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Article Abstract
Herein a catalyst-free solvent-controlled method for the divergent synthesis of spirocyclopropyl and spiropyrazoline oxindoles from 3-ylideneoxindoles and ethyl diazoacetate was developed. With ClCHCHCl as the solvent, spirocyclopropyl oxindoles were obtained in moderate to excellent yields, whereas the use of MeOH as solvent afforded spiropyrazoline oxindoles in moderate to good yields. The readily available substrates, simple operation and various product transformations further highlighted the utility of this method.
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Solvent-Controlled Divergent Cyclization of 3-Ylideneoxindoles with Ethyl 2-Diazoacetate: Access to Spirocyclopropyl and Spiropyrazolines Oxindoles.
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School of Chemistry and Chemical Engineering, Guangzhou University, 230 Wai Huan Xi Road, Guangzhou, 510006, China.
Article Synopsis
- A new method for creating spirocyclopropyl and spiropyrazoline oxindoles was developed, using 3-ylideneoxindoles and ethyl diazoacetate without any catalysts.
- The study found that using ClCHCHCl as the solvent produced spirocyclopropyl oxindoles with moderate to excellent yields, while MeOH led to spiropyrazoline oxindoles with moderate to good yields.
- This method is beneficial due to the easy-to-use materials, straightforward procedure, and potential for further transformations of the products.
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State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering , Qingdao University of Science & Technology, Qingdao 266042 , China.
A new CuI/1,10-phen-catalyzed reaction for the synthesis of 3-ylideneoxindoles from readily available isatins and ethyl isocyanoacetate, in which ethyl isocyanoacetate acts as a latent two-carbon donor like the Wittig reagent, is reported. A tandem procedure including 1,3-dipolar cycloaddition/inverse 1,3-dipolar ring opening/olefination allows the preparation of 3-ylideneoxindoles with broad functional group tolerance.
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