Work

Expanding the Synthetic Scope of Rawal’s Diene: Access to Pyran and Pyrazole Derivatives

Year: 2026

Type: article

Abstract: The study demonstrates the synthetic versatility of Rawal's diene as a key reagent for the scalable synthesis of MedChem-relevant building blocks. The hetero-Diels-Alder cycloaddition with various ketones based on this reagent provides efficient one-step access to a wide array of substituted dihydropyranones in a scalable manner. These derivatives have shown high synthetic potential for further transformations to tetrahydropyranones and various pyrazoles with an uncommon substitution pattern. All these results demonstrated the effectiveness of Rawal's diene for the synthesis of diverse pyranone-based building blocks and its potential for industrial applications.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c02273

Authors: Oleksii I. Shamrai, Eugeniy N. Ostapchuk, Dmytro O. Leha, Evgenij V. Zarudnitskii, Dmytro M. Volochnyuk, Serhiy V. Ryabukhin

Institutions: Institute of Organic Chemistry, Enamine (Ukraine), Taras Shevchenko National University of Kyiv, National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute”

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Academy of Sciences of Ukraine, Ministry of Education and Science of Ukraine

Awards: G1479117883, G5041566156