Computational study of an oxetane 4H-pyrazole as a Diels–Alder diene

Levandowski, Brian J.; Abularrage, Nile S.; Graham, Brian J.; Raines, Ronald T.

doi:10.1016/j.tetlet.2023.154768

Tetrahedron Letters

2023

DOI: 10.1016/j.tetlet.2023.154768

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Computational study of an oxetane 4H-pyrazole as a Diels–Alder diene

Brian J. Levandowski,

Nile S. Abularrage,

Brian J. Graham

et al.

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2024

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Cited by 1 publication

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Taming the 1,5‐sigmatropic shift across protonated spirocyclic 4H‐pyrazoles

Levandowski,

Graham,

Abularrage

et al. 2024

J of Physical Organic Chem

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The condensation of 1,3‐diketones with hydrazine to access 4H‐pyrazoles is a well‐established synthetic route that travels through a 4H‐pyrazol‐1‐ium intermediate. In the route to a 3,5‐diphenyl‐4H‐pyrazole containing a cyclobutane spirocycle, density functional theory calculations predict, and experiments show that the protonated intermediate undergoes a rapid 1,5‐sigmatropic shift to form a tetrahydrocyclopenta[c]pyrazole. Replacing the 3,5‐diphenyl groups with 2‐furanyl groups decreases the calculated rate of the 1,5‐sigmatropic shift by 6.2 × 105‐fold and enables the isolation of new spirocyclic 4H‐pyrazoles for click chemistry.

show abstract

Taming the 1,5‐sigmatropic shift across protonated spirocyclic 4H‐pyrazoles

Levandowski,

Graham,

Abularrage

et al. 2024

J of Physical Organic Chem

View full text Add to dashboard Cite

show abstract

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Computational study of an oxetane 4H-pyrazole as a Diels–Alder diene

Cited by 1 publication

References 20 publications

Taming the 1,5‐sigmatropic shift across protonated spirocyclic 4H‐pyrazoles

Taming the 1,5‐sigmatropic shift across protonated spirocyclic 4H‐pyrazoles

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