642410-34-2Relevant academic research and scientific papers
Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2
McAllister, Laura A.,Turner, Kristy L.,Brand, Stephen,Stefaniak, Mark,Procter, David J.
, p. 6497 - 6507 (2007/10/03)
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.
The first Pummerer cyclisations on solid phase. Convenient construction of oxindoles enabled by a sulfur-link to resin
McAllister, Laura A.,Brand, Stephen,De Gentile, Remy,Procter, David J.
, p. 2380 - 2381 (2007/10/03)
α-Sulfanyl N-aryl acetamides, attached to resin via the sulfur atom, undergo efficient Pummerer cyclisation upon activation of the sulfur link, to give oxindoles; heterocyclic products can be cleaved from the resin in a traceless manner using samarium(II) iodide.
