Solid Phase Approaches to N-Heterocycles Using a Sulfur Linker Cleaved by SmI2
A sulfur HASC (α-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck rea...
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| Veröffentlicht in: | Journal of organic chemistry 2006-08, Vol.71 (17), p.6497-6507 |
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| container_end_page | 6507 |
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| container_issue | 17 |
| container_start_page | 6497 |
| container_title | Journal of organic chemistry |
| container_volume | 71 |
| creator | McAllister, Laura A Turner, Kristy L Brand, Stephen Stefaniak, Mark Procter, David J |
| description | A sulfur HASC (α-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reaction followed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electron transfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with a number of reaction types and its utility for library synthesis. |
| doi_str_mv | 10.1021/jo060940n |
| format | Article |
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Org. Chem</addtitle><date>2006-08-18</date><risdate>2006</risdate><volume>71</volume><issue>17</issue><spage>6497</spage><epage>6507</epage><pages>6497-6507</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A sulfur HASC (α-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reaction followed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electron transfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with a number of reaction types and its utility for library synthesis.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16901135</pmid><doi>10.1021/jo060940n</doi><tpages>11</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2006-08, Vol.71 (17), p.6497-6507 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Chemistry Cross-Linking Reagents - chemistry Cyclization Exact sciences and technology Heterocyclic compounds Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic compounds with only one n hetero atom and condensed derivatives Indoles - chemistry Iodides - chemistry Molecular Structure Organic chemistry Preparations and properties Samarium - chemistry Sulfur - chemistry |
| title | Solid Phase Approaches to N-Heterocycles Using a Sulfur Linker Cleaved by SmI2 |
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