1130682-67-5Relevant academic research and scientific papers
Exploiting Sm(ii) and Sm(iii) in SmI2-initiated reaction cascades: Application in a tag removal-cyclisation approach to spirooxindole scaffolds
Coote, Susannah C.,Quenum, Seidjolo,Procter, David J.
supporting information; experimental part, p. 5104 - 5108 (2011/08/07)
A tag removal-cyclisation sequence is described that is initiated by reduction using a Sm(ii) species and completed by a Sm(iii) Lewis acid that is formed in an earlier stage. Therefore, the reaction cascade utilises both oxidation states of a samarium reagent in discrete steps and allows access to privileged, pyrrolidinyl-spirooxindole scaffolds and analogues inspired by the anti-cancer natural product spirotryprostatin A. The Royal Society of Chemistry 2011.
Formation of N-heterocycles by the reaction of thiols with glyoxamides: Exploring a connective Pummerer-type cyclisation
Miller, Marc,Vogel, Johannes C.,Tsang, William,Merrit, Andrew,Procter, David J.
scheme or table, p. 589 - 597 (2009/07/18)
The reaction of thiols with glyoxamides provides a convenient method for the generation of thionium ions and the initiation of Pummerer-type reactions. When the glyoxamides contain tethered aromatic nucleophiles, N-heterocycles are formed by a thionium ion cyclisation. The scope and mechanism of the connective Pummerer-type process has been investigated using a range of thiols, Lewis acids and both mono- and bis-glyoxamides. The utility of the process has been illustrated in a synthesis of the indoloquinoline natural product, neocryptolepine. The Royal Society of Chemistry 2009.
