A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles

Angela S. Carlson, Alexandru M. Petre, Joseph J. Topczewski

Research output: Contribution to journalArticlepeer-review

Abstract

This report describes the direct synthesis of dihydro-pyrrolo-pyrazole heterocycles from allylic azides and methyl vinyl sulfone. The product results from a complex cascade reaction that is operationally straightforward, with aromatization being the result of a concomitant elimination step. A variety of azides could participate in this reaction (12 examples) and the isolated yields of the desired product ranged from 51%−72%. Lastly the ethylene sulfone group could be removed by heating the product in pyrrolidine.

Original languageEnglish (US)
Article number152860
JournalTetrahedron Letters
Volume67
DOIs
StatePublished - Mar 16 2021

Bibliographical note

Funding Information:
En-chih Liu, Margaret Clapham, and Dr. Victor Young Jr. are thanked for their assistance with X-ray crystallography. This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award Number R35GM124718. We also acknowledge NIH Shared Instrumentation Grant #S10OD011952. A.S.C. gratefully acknowledges support from the Wayland E. Noland Fellowship and UMN Doctoral Dissertation Fellowship.

Publisher Copyright:
© 2021 Elsevier Ltd

Keywords

  • Azide
  • Cascade reaction
  • Pyrazole
  • Pyrrolidine
  • Vinyl sulfone

PubMed: MeSH publication types

  • Journal Article

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