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

doi:10.1039/c3ra47874b

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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4 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 language	English
Pages (from-to)	14081-14088
Number of pages	8
Journal	RSC Advances
Volume	4
Issue number	27
DOIs	https://doi.org/10.1039/c3ra47874b
Publication status	Published - 2014
Externally published	Yes

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Mudududdla, R., Sharma, R., Guru, S. K., Kushwaha, M., Gupta, A. P., Bharate, S. S., Aravinda, S., Kant, R., Bhushan, S., Vishwakarma, R. A., & Bharate, S. B. (2014). Trifluoroacetic acid catalyzed thiophenylmethylation and thioalkylmethylation of lactams and phenols via domino three-component reaction in water. RSC Advances, 4(27), 14081-14088. https://doi.org/10.1039/c3ra47874b

@article{3891d2909b724520be4b8df773c11528,

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

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.",

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

year = "2014",

doi = "10.1039/c3ra47874b",

language = "English",

volume = "4",

pages = "14081--14088",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "The Royal Society of Chemistry",

number = "27",

}

Mudududdla, R, Sharma, R, Guru, SK, Kushwaha, M, Gupta, AP, Bharate, SS, Aravinda, S, Kant, R, Bhushan, S, Vishwakarma, RA & Bharate, SB 2014, 'Trifluoroacetic acid catalyzed thiophenylmethylation and thioalkylmethylation of lactams and phenols via domino three-component reaction in water', RSC Advances, vol. 4, no. 27, pp. 14081-14088. https://doi.org/10.1039/c3ra47874b

TY - JOUR

T1 - Trifluoroacetic acid catalyzed thiophenylmethylation and thioalkylmethylation of lactams and phenols via domino three-component reaction in water

AU - Mudududdla, Ramesh

AU - Sharma, Rohit

AU - Guru, Santosh K.

AU - Kushwaha, Manoj

AU - Gupta, Ajai P.

AU - Bharate, Sonali S.

AU - Aravinda, Subrayashastry

AU - Kant, Rajni

AU - Bhushan, Shashi

AU - Vishwakarma, Ram A.

AU - Bharate, Sandip B.

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

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U2 - 10.1039/c3ra47874b

DO - 10.1039/c3ra47874b

M3 - Article

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SN - 2046-2069

VL - 4

SP - 14081

EP - 14088

JO - RSC Advances

JF - RSC Advances

IS - 27

ER -

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

Abstract

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