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Molecules 2017, 22(4), 645; doi:10.3390/molecules22040645

Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3′-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction

1
Guizhou Medicine Edicine Edible Plant Resources Research and Development Center, College of Pharmacy, Guizhou University, Guiyang 550025, China
2
Key Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
These two authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Wim Dehaen
Received: 23 March 2017 / Revised: 11 April 2017 / Accepted: 13 April 2017 / Published: 17 April 2017
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

Described herein is the development of a facile and efficient methodology for the synthesis of novel turmerone motif-fused 3,3′-pyrrolidinyl-dispirooxindoles 3–5 via a multicomponent 1,3-dipolar cycloaddition of dienones 2 with azomethine ylides (thermally generated in situfrom isatins and proline or thioproline or sarcosine). Products bearing four or three consecutive stereocenters consist of two oxindole moieties and a pyrrolidinyl core, including vicinal spiroquaternary stereocenters fused in one ring structure were smoothly obtained in high yields (up to 93% yield) with good diastereoselectivity (up to >20:1). Another valuable application of this method was for the design of new hybrid architectures for biological screening through the adequate fusion of these sub-units of turmerone and 3,3′-pyrrolidinyl-dispirooxindole, generating drug-like molecules. View Full-Text
Keywords: turmerone motif-fused 3,3′-pyrrolidinyl-dispirooxindoles; vicinal spiroquaternary stereocenters; 1,3-dipolar cycloaddition reaction; azomethine ylides; diastereoselectivity turmerone motif-fused 3,3′-pyrrolidinyl-dispirooxindoles; vicinal spiroquaternary stereocenters; 1,3-dipolar cycloaddition reaction; azomethine ylides; diastereoselectivity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Lin, B.; Zhou, G.; Gong, Y.; Wei, Q.-D.; Tian, M.-Y.; Liu, X.-L.; Feng, T.-T.; Zhou, Y.; Yuan, W.-C. Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3′-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction. Molecules 2017, 22, 645.

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