Issue 100, 2015

Synthesis of functionalized isoxazole–oxindole hybrids via on water, catalyst free vinylogous Henry and 1,6-Michael addition reactions

Abstract

Various 3-substituted-3-hydroxy isoxazole–oxindole hybrids were synthesized via the vinylogous Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin using water as a reaction medium under catalyst free conditions at 50 °C. Systematic studies were carried out to understand the role of the water on the reaction by using D2O, brine, ethylene glycol and PEG-400 as a reaction medium along with organic solvents. Among all of these, water (0.170 mol concentration) was found be more efficient giving desired products in 82–99% yields in 45–120 min. Further the quaternary centre (3° alcohol) generated was used for the creation of a double bond which was again used for a 1,6-Michael reaction to produce highly functionalized isoxazole–oxindole derivatives.

Graphical abstract: Synthesis of functionalized isoxazole–oxindole hybrids via on water, catalyst free vinylogous Henry and 1,6-Michael addition reactions

Supplementary files

Article information

Article type
Paper
Submitted
16 Jul 2015
Accepted
21 Sep 2015
First published
21 Sep 2015

RSC Adv., 2015,5, 81768-81773

Synthesis of functionalized isoxazole–oxindole hybrids via on water, catalyst free vinylogous Henry and 1,6-Michael addition reactions

S. Nagaraju, N. Satyanarayana, B. Paplal, A. K. Vasu, S. Kanvah and D. Kashinath, RSC Adv., 2015, 5, 81768 DOI: 10.1039/C5RA14039K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements