Article
Chemistry, Organic
Xiaosheng Luo, Ping Wang
Summary: In this study, the conversion of 4-aryl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions is reported. The reaction proceeds via the homolysis of acyl-DHP under electron activation and resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This methodology shows wider functionality tolerance and synthetic utility for late-stage modification of complex molecules.
Article
Food Science & Technology
Jiechang Chen, Yuanyuan Zhao, Runlin Wu, Tao Yin, Juan You, Benlun Hu, Caihua Jia, Jianhua Rong, Ru Liu, Binjia Zhang, Siming Zhao
Summary: Frying shrimp in high-oleic sunflower oil leads to increased color difference and higher levels of acidity, carbonyls, and total oxidation in the oil. The major oxidation products formed during frying are alkenals, alkadienals, and conjugated hydroperoxides. However, the proportion of oleic acid in the frying oil increases with longer frying times. These findings contribute to our understanding of the oxidative deterioration of high-oleic oils during frying and have important implications for their application properties.
Article
Food Science & Technology
Gangcheng Wu, Shuyan Han, Xu Li, Emad Karrar, Lirong Xu, Qingzhe Jin, Hui Zhang, Xingguo Wang
Summary: The study found that adding phenolic extract from Camellia oleifera seed cake and tertiary butylhydroquinone can effectively inhibit the oxidation of soybean oil during frying, improving antioxidant stability, with phenolic extract showing better antioxidant effects.
LWT-FOOD SCIENCE AND TECHNOLOGY
(2021)
Article
Multidisciplinary Sciences
Xiaochen Wang, Rongxin Yang, Binbing Zhu, Yuxiu Liu, Hongjian Song, Jianyang Dong, Qingmin Wang
Summary: Here, the authors describe a multicatalytic method for the synthesis of beta, gamma-unsaturated ketones via allylic acylation of alkenes. The method combines N-heterocyclic carbene catalysis, hydrogen atom transfer catalysis, and photoredox catalysis for cross-coupling reactions. The method shows excellent site selectivity and could be used for the synthesis of diverse beta, gamma-unsaturated ketones using carboxylic acids and olefins as substrates.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Yue Dong, Xiangmin Li, Peng Ji, Feng Gao, Xiang Meng, Wei Wang
Summary: A direct formylation method using cost-effective deuterated glyoxylic acid as the formylation agent has been developed. This method allows for the synthesis of structurally diverse C1-deuterated 3-formylindoles with high D-incorporation using visible light and air as the terminal oxidant.
Article
Multidisciplinary Sciences
Rong-Hua Wang, Wei-Wei Xu, Hongli Wu, Yue Li, Jiang-Fei Li, Tao Zhang, Genping Huang, Mengchun Ye
Summary: In this study, we report a new phosphine oxide-ligated Ni-Al bimetallic catalyst that can efficiently activate secondary benzylic C-H bonds via 4-membered nickelacycles, leading to the synthesis of high-yield α,β-unsaturated γ-lactams.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Iliyasu Aliyu Bashir, Sunwoo Lee
Summary: Symmetrical anhydrides can be synthesized from activated amides such as N-benzoylsaccharins and N-Boc-protected benzamides. The reaction of activated amides with H2O in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 25 degrees C can efficiently cleave the C-N bond and yield the corresponding symmetrical anhydrides in high yields. Additionally, N-benzoylsaccharins can react with benzoic acid derivatives to generate unsymmetrical anhydrides in high yields.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiao Zhang, Yang Yu, Wenjie Li, Lei Shi, Hao Li
Summary: A flexible metal-free cascade reaction involving aerobic C(sp(3))-H hydroxylation and decarbonylation with high regioselectivity and functional group tolerance has been established. This indirect hydroxylation approach of N-aryl amides enables the construction of a wide range of valuable secondary alcohols at the a-position of N-aryl amides, providing a supplementary strategy for direct alpha-hydroxylation of simple amides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Muhammad Idham Darussalam Mardjan, Muhamad Fadhly Hariadi, Indah Mutiara Putri, Nilna Amalia Musyarrofah, Muflihah Salimah, Bambang Purwono, Laurent Commeiras
Summary: A small library of 3-hydroxyisoindolin-1-ones has been successfully prepared from 3-alkylidenephtalides under ultrasonic irradiation, showcasing group tolerance, high efficiency, and yields. The reaction can be scaled up to multigram levels and further extended to access other motifs of isoindolin-1-ones in a one-pot fashion.
Article
Chemistry, Organic
Rui-Qi Wang, Qing-Hui Jiang, Hui-Xiang Wang, Xiao-Wei Zhang, Nan Yan
Summary: An efficient electrochemical dehydrogenative cross-coupling of benzylic C-H bonds with 1-thiosugars at room temperature is reported, providing facile access to various glycosylated xanthene derivatives with high yields. This reaction exhibits high atom economy, efficiency, mild reaction conditions, environmental friendliness, and excellent functional group tolerance. Preliminary mechanistic investigations suggest that the reaction proceeds through a free radical process.
Article
Chemistry, Organic
Zhenhua Xu, Hongbiao Chen, Guo-Jun Deng, Huawen Huang
Summary: A copper-based catalytic system has been developed for the formal [3 + 1 + 2] annulations of ketoxime acetates, aldehydes, and cyanamides, providing a new strategy for the synthesis of highly substituted 2-aminopyrimidine compounds. Pyrimidines have now been included in the N-heterocycle family constructed using O-acyl ketoximes as N-C-C synthons.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Jing Ren, Kaiyun Liu, Xiangxiang Kong, Kaizhi Li
Summary: A novel method for the regioselective synthesis of 2-amino-1-naphthols through cascade oxidative annulation of N-acyl-2-aminoacetophenones and alkynes has been successfully developed. This protocol uses no metal catalysts and could be performed with easily available substrates in a single step. The method exhibits broad substrate scope with good functional group compatibility and is amenable for late-stage functionalization of natural compounds and biologically relevant motifs. Mechanistic studies indicated that the additive lithium chloride was effective in the stabilization of persistent C-radical intermediates from N-acyl-2-aminoacetophenone.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Min Liu, Kelu Yan, Jiangwei Wen, Weihua Liu, Mingyu Wang, Lina Wang, Xiu Wang
Summary: A method using rhodium(III) catalysis for the synthesis of substituted 1-hydroxy-2-naphthaldehydes through the reaction of enaminones with vinylene carbonate has been proposed, providing an alternative approach for the synthesis of these compounds with yields ranging from 49-84%. Preliminary mechanistic studies and hydroxyl-directed derivatization reactions of 1-hydroxy-2-naphthaldehydes were also conducted.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Food Science & Technology
Jia Chen, Lingyan Zhang, Altayuly Sagymbek, Qi Li, Yuan Gao, Xiuzhu Yu
Summary: This research used FTIR and H-1 NMR techniques to determine the influence of frying on the oxidation products in polar compounds extracted from different vegetable oils. The study found significant changes in absorption band intensity and the presence of various acyl groups, 1,2-diglycerides, and oxygenated compounds in the polar compounds. The aldehyde and alcohol contents were higher in soybean and rapeseed oils compared to palm oil. Therefore, palm oil was found to be safer in terms of toxic aldehyde content.
JOURNAL OF FOOD PROCESSING AND PRESERVATION
(2022)
Article
Chemistry, Organic
Naya A. A. Stini, Efthymios T. T. Poursaitidis, Nikolaos F. F. Nikitas, Michail Kartsinis, Nikoleta Spiliopoulou, Phoebe Ananida-Dasenaki, Christoforos G. G. Kokotos
Summary: The hydroacylation of dialkyl azodicarboxylates has attracted significant attention recently due to the importance of acyl hydrazides in organic chemistry. In this study, an inexpensive and environmentally friendly photochemical approach using light irradiation (390 nm) and water as the solvent was developed to accelerate the reaction between dialkyl azodicarboxylates and aldehydes. Various aromatic and aliphatic aldehydes were efficiently converted into their corresponding acyl hydrazides in short reaction times (15-210 min) and the reaction mechanism was investigated. The application of this reaction in the synthesis of Vorinostat and Moclobemide was also demonstrated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Food Science & Technology
Barbara Nieva-Echevarria, Encarnacion Goicoechea, Maria D. Guillen
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION
(2020)
Review
Food Science & Technology
Sofia del Cano-Ochoa, Ainhoa Ruiz-Aracama, Maria D. Guillen
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY
(2019)
Article
Food Science & Technology
Andrea Martinez-Yusta, Maria D. Guillen
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY
(2019)
Article
Agriculture, Multidisciplinary
Ana S. Martin-Rubio, Patricia Sopelana, Maria D. Guillen
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
(2019)
Article
Food Science & Technology
A. S. Martin-Rubio, P. Sopelana, Maria D. Guillen
LWT-FOOD SCIENCE AND TECHNOLOGY
(2019)
Article
Food Science & Technology
Barbara Nieva-Echevarria, Encarnacion Goicoechea, Maria D. Guillen
FOOD RESEARCH INTERNATIONAL
(2019)
Article
Biochemistry & Molecular Biology
Ana S. Martin-Rubio, Patricia Sopelana, Fumie Nakashima, Takahiro Shibata, Koji Uchida, Maria D. Guillen
Article
Food Science & Technology
Barbara Nieva-Echevarria, Encarnacion Goicoechea, Maria D. Guillen
FOOD RESEARCH INTERNATIONAL
(2020)
Article
Chemistry, Applied
Jon Alberdi-Cedeno, Mitsy Molina, Berenice Yahuaca-Juarez, Maria L. Ibargoitia, Maria D. Guillen
Article
Biochemistry & Molecular Biology
Jon Alberdi-Cedeno, Maria L. Ibargoitia, Maria D. Guillen
Article
Biochemistry & Molecular Biology
Jon Alberdi-Cedeno, Maria L. Ibargoitia, Maria D. Guillen
Article
Biochemistry & Molecular Biology
Jon Alberdi-Cedeno, Maria L. Ibargoitia, Maria D. Guillen
Article
Biochemistry & Molecular Biology
Jon Alberdi-Cedeno, Maria L. Ibargoitia, Maria D. Guillen
Article
Biochemistry & Molecular Biology
Ana S. Martin-Rubio, Patricia Sopelana, Maria D. Guillen
Article
Food Science & Technology
Ana S. Martin-Rubio, Patricia Sopelana, Maria L. Ibargoitia, Maria D. Guillen
Summary: The in vitro digestion process of highly oxidized soybean oil was studied to understand the transformations of oxidized lipids containing potentially toxic compounds. It was found that polyunsaturated group bioaccessibility during digestion was affected by lipolysis and oxidation occurrence. While some oxidation products like epoxy-compounds and hydroxy-compounds persisted or increased, toxic aldehydes decreased during digestion. Additionally, a high ovalbumin proportion in the digestion process reduced oxidation and the concentration of potentially bioaccessible toxic compounds.