- An atom-economic green approach: Oxidative synthesis of functionalized 1,4-dihydropyridines from N,N-dimethylenaminones and amines
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We report the first oxidative condensation between N,N-dimethylenaminones with amines to form 1,4-dihydropyridines in moderate to good yields, promoted by oxone and trifluoroacetic acid in PEG-400. This reaction features an unusual oxidation of in situ fo
- Yu, Fu-Chao,Zhou, Bei,Xu, Hui,Chang, Kwen-Jen,Shen, Yuehai
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- Mannich Reaction with Enaminones: Convenient Synthesis of Functionalized Tetrahydro-pyrimidines, Dihydro-1,3-oxazines, and Dihydro-1,2,4-triazepines
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A series of tetrahydropyrimidines and bis-(tetrahydropyrimidines) was synthesized by Mannich reaction of sec-emaminones with formaldehyde and the appropriate amine or diamine. Whereas the reaction with formaldehyde gave the dihydro-1,3-oxazine. Tetrahydro
- Afsah, Elsayed M.,El-Desoky, El-Sayed I.,Etman, Hassan A.,Youssef, Ibrahim,Soliman, Ahbarah M.
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- Ambient aqueous-phase synthesis of covalent organic frameworks for degradation of organic pollutants
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The development of a mild, low cost and green synthetic route for covalent organic frameworks (COFs) is highly desirable in order to open the door for practical uses of this new family of crystalline porous solids. Herein, we report a general and facile strategy to prepare a series of microporous or mesoporous COFs by a β-ketoenamine based Michael addition-elimination reaction in aqueous systems at ambient temperature and pressure. This synthesis method not only produces highly crystalline and porous COFs, but also can be carried out with a high reaction rate (only 30 min), high yields (as high as 93%) and large-scale preparation (up to 5.0 g). Furthermore, an Fe(ii)-doped COF shows impressive performance in the oxidative degradation of organic pollutants in aqueous medium. This research thus provides a promising pathway to large-scale green preparation of COFs and their potential application in environmental remediation.
- Liu, Yaozu,Wang, Yujie,Li, Hui,Guan, Xinyu,Zhu, Liangkui,Xue, Ming,Yan, Yushan,Valtchev, Valentin,Qiu, Shilun,Fang, Qianrong
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- Visible Light-Induced Thiocyanation of Enaminone C-H Bond to Access Polyfunctionalized Alkenes and Thiocyano Chromones
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The visible light induced C-H bond thiocyanation on the α-site of tertiary enaminones has been realized under metal-free, photocatalytic conditions in the presence of Rose Bengal, which enables the synthesis of thiocyanated alkene derivatives and chromones using NH4SCN as the thiocyano source under an aerobic atmosphere. In addition, employing Ru(bpy)3Cl2·6H2O as the photocatalyst switches the reaction pathway to provide NH2-functionalized thiocyanated enamines via the difunctionalization process consisting of C-H bond thiocyanation and vinyl C-N bond transamination.
- Gao, Yong,Liu, Yunyun,Wan, Jie-Ping
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- Copper-catalyzed carbene insertion and ester migration for the synthesis of polysubstituted pyrroles
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Copper-catalyzed carbene insertion/ester migration/cyclization of enaminones and α-diazo compounds occurred efficiently to afford 2-ester polysubstituted pyrroles under mild conditions in moderate-to-good yields. Substituent functionality was well tolerated and13C-labelled experiments demonstrated 1,2-ester migration during the reaction.
- Li, Mingrui,Sun, Yiming,Xie, Yuxing,Yu, Yang,Huang, Fei,Huang, He
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p. 11050 - 11053
(2020/10/05)
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- Metal-free, green and efficient oxidative α halogenation of enaminones by halo acid and DMSO
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Metal free oxidative halogenation of N-aryl enaminones has been demonstrated using a DMSO-halo acid combination under mild reaction conditions. This strategy allows a facile halogenation of enaminones through α functionalization leading to a broad range o
- Sorabad, Ganesh Shivayogappa,Maddani, Mahagundappa Rachappa
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p. 6563 - 6568
(2019/05/10)
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- COMPOUNDS AND METHODS FOR HEMATOPOIETIC REGENERATION
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The invention relates to compounds that promote hematopoietic regeneration. The invention further relates to methods of promoting hematopoietic regeneration using the novel compounds of the invention.
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Page/Page column 38; 47
(2019/06/17)
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- Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones
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The first example of the use of an N-heterocyclic carbene (NHC) as an organocatalyst for the activation of isocyanides was demonstrated. On the basis of previous reports on the interaction between NHCs and isocyanides, we developed a catalytic cycle invol
- Kim, Jungwon,Hong, Soon Hyeok
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p. 2401 - 2406
(2017/03/11)
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- Transition-metal-free synthesis of β-trifluoromethylated enamines with trifluoromethanesulfinate
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We have developed a transition-metal free trifluoromethylation protocol between enamines and CF3SO2Na. A wide range of β-trifluoromethyl substituted enamines were delivered in moderate to high yields with only E-configurations.
