Cs2CO3-Promoted C-3 Alkylation of 4-[(2,2-Difluoroethyl)amino]-5,5-disubstituted Furan-2(5H)-ones with Heteroarylmethyl Chlorides

Zhao, Yu; Liu, Xinlei; Wang, Weiwei; Geng, Rui; Wang, Mingan

doi:10.1055/s-0037-1609548

Synthesis

2018

DOI: 10.1055/s-0037-1609548

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Cs2CO3-Promoted C-3 Alkylation of 4-[(2,2-Difluoroethyl)amino]-5,5-disubstituted Furan-2(5H)-ones with Heteroarylmethyl Chlorides

Yu Zhao

Xinlei Liu

Weiwei Wang

et al.

Abstract: 4-(2,2-Difluoroethylamino)-3-(heteroarylmethyl)-5,5-disubstituted furan-2(5H)-ones were regioselectively synthesized via C-3 alkylation of 4-(2,2-difluoroethylamino)-5,5-disubstituted furan-2(5H)-ones with heteroarylmethyl chlorides using Cs2CO3 as a base in 62–85% yields. Their structures were characterized by 1H and 13C NMR, HRMS (ESI), and X-ray diffraction. This C-alkylation selectivity was rationalized by bulky hindrance and electron-withdrawing effects.

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Design, Synthesis, and Fungicidal Activity of Novel Plant Elicitors Based on a Diversity-Oriented Synthesis Strategy

et al. 2022

J. Agric. Food Chem.

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The novel plant elicitors, 3-benzyl-5-[1-(2-oxo-4-phenyl-1-oxaspiro[4.5]dec-3-en-3-yl)ethylidene]-2-aminoimidazolin-4-one derivatives, were designed based on the diversity-oriented synthesis strategy and synthesized in four steps via the Knoevenagel condensation reaction as the key step. They were characterized by 1H NMR, 13C NMR, HR-ESI-MS, and X-ray diffraction. The position of the CN bond of Z- and E-configuration compounds was determined by X-ray diffraction. The in vivo fungicidal activity evaluation revealed that most of these compounds exhibited remarkable activities (100%) against Pseudoperonospora cubensis at 400 μg/mL, among which compound 8e still exhibited excellent protective activity with a 50% inhibition rate at 0.1 μg/mL. Because the in vitro effect on tested phytopathogens was poor, the mechanism to induce the immune responses and reinforce the resistance of cucumber against Botrytis cinerea was studied. The results indicated that the compound 8e-mediated defense response against B. cinerea was based on the accumulation of pathogenesis-related proteins and cell wall reinforcement by callose deposition. Quantitative analysis of salicylic acid (SA) and jasmonic acid (JA) and the increased expression of induced resistance-related genes and the defense-associated phenylalanine ammonia lyase revealed that the immune response triggered by compound 8e was highly associated with the SA signaling pathway. Significant upregulation of JA-related genes Cs-AOS2 indicated that the JA signaling pathway was also influenced. It was also shown that the plants treated with compound 8e promoted primary root elongation, which resulted in enhanced plant growth. Most importantly, these compounds have completely new structures compared with the traditional plant elicitors. Further research of 8e-mediated plant disease resistance might have a great influence on the development of plant elicitors.

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Design, Synthesis, and Fungicidal Activity of Novel Plant Elicitors Based on a Diversity-Oriented Synthesis Strategy

et al. 2022

J. Agric. Food Chem.

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Cs2CO3-Promoted C-3 Alkylation of 4-[(2,2-Difluoroethyl)amino]-5,5-disubstituted Furan-2(5H)-ones with Heteroarylmethyl Chlorides

Cited by 1 publication

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Design, Synthesis, and Fungicidal Activity of Novel Plant Elicitors Based on a Diversity-Oriented Synthesis Strategy

Design, Synthesis, and Fungicidal Activity of Novel Plant Elicitors Based on a Diversity-Oriented Synthesis Strategy

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