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Issue 6, 2015
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“On water” direct catalytic vinylogous Henry (nitroaldol) reactions of isatins for the efficient synthesis of isoxazole substituted 3-hydroxyindolin-2-ones

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Abstract

The first example of an “on water” direct catalytic vinylogous Henry addition of 3,5-dialkyl-4-nitroisoxazoles to isatins is described, giving products in excellent yields and up to excellent diastereoselectivities. A remarkable rate-enhancement by water was observed under mild conditions. This approach provides a highly efficient and environmentally benign access to medicinally important isoxazole substituted 3-hydroxy-2-oxindole derivatives.

Graphical abstract: “On water” direct catalytic vinylogous Henry (nitroaldol) reactions of isatins for the efficient synthesis of isoxazole substituted 3-hydroxyindolin-2-ones

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Article information


Submitted
05 Mar 2015
Accepted
13 Apr 2015
First published
15 Apr 2015

Green Chem., 2015,17, 3266-3270
Article type
Communication

“On water” direct catalytic vinylogous Henry (nitroaldol) reactions of isatins for the efficient synthesis of isoxazole substituted 3-hydroxyindolin-2-ones

Y. Zhang, B. Wei, H. Lin, L. Zhang, J. Liu, H. Luo and X. Fan, Green Chem., 2015, 17, 3266
DOI: 10.1039/C5GC00503E

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