Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2.
A sulfur HASC (alpha-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.
McAllister
Laura A
LA
Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK.
Turner
Kristy L
KL
Brand
Stephen
S
Stefaniak
Mark
M
Procter
David J
DJ
D003432:Cross-Linking Reagents / Q000737:chemistry*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D012493:Samarium / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*
D003432:Cross-Linking Reagents; D006571:Heterocyclic Compounds; D007211:Indoles; D007454:Iodides; D000078183:Oxindoles; C022960:2-oxindole; D012493:Samarium; D013455:Sulfur; C409809:samarium diiodide