Catalysts-Controlled Roles Exchange between 2,3-Diaryl‑2H‑azirines and Acetone: Chemodivergent Synthesis of Pyrroles and 3‑Oxazolines

Catalysts-Controlled Roles Exchange between 2,3-Diaryl‑2H‑azirines and Acetone: Chemodivergent Synthesis of Pyrroles and 3‑Oxazolines

We report two practical and step-economical methodologies for the chemodivergent synthesis of tri-substituted pyrroles and 3-oxazolines from the domino reactions of 2H-azirines and acetone. For instance, acetone served as a nucleophile to react with 2H-azirines under the basic conditions to furnish...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 89; no. 9; pp. 6064 - 6073
Main Authors: Hu, Haipeng, Liu, Yangu, Wang, Beining, Fan, Shangyi, Deng, Rui, Pu, Xiang, Huang, Yu
Format: Journal Article
Language:English
Published: American Chemical Society 03-05-2024
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Summary:We report two practical and step-economical methodologies for the chemodivergent synthesis of tri-substituted pyrroles and 3-oxazolines from the domino reactions of 2H-azirines and acetone. For instance, acetone served as a nucleophile to react with 2H-azirines under the basic conditions to furnish pyrroles. Upon changing the catalyst to TfOH, acetone served as an electrophile to synthesize 3-oxazolines. Moreover, the products could be synthesized on a gram scale, and the possible catalytic cycles were proposed.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00012