Trifluoroacetic acid catalyzed thiophenylmethylation and thioalkylmethylation of lactams and phenols via domino three-component reaction in water

Ramesh Mudududdla, Rohit Sharma, Santosh K. Guru, Manoj Kushwaha, Ajai P. Gupta, Sonali S. Bharate, Subrayashastry Aravinda, Rajni Kant, Shashi Bhushan, Ram A. Vishwakarma, Sandip B. Bharate

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2 Citations (Scopus)

Abstract

An efficient one-pot trifluoroacetic acid catalyzed thiophenylmethylation and thioalkylmethylation of lactams, isatins and phenols via domino three-component coupling (3CC) with thiols and formaldehyde in water has been described. The developed protocol has wide substrate-scope for a variety of thiols, lactams and isatins. Utility of the protocol for ortho-/para- thiophenylmethylation of phenols indicated that reaction proceeds through in situ formation of a thiophenylmethylium cation intermediate. LC-ESIMS-based mechanistic investigation further confirmed formation of this intermediate. For isatins, the N- versus O-thiophenylmethylation was confirmed by recording the X-ray crystal structure of compound 4e. Thionaphthyl analog 3e exhibited significant antiproliferative activity in MCF-7 cells (IC50 8 μM) via apoptosis-induction.

Original languageEnglish
Pages (from-to)14081-14088
Number of pages8
JournalRSC Advances
Volume4
Issue number27
DOIs
Publication statusPublished - 2014
Externally publishedYes

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