1429481-71-9Relevant academic research and scientific papers
Synthesis of Oxindoles and Benzofuranones via Oxidation of 2-Heterocyclic BMIDAs
Seath, Ciaran P.,Fyfe, James W. B.,Molloy, John J.,Watson, Allan J. B.
, p. 891 - 898 (2017/02/15)
The synthesis of functionalized oxindoles and benzofuranones via oxidation of 2-BMIDA indoles and benzofurans, respectively, is described. Interconversion of boron species (BMIDA→BF3K) was necessary to enable oxidation and overcome boronic acid stability issues associated with a difficult BMIDA hydrolysis. Overall, a robust process was developed that allowed access to a small library of oxindole and benzofuranone products and facilitated the step-efficient synthesis of biologically active compounds containing the oxindole pharmaco-phore.
Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(i)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols
Seath, Ciaran P.,Wilson, Kirsty L.,Campbell, Angus,Mowat, Jenna M.,Watson, Allan J.B.
supporting information, p. 8703 - 8706 (2016/07/15)
A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(i)/Pd(0)/Cu(ii) catalysis. 2-Iodoanilines and phenols undergo a Cu(i)/Pd(0)-catalyzed Sonogashira reaction with ethynyl BMIDA followed by in situ Cu(ii)-catalyzed 5-endo-dig cyclization to generate heterocyclic scaffolds with a BMIDA functional group in the 2-position. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.
Synthesis of Oxindoles through the gold-catalyzed oxidation of N-arylynamides
Yang, Liu-Qing,Wang, Kai-Bing,Li, Chuan-Ying
, p. 2775 - 2779 (2013/06/27)
α-Oxo gold carbenoids generated by the oxidation of N-arylynamides can be trapped intramolecularly at the ortho position of the aryl ring to give functionalized oxindoles under mild reaction conditions. Pyridine N-oxide works as the oxidant, ligand, and base in this transformation. Copyright
