Oxidative sulfonamidomethylation of imidazopyridines utilizing methanol as the main C1 source

Zhao, Xuemei; Huang, En-Ling; Zhu, Yu-Shen; Li, Jing; Song, Bing; Zhu, Xinju; Hao, Xin‐Qi

doi:10.1039/c9ob00596j

Cited by 28 publications

(6 citation statements)

References 77 publications

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“…The rate of mycotoxin degradation was significantly lower in the methanol solution. It has been suggested that methanol is a free radical scavenger [ 94 ]; therefore, radicals generated by EB in methanol were scavenged by methanol molecules. It was concluded that solutions with radical scavenging ability need a higher EB dose.…”

Section: Electron Beam (Eb) Radiationmentioning

confidence: 99%

Application of Novel Non-Thermal Physical Technologies to Degrade Mycotoxins

Yousefi

Mohammadi

Khajavi

et al. 2021

JoF

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Mycotoxins cause adverse effects on human health. Therefore, it is of the utmost importance to confront them, particularly in agriculture and food systems. Non-thermal plasma, electron beam radiation, and pulsed light are possible novel non-thermal technologies offering promising results in degrading mycotoxins with potential for practical applications. In this paper, the available publications are reviewed—some of them report efficiency of more than 90%, sometimes almost 100%. The mechanisms of action, advantages, efficacy, limitations, and undesirable effects are reviewed and discussed. The first foretastes of plasma and electron beam application in the industry are in the developing stages, while pulsed light has not been employed in large-scale application yet.

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Section: Electron Beam (Eb) Radiationmentioning

confidence: 99%

Application of Novel Non-Thermal Physical Technologies to Degrade Mycotoxins

Yousefi

Mohammadi

Khajavi

et al. 2021

JoF

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“…Off-white solid; 1.11 g, 70% yield; the eluent used was ethyl acetate/petroleum ether (55:45, v/v); mp = 180–182 °C (lit., 191–192 °C); 1 H NMR (400 MHz, CDCl 3 ): δ = 8.13 (d, J = 6.9 Hz, 1H), 7.82–7.79 (m, 2H), 7.70 (d, J = 9.1 Hz, 1H), 7.48–7.44 (m, 2H), 7.41–7. 37 (m, 1H), 7.31–7.24 (m, 3H), 6.87–6.83 (m, 2H), 6.78 (dd, J = 8.7, 1.2 Hz, 2H), 4.72 (s, 2H), 3.88 (br s, 1H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ = 147.6, 145.2, 144.7, 133.9, 129.4, 128.7, 128.3, 128.0, 124.9, 124.1, 118.4, 117.6, 116.4, 113.1, 112.5, 38.2; HRMS (ESI) calcd for C 20 H 18 N 3 + [M + H] + 300.1495, found 300.1498.…”

Section: Experimental Sectionmentioning

confidence: 99%

Phenyliodine(III) Diacetate-Mediated 1,2-ipso-Migration in Mannich Bases of Imidazo[1,2-a]pyridines: Preparation of N-Acetoxymethyl/Alkoxymethyl-N-arylimidazo[1,2-a]pyridine-3-amines

et al. 2020

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Phenyliodine(III) diacetate -mediated 1,2-ipso-migration of an imidazo[1,2-a]pyridine ring via the formation of an aziridine intermediate in Mannich bases derived from imidazo[1,2-a]pyridines, 2-pyridylamines or arylamines, and formaldehyde is reported. The imidazo[1,2-a]pyridines bearing different substituents showed excellent migratory aptitude and resulted in corresponding N-acetoxymethyl-, N-alkoxymethyl-, and N-hydroxymethyl-N-arylimidazo[1,2-a]pyridine-3-amine derivatives in moderate to excellent (42 examples; 35−93%) yields. Radical trapping experiments confirmed the involvement of a non-radical intermediate. The developed protocol is amenable for a scale-up reaction, and synthetic utility of N-acetoxymethyl products was demonstrated by transforming them to corresponding N-(pyridin-2-yl)imidazo[1,2-a]pyridin-3-amines.

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“…Recently, Ackermann and Wang groups independently developed C–H chalcogenation of indolines by copper and rhodium catalysis (Scheme b) . As a continuation of our interest in Cu-catalyzed reactions and novel methods for C–H functionalization, we herein report the first example of Cu-catalyzed regioselective C7 sulfonylation of indolines with readily available and environmentally benign arylsulfuryl chlorides via the directing group strategy.…”

Section: Introductionmentioning

confidence: 98%

Cu-Catalyzed Direct C7 Sulfonylation of Indolines with Arylsulfonyl Chlorides

et al. 2019

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An efficient Cu-catalyzed direct sulfonylation of indolines with easily accessible sulfonyl chlorides has been realized under an air atmosphere via a chelation-assisted strategy. This protocol exhibits several unique characteristics, including broad substrate scope, good functional group tolerance, and operational convenience, which enable a regioselective access to a variety of C-7 functionalized indoline scaffolds in moderate to good yields. The mechanistic study reveals that the sulfonyl radical might be involved in this transformation.

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Oxidative sulfonamidomethylation of imidazopyridines utilizing methanol as the main C1 source

Abstract: An efficient one pot, three component synthesis of C3 sulfonamidomethylated imidazopyridines has been disclosed utilizing methanol and DTBP as the major and minor methylene source, respectively.

Cited by 28 publications

References 77 publications

Application of Novel Non-Thermal Physical Technologies to Degrade Mycotoxins

Application of Novel Non-Thermal Physical Technologies to Degrade Mycotoxins

Phenyliodine(III) Diacetate-Mediated 1,2-ipso-Migration in Mannich Bases of Imidazo[1,2-a]pyridines: Preparation of N-Acetoxymethyl/Alkoxymethyl-N-arylimidazo[1,2-a]pyridine-3-amines

Cu-Catalyzed Direct C7 Sulfonylation of Indolines with Arylsulfonyl Chlorides

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