Synthesis of Nitromethyl-Substituted Oxindole Derivatives via a Desulfonylation Cascade

Ben Niu; Ping Xie; Zhaogang Bian; Wannian Zhao; Min Zhang; Yang Zhou; Lei Feng; Charles U. Pittman Jr; Aihua Zhou

doi:10.1055/s-0034-1378947

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(05): 635-638
DOI: 10.1055/s-0034-1378947

letter

Synthesis of Nitromethyl-Substituted Oxindole Derivatives via a Desulfonylation Cascade

Ben Niu

^aPharmacy School, Jiangsu University, Xuefu Road 301, Zhenjiang, Jiangsu 212013, P. R. of China eMail: ahz@ujs.edn.cn

,

Ping Xie

^bScientific Information Research Institute, Jiangsu University (Library), Xuefu Road 301, Zhenjiang, Jiangsu, 212013, P. R. of China

,

Zhaogang Bian

^aPharmacy School, Jiangsu University, Xuefu Road 301, Zhenjiang, Jiangsu 212013, P. R. of China eMail: ahz@ujs.edn.cn

,

Wannian Zhao

^aPharmacy School, Jiangsu University, Xuefu Road 301, Zhenjiang, Jiangsu 212013, P. R. of China eMail: ahz@ujs.edn.cn

,

Min Zhang

^aPharmacy School, Jiangsu University, Xuefu Road 301, Zhenjiang, Jiangsu 212013, P. R. of China eMail: ahz@ujs.edn.cn

,

Yang Zhou

^aPharmacy School, Jiangsu University, Xuefu Road 301, Zhenjiang, Jiangsu 212013, P. R. of China eMail: ahz@ujs.edn.cn

,

Lei Feng

^aPharmacy School, Jiangsu University, Xuefu Road 301, Zhenjiang, Jiangsu 212013, P. R. of China eMail: ahz@ujs.edn.cn

,

Charles U. Pittman Jr

^cMississippi State University, Mississippi State, MS 39762, USA

,

Aihua Zhou*

^aPharmacy School, Jiangsu University, Xuefu Road 301, Zhenjiang, Jiangsu 212013, P. R. of China eMail: ahz@ujs.edn.cn

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Abstract

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Abstract

A cascade reaction giving nitromethyl-substituted oxindole derivatives was developed. The reaction used NaNO₂ as the nitro source and potassium peroxydisulfate as an oxidant. This reaction proceeded via a radical mechanism involving substitution–desulfonlylation–cyclization steps in one pot and afforded good yields under mild conditions without using toxic metal catalysts. The resultant nitromethyl-substituted oxindole derivatives are convenient and valuable structures for different derivative syntheses.

Key words

oxindole - desulfonylation - radical cyclization - potassium peroxydisulfate - sodium nitrite

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Reference and Notes

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10 General Procedure for the Synthesis of Nitromethyl-Substituted Oxindole Derivatives N-Methyl-N-(phenylsulfonyl)methacrylamide (2.0 mmol, 1.0 equiv) was added to a dried sealed tube, followed by the addition of NaHCO₃ (2 mmol, 1.0 equiv), NaNO₂ (4.0 mmol, 2 equiv), K₂S₂O₈ (2.0 equiv), and anhydrous MeCN (2 mL). The reaction mixture was stirred at 120 °C for 18 h. After the reaction was completed, the reaction mixture was cooled down to r.t. and diluted with EtOAc, then the combined organic layers were dried over Na₂SO₄, filtered, and concentrated in vacuum. The residue was purified by flash chromatography (PE–EtOAc, 25:1) to provide the title compound 3a as a sticky solid in a 88% yield. The same procedure for producing other compounds 3b–j.1-Isopropyl-3-methyl-3-(nitromethyl)indolin-2-one (3a)Sticky solid. IR: 2925, 2854, 2359, 1714, 1611, 1556, 1452, 1357, 1213, 754 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.33–7.04 (arom. H, 4H), 4.96 (d, J=13.2 Hz, 1H), 4.77 (d, J=13.6 Hz, 1H), 4.68 (m, 1H), 1.56 (d, J=7.2 Hz, 6H), 1.40 (s, 3H) ppm. ¹³C NMR (100 Hz, CDCl₃): δ = 21.9, 29.4, 31.9, 44.3, 46.8, 79.1, 110.5, 122.6, 129.0, 129.5, 142.4, 177.0. ESI-MS: m/z calcd for C₁₃H₁₆N₂O₃: 249.1239 [M + H]⁺; found: 249.1249.

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