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

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

doi:10.1016/j.tetlet.2021.152860

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

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

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 language	English (US)
Article number	152860
Journal	Tetrahedron Letters
Volume	67
DOIs	https://doi.org/10.1016/j.tetlet.2021.152860
State	Published - 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

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10.1016/j.tetlet.2021.152860

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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.",

keywords = "Azide, Cascade reaction, Pyrazole, Pyrrolidine, Vinyl sulfone",

author = "Carlson, {Angela S.} and Petre, {Alexandru M.} and Topczewski, {Joseph J.}",

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AU - Topczewski, Joseph J.

N1 - 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

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N2 - 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.

AB - 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.

KW - Azide

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KW - Pyrazole

KW - Pyrrolidine

KW - Vinyl sulfone

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

Abstract

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