Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo-trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates
A strain-release-driven, cation-templated nucleophilic 7- and 8-exo-trig-cyclization of tethered Boc-protected amines to cyclopropenes is described. The featured reaction proceeds in diastereo- and regioselective fashion and allows for preparation of the corresponding 2,5-diazabicyclo[5.1.0]octan-6...
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| Veröffentlicht in: | Journal of organic chemistry 2018-11, Vol.83 (22), p.13743-13753 |
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| container_issue | 22 |
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| container_title | Journal of organic chemistry |
| container_volume | 83 |
| creator | Maslivetc, Vladimir A Frolova, Liliya V Rogelj, Snezna Maslivetc, Anna A Rubina, Marina Rubin, Michael |
| description | A strain-release-driven, cation-templated nucleophilic 7- and 8-exo-trig-cyclization of tethered Boc-protected amines to cyclopropenes is described. The featured reaction proceeds in diastereo- and regioselective fashion and allows for preparation of the corresponding 2,5-diazabicyclo[5.1.0]octan-6-ones and 2,6-diazabicyclo[6.1.0]nonan-7-ones as sole products in high yields. Preliminary studies on anticancer activities of these novel cyclopropane-fused medium heterocycles were performed. |
| doi_str_mv | 10.1021/acs.joc.8b02062 |
| format | Article |
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Org. Chem</addtitle><date>2018-11-16</date><risdate>2018</risdate><volume>83</volume><issue>22</issue><spage>13743</spage><epage>13753</epage><pages>13743-13753</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>A strain-release-driven, cation-templated nucleophilic 7- and 8-exo-trig-cyclization of tethered Boc-protected amines to cyclopropenes is described. The featured reaction proceeds in diastereo- and regioselective fashion and allows for preparation of the corresponding 2,5-diazabicyclo[5.1.0]octan-6-ones and 2,6-diazabicyclo[6.1.0]nonan-7-ones as sole products in high yields. 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| ispartof | Journal of organic chemistry, 2018-11, Vol.83 (22), p.13743-13753 |
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| language | eng |
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| source | American Chemical Society Journals |
| subjects | amines antineoplastic activity carbamates chemical reactions chemical structure Lewis bases organic chemistry regioselectivity |
| title | Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo-trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates |
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