- Jiang, Huanfeng,Huang, Wei,Yu, Yue,Yi, Songjian,Li, Jiawei,Wu, Wanqing
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supporting information
p. 7473 - 7476
(2017/07/12)
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- Base-Promoted Synthesis of N-Substituted 1,2,3-Triazoles via Enaminone-Azide Cycloaddition Involving Regitz Diazo Transfer
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The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various N-substituted 1,2,3-triazoles by employing t-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azi
- Wan, Jie-Ping,Cao, Shuo,Liu, Yunyun
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supporting information
p. 6034 - 6037
(2016/12/09)
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- Novel tetrahydropyrimidine-adamantane hybrids as anti-inflammatory agents: Synthesis, structure and biological evaluation
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A series of novel (3-((3s,5s,7s)-adamantan-1-yl)-1-alkyl/aralkyl/aryl-1,2,3,4-tetrahydroyrimidin-5-yl)(aryl)methanones (5a-j) has been synthesized by the reaction of 1-aryl-3-(alkyl/aralkyl/aryl)aminoprop-2-en-1-ones 3a-j, 1-adamantanamine 4 and formaldehyde under thermal conditions. The structures of the products (5a-j) have been established with the help of spectral and analytical data. The stereochemistry of the products was established by X-ray crystallographic studies of a representative product (3-((3s,5s,7s)-adamantan-1-yl)-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)(4-chlorophenyl) methanone (5g) of the series. The target adamantane-tetrahydropyrimidine hybrids 5a-j were evaluated for their anti-inflammatory activities as a result of which compounds 5e (R=C6H5CH2, Ar=C6H5), 5i (R=CH3, Ar=4-CH3C6H4), 5j (R=C6H5CH2, Ar=4-CH3C6H4) and 5g (R=CH3, Ar=4-ClC6H4) were found to exhibit excellent and promising anti-inflammatory activities.
- Kalita, Utpalparna,Kaping, Shunan,Nongkynrih, Revinus,Singha, Laishram Indira,Vishwakarma, Jai Narain
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p. 2742 - 2755
(2015/02/19)
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- Acetylide Ion (C22-) as a synthon to link electrophiles and nucleophiles: A simple method for enaminone synthesis
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Friendly competition: A three-component reaction system composed of calcium carbide, an aryl aldehyde, and an amine gave enaminones or propargylamines (see picture) in a predictable manner through competitive pathways. The system enables the cost-efficient synthesis of a variety of enaminones from readily accessible small molecules and demonstrates the versatility of the acetylide ion, which can be used to bridge electrophiles and nucleophiles. Copyright
- Yu, Dingyi,Sum, Yin Ngai,Ean, Amanda Chng Cheng,Chin, Mei Ping,Zhang, Yugen
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p. 5125 - 5128
(2013/06/27)
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- A "byproduct-intermediate-product" recycling strategy for multicomponent synthesis of 1,4-dihydropyridines
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A new multicomponent reaction was devised for the synthesis of 2,6-unsubstituted symmetrical 1,4-dihydropyridines. A "byproduct- intermediate-product" recycling process that regenerated the byproduct to product was involved in the reactions, which was abl
- Wan, Jie-Ping,Zhou, Rihui,Liu, Yunyun,Cai, Mingzhong
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p. 2477 - 2482
(2013/03/14)
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- Enantioselective organocatalytic domino synthesis of tetrahydropyridin-2- ols
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The asymmetric synthesis of tetrahydropyridin-2-ols from enals and enaminones is described. The organocatalytic domino reaction involves a Michael addition-hemiaminalization sequence using the Jorgensen-Hayashi catalyst. Dehydration or oxidation leads to the corresponding 1,4-dihydro-pyridines or 3,4-dihydropyridin-2-ones in a one-pot fashion. The Royal Society of Chemistry 2012.
- Wan, Jie-Ping,Loh, Charles C. J.,Pan, Fangfang,Enders, Dieter
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supporting information
p. 10049 - 10051
(2012/11/07)
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- Efficient palladium-catalyzed Suzuki cross-coupling reaction with β-ketoamine ligands
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A series of β-ketoamine ligands with different steric and electronic substituents on the backbone and with aniline moieties have been synthesized and characterized. In the presence of PdCl2, catalytic studies indicated that they are effective l
- Zhou, Zong-Zhou,Liu, Feng-Shou,Shen, Dong-Sheng,Tan, Cheng,Luo, Ling-Yan
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experimental part
p. 659 - 662
(2011/06/21)
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