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Journal of Chemical Sciences

, 131:119 | Cite as

Rhodium-catalyzed synthesis of C4-chalcogenoalkylated oxindoles via Sommelet-Hauser type rearrangement of 3-diazoindolin-2-ones

  • Angula Chandra Shekar Reddy
  • Bhojkumar Nayak
  • Pazhamalai AnbarasanEmail author
Regular Article
  • 15 Downloads
Part of the following topical collections:
  1. Special Issue on 150 years of the Periodic Table

Abstract

Efficient rhodium-catalyzed Sommelet-Hauser type rearrangement of 3-diazoindolin-2-ones with α-thioesters has been accomplished for the synthesis of C4-thioalkylated oxindoles. The developed reaction offers the selective functionalization of C4-position of oxindole via generation of S-ylide and [2, 3]-sigmatropic rearrangement and allows access to diverse C4-thioalkylated oxindoles in good to excellent yield. Furthermore, the method was successfully extended to the synthesis C4-selenoalkylated oxindoles employing the corresponding α-selenoester.

Graphic abstract

Efficient rhodium-catalyzed Sommelet-Hauser type rearrangement of 3-diazoindolin-2-ones with α-thio/α-seleno-esters have been disclosed for the synthesis of C4-thio/selenoalkylated oxindoles.

Keywords

α-Thioesters α-selenoesters 3-diazoindolin-2-ones S-ylide Se-ylide oxindoles Sommelet-Hauser rearrangement 

Notes

Acknowledgements

We thank DST-SERB (EMR/2016/003677) for the financial support and DST-FIST for ESI-MS facility. ACSR thanks the Council of Scientific & Industrial Research (CSIR) for fellowship.

Supplementary material

12039_2019_1711_MOESM1_ESM.pdf (1.8 mb)
Supplementary material 1 (PDF 1875 kb)

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Copyright information

© Indian Academy of Sciences 2019

Authors and Affiliations

  1. 1.Department of ChemistryIndian Institute of Technology MadrasChennaiIndia

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