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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 9
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Original Articles

Molecular hybridization-guided annulation reactions of isatins with 4-methylpent-3-en-2-one: A direct access to spirooxindole tetrahydropyranones

, , , , , , & show all
Pages 1033-1039 | Received 12 Oct 2017, Published online: 26 Mar 2018
 

ABSTRACT

An efficient molecular hybridization strategy has been utilized for the synthesis of pirooxindole tetrahydropyranones 3 through annulation reactions of isatins 1 with 4-methylpent-3-en-2-one 2. Products consist of a pirooxindole tetrahydropyranone scaffold and propan-2-ether unit were smoothly obtained in moderate yields (up to 56% yield). The one-pot, two-step reaction, avoiding the isolation and purification of intermediates C, has proved to be a practical protocol. This protocol leads to new knowledge in the fields of both molecular complexity and the lead compound discovery.

GRAPHICAL ABSTRACT

Additional information

Funding

We are grateful for the financial support from the National Natural Science Foundations of China (No. 81660576, No. 81560563, and No. 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; Qian Ke He LH Zi [2016]7220, [2015]7666, and Qian Ke He Zi [2015]4010) and Major project of the graduate student education teaching reform (Qian Jiao Yan He JG Zi)[2016]06.

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