Synthesis of highly substituted 3-arylideneindolin-2-ones

Ong, Duc Nghia; Dittrich, Sebastian; Swyter, Sören; Jung, Manfred und Bracher, Franz (2017): Synthesis of highly substituted 3-arylideneindolin-2-ones. In: Tetrahedron, Vol. 73, No. 38: pp. 5668-5679

Abstract

3-Arylideneindolin-2-ones are an attractive structural class in drug development, including registered drugs and drug candidates for treatment of cancer, Alzheimer's disease, infections and others. While residues at C-5 and C-7 are easily introduced by electrophilic substitution reactions, position 4 is much less accessible. Here we describe a novel and effective synthesis of highly substituted 3-arylideneindolin-2-ones with flexible modification at C-4. Starting from 1,2-dichloro-3-nitrobenzene a central building block, a trihalogenated indolin-2-one, could be prepared in 6 high yielding steps. Subsequent modification of position 4 and 3 of this building block provided a library of highly substituted 4-substituted 3arylidene-6,7-dichloroindolin-2-ones. This 8 step synthetic sequence utilized preferably precipitation and washing processes as method of purification. (C) 2017 Published by Elsevier Ltd.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Pharmacy
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0040-4020
• Language: English