record> |
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title | Far Away from Flatland. Synthesis and Molecular Structure of Dihetera[3.3.n]propellanes and Trihetera[3.3.n]propellanes: Advanced Analogues of Morpholine/Piperazine |
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