A sequential one-pot tandem approach for the synthesis of 4-tosyl-5-aryloxazoles from carboxylic acids
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An efficient method for the synthesis of 4-tosyl-5-aryloxazoles directly from aromatic carboxylic acids has been reported. The method involves the conversion of aromatic carboxylic acids to tosyl carboxylates by treating with tosyl chloride in the presence of potassium carbonate and its subsequent reaction with tosylmethyl isocyanide in the presence of sodium hydride to get 4-tosyl-5-aryloxazoles.
KeywordsOxazole tosylmethylisocyanide tandem cyclization one-pot
MPS thanks UGC-SAP DRS III (Grant No. UGC F-540/10/DRS-III (SAP-I) Dated 14-09-2016). Authors are grateful to Institution of Excellence, University of Mysore, Mysuru for spectral analysis. N. Rajeev thanks UGC, New Delhi for providing RGNF.
- 9.Kuang R, Shue H-J, Blythin D J, Shih N-Y, Gu D, Chen X, Schwerdt J, Lin L, Ting P C, Zhu X, Aslanian R, Piwinski J J, Xiao L, Prelusky D, Wu P, Zhang J, Zhang X, Celly C S, Minnicozzi M, Billah M and Wang P 2007 Discovery of a highly potent series of oxazole-based phosphodiesterase 4 inhibitors Bioorg. Med. Chem. Lett. 17 5150CrossRefGoogle Scholar
- 15.Wu B, Wen J, Zhang J, Li J, Xiang Y-Z and Yu X-Q 2009 One-pot van Leusen synthesis of 4,5-disubstituted oxazoles in ionic liquids Synlett 3 500Google Scholar
- 16.Katritzky A R, Chen Y X, Yannakopoulou K and Lue P 1989 Benzotriazol-1-ylmethyl isocyanide, a new synthon for CH-N=C transfer. Syntheses of \(\upalpha \)-hydroxyaldehydes, 4-ethoxy-2-oxazolines and oxazoles Tetreahedron Lett. 30 6657Google Scholar
- 28.Lingaraju G S, Swaroop T R, Vinayaka A C, Sharath Kumar K S, Sadashiva M P and Rangappa K S 2012 An easy access to 4,5-disubstituted thiazoles via base-induced click reaction of active methylene isocyanides with methyl dithiocarboxylates Synthesis 9 1373Google Scholar
- 29.CCDC 1833176 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures