| Autor: |
Verdoorn DS; Division of Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium.; Organic Chemistry, Aachen-Maastricht Institute for Biobased Materials (AMIBM), Maastricht University, Urmonderbaan 22, 6167RD Geleen, The Netherlands., Ranjan P; Organic Chemistry, Aachen-Maastricht Institute for Biobased Materials (AMIBM), Maastricht University, Urmonderbaan 22, 6167RD Geleen, The Netherlands., de Reuver T; Organic Chemistry, Aachen-Maastricht Institute for Biobased Materials (AMIBM), Maastricht University, Urmonderbaan 22, 6167RD Geleen, The Netherlands., Janssen E; Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecular and Life Sciences (AIMMS), Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081 HZ Amsterdam, The Netherlands., Vande Velde CML; Intelligence in Processes, Advanced Catalysts and Solvents (iPRACS), Faculty of Applied Engineering, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium., Saya JM; Organic Chemistry, Aachen-Maastricht Institute for Biobased Materials (AMIBM), Maastricht University, Urmonderbaan 22, 6167RD Geleen, The Netherlands., Maes BUW; Division of Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium., Orru RVA; Organic Chemistry, Aachen-Maastricht Institute for Biobased Materials (AMIBM), Maastricht University, Urmonderbaan 22, 6167RD Geleen, The Netherlands. |
| Abstrakt: |
A cobalt(II) mediated three-component synthesis of 5-substituted- N -sulfonyl-1,3,4-oxadiazol-2(3 H )-imines using sulfonyl azides, N -isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids has been developed. This one-pot tandem reaction starts with a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza -Wittig reaction. Both the steric constraints of carboxylic acid and the stoichiometry of the employed cobalt salt determine the selectivity toward the two products, i.e. 5-substituted- N -sulfonyl-1,3,4-oxadiazol-2(3 H )-imine versus 5-substituted-4-tosyl-2,4-dihydro-3 H -1,2,4-triazol-3-one. |
