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Journal of Chemical Sciences

, 130:150 | Cite as

A sequential one-pot tandem approach for the synthesis of 4-tosyl-5-aryloxazoles from carboxylic acids

  • Narasimhamurthy Rajeev
  • Toreshettahally R Swaroop
  • Seegehalli M Anil
  • Kuppalli R Kiran
  • Kanchugarakoppal S Rangappa
  • Maralinganadoddi P Sadashiva
Regular Article
  • 40 Downloads

Abstract

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.

Graphical Abstract:

4, 5 di-substituted oxazoles were synthesized via an efficient method directly from aromatic carboxylic acids. The presented 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 yielding 4-tosyl-5-aryloxazoles.

Keywords

Oxazole tosylmethylisocyanide tandem cyclization one-pot 

Notes

Acknowledgements

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.

Supplementary material

12039_2018_1540_MOESM1_ESM.pdf (2.1 mb)
Supplementary material 1 (pdf 2189 KB)

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Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of Studies in ChemistryUniversity of MysoreManasagangothri, MysuruIndia
  2. 2.Department of Studies in Organic ChemistryUniversity of MysoreManasagangothri, MysuruIndia

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