Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives | Zendy

Kun-Ming Jiang | Zendy; Urarika Luesakul | Zendy; Shu-Yue Zhao | Zendy; Kun An | Zendy; gnuj Muangsin | Zendy; Nouri Neamati | Zendy; Yi Jin | Zendy; Jun Lin | Zendy

Open Access

Tautomeric-Dependent Lactam Cycloaddition with Nitrile Oxide: Facile Synthesis of 1,2,4-Oxadiazole[4,5-a]indolone Derivatives

Author(s) -

Kun-Ming Jiang,

Urarika Luesakul,

Shu-Yue Zhao,

Kun An,

gnuj Muangsin,

Nouri Neamati,

Yi Jin,

Jun Lin

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b00490

Subject(s) - nitrile , oxadiazole , cycloaddition , tautomer , chemistry , indoline , isatin , regioselectivity , ketone , lactam , combinatorial chemistry , cytotoxicity , stereochemistry , organic chemistry , catalysis , biochemistry , in vitro

A concise, metal-free, and gram-scale strategy to convert indoline-2,3-diones to 1,2,4-oxadiazole[4,5- a ]indolones through an improved [3 + 2] cycloaddition of α-ketone-lactam with nitrile oxides has been developed. The lactim form of the resonance structure of isatin in protic solvents is the key active dipolarophile that shows chemo- and regioselectivity under experimental and theoretical conditions. This strategy conveniently enabled the assembly of several 1,2,4-oxadiazole[4,5- a ]indolines with a broad range of functional groups. Compounds 3a and 4b exhibit cytotoxicity in the NCI/ADR-RES, SKOV3, and OVCAR8 cell lines.

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