A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles
[Display omitted] •Rapid Synthesis of Complex Hetrocycles.•Interesting Tautomerization.•Allylic Azide Cascade. 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...
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Veröffentlicht in: | Tetrahedron letters 2021-03, Vol.67, p.152860, Article 152860 |
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Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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•Rapid Synthesis of Complex Hetrocycles.•Interesting Tautomerization.•Allylic Azide Cascade.
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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2021.152860 |