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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 11
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Original Articles

Diversity-oriented regioselective domino Michael/Aldol reaction of 3-ylideneoxindoles: A direct access to indanol-fused 3-oxindoles

, , , , , , & show all
Pages 1346-1353 | Received 04 Oct 2017, Published online: 02 Apr 2018
 

ABSTRACT

A diversity-oriented molecular hybridization strategy has been utilized for the synthesis of 2,3-disubstituted 1-indanol-fused 3-oxindoles through a regioselective domino Michael/Aldol reaction of 3-ylideneoxindoles 1 with malononitrile or cyanacetate ethyle 2. Products bearing consecutive stereocenters consist of an oxindole moiety and an indanol core, were smoothly obtained in high yields (up to 92% yield) with good diastereoselectivity (up to 20:1). This protocol also represents the first construction of indanol-fused 3-oxindole scaffolds, thus leading to new knowledge in the fields of both molecular complexity and diversity-oriented synthesis (DOS) and the lead compound discovery. It is also worth mentioning that the reaction was completely regioselective and the competitive regioisomeric products 4 or 5 were not obtained in any case.

GRAPHICAL ABSTRACT

Additional information

Funding

We are grateful for the financial support from the National Natural Science Foundations of China (Nos. 81560563, 81660576, and 81760625); Excellent creative talents of guizhou province (Qian Jiao He KY Zi [(2015)491] and Qian Ke He Zi [2015]4032, [2017]5609); Project of Guizhou province (Qian Ke He Zi ([2016]5623 and [2015]4010); Innovation Fund for graduate students of Guizhou University (2017027) and Major project of the graduate student education teaching reform (Qian Jiao Yan He JG Zi)[2016]06.

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