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

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

doi:10.1016/j.tetlet.2023.154768

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

Tetrahedron Lett. 2023 Oct 25:130:154768. doi: 10.1016/j.tetlet.2023.154768. Epub 2023 Sep 26.

Authors

Brian J Levandowski¹, Nile S Abularrage¹, Brian J Graham¹, Ronald T Raines¹

Affiliation

¹ Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139-4307, USA.

Abstract

We combine the effects of spirocyclization and hyperconjugation to increase the Diels-Alder reactivity of the 4H-pyrazole scaffold. A density functional theory (DFT) investigation predicts that 4H-pyrazoles containing an oxetane functionality at the saturated center are extremely reactive despite having a relatively high-lying lowest unoccupied molecular orbital (LUMO) energy.

Keywords: Click chemistry; cycloaddition; density functional theory (DFT).

Abstract

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