- Rhodium(III)/Amine Synergistically Catalyzed Enantioselective Alkylation of Aldehydes with α,β-Unsaturated 2-Acyl Imidazoles
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A synergistic catalysis combination of chiral-at-metal rhodium complex and amine catalyst was developed for enantioselective alkylation of aldehydes with α,β-unsaturated 2-acyl imidazoles. The corresponding adducts were obtained in good yields with excellent enantioselectivities (up to 99% ee).
- Gong, Jun,Li, Kuan,Qurban, Saira,Kang, Qiang
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- Synthesis of Chromone-Containing Allylmorpholines through a Morita–Baylis–Hillman-Type Reaction
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The first example of an unusual addition of chromone-substituted acrylic acid to enamines is described. The process shows high versatility concerning both enamines and chromones. The reaction is catalyzed by tertiary amines and is highly likely of Morita–
- Chernov, Nikita M.,Shutov, Roman V.,Barygin, Oleg I.,Dron, Mikhail Y.,Starova, Galina L.,Kuz'mich, Nikolay N.,Yakovlev, