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Journal of Chemical Sciences

, 130:120 | Cite as

Regioselective synthesis of pyrrole and indole-fused isocoumarins catalysed by N\(^\wedge \)O chelate ruthenium(II) complex

  • Keisham S Singh
  • Sneha G Sawant
  • Werner Kaminsky
Regular Article

Abstract

Heterocyclic compounds containing pyrrole and indole-fused isocoumarins were obtained from a one-pot synthesis via annulations of N-heterocyclic carboxylic acids and alkynes with N\(^\wedge \)O chelate ruthenium(II) complex, [RuCl(\(\hbox {PySO}_{3})(p\)-cymene)] (\(\hbox {PySO}_{3}\) = 2-pyridinesulfonate) in the presence of Cu(OAc)\(_{2}\hbox {H}_{2}\)O. The reaction proceeds efficiently in DMF but can also be performed in other solvents such as dichloroethane, \(^{t}\)AmOH, and water. The annulations reaction is regioselective when performed 1-methylpyrrole-2-carboxylic acid with 1-phenyl-1-propyne.

GRAPHICAL ABSTRACT

Abstract Pyrrole and indole-fused isocoumarins are obtained from a one-pot synthesis via annulations of heterocyclic acids and alkynes with N\(^\wedge \)O chelate ruthenium(II) complex, [RuCl(\(\hbox {PySO}_{3})(p\)-cymene)](\(\hbox {PySO}_{3}\) = 2-pyridinesulfonate) in the presence of Cu(OAc)\(_{2}\hbox {H}_{2}\)O. The annulation reaction is regioselectively performed with 1-methylpyrrole-2-carboxylic acid and 1-phenyl-1-propyne in DMF.

Keywords

Annulation reaction isocoumarins alkynes ruthenium(II) catalyst regioselection 

Notes

Acknowledgements

KSS thanks the Department of Science and Technology, India for financial support and the Director, CSIR-NIO for providing necessary facilities.

Supplementary material

12039_2018_1519_MOESM1_ESM.pdf (1.2 mb)
Supplementary material 1 (pdf 1222 KB)

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Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  • Keisham S Singh
    • 1
  • Sneha G Sawant
    • 1
  • Werner Kaminsky
    • 2
  1. 1.Bioorganic Chemistry LaboratoryCSIR-National Institute of OceanographyDona PaulaIndia
  2. 2.Department of ChemistryUniversity of WashingtonSeattleUSA

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