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. 2018 Oct 1;3(10):12349-12360.
doi: 10.1021/acsomega.8b01857. eCollection 2018 Oct 31.

Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds

Gopathi Ramu  1   2 , Namballa Hari Krishna  1   3 , Gaurav Pawar  3 , K N Visweswara Sastry  1   3 , Jagadeesh Babu Nanubolu  1 , Bathini Nagendra Babu  1   2   3
Affiliations

Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds

Gopathi Ramu et al. ACS Omega. .

Abstract

A mild and efficient solvent-controlled, metal-free switchable 1,3-dipolar cycloaddition/ring contraction or ring expansion domino reaction of 3-ylideneoxindoles with in situ-generated α-aryldiazomethanes has been developed. This domino reaction provided a series of aryl-substituted 3-spirocyclopropyl-2-oxindoles and pyrazoloquinazolinones with excellent regio- and diastereoselectivity from common substrates under varying solvent conditions.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. 1,3-Dipolar Cycloadditions of 3-Ylidene-oxindoles and α-Diazo Compounds for the Synthesis of 3-Spirocyclopropyl-2-oxindoles
Scheme 2
Scheme 2. Gram-Scale Synthesis of Compounds 4a and 5a
Scheme 3
Scheme 3. Plausible Reaction Mechanism
See this image and copyright information in PMC

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