Sharma, Supriya;
Kumar, Akhilesh;
Erande, Rohan D.
Selective Functionalization of Indole: Synthesis of Bioinspired 2,2′‐thiobisindoles, 3‐substituted Oxindoles, and 1‐(chloromethyl) Indoline‐2‐dione in One‐pot manner
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Media type:
E-Article
Title:
Selective Functionalization of Indole: Synthesis of Bioinspired 2,2′‐thiobisindoles, 3‐substituted Oxindoles, and 1‐(chloromethyl) Indoline‐2‐dione in One‐pot manner
Contributor:
Sharma, Supriya;
Kumar, Akhilesh;
Erande, Rohan D.
Description:
<jats:title>Abstract</jats:title><jats:p>Indolyl thioethers and indolin‐2‐one motifs are extremely common in pharmaceuticals and organic materials, therefore developing a method to create these scaffolds is considered to be a vital endeavour in the chemical sciences. Here we have reported a unified strategy developed by the fine‐tuning of catalyst‐solvent combination [SOCl<jats:sub>2</jats:sub> /AlCl<jats:sub>3</jats:sub> in CHCl<jats:sub>3</jats:sub> and SOCl<jats:sub>2</jats:sub>/DMSO (1 : 1) in CHCl<jats:sub>3</jats:sub> at 25 °C] towards selective functionalization of Indole to synthesize 2,2′‐thiobisindoles and 3‐chloro‐3‐alkyl substituted oxindoles selectively in one‐pot manner with good to satisfactory yield (52‐86 %; 26 Examples). In application, reactions of 3‐subsituted indole and isatin derivatives produced the 1‐(chloromethyl) indoline‐2,3‐diones by just changing the reaction condition (60 °C), which shows the synthetic utility of the developed method.</jats:p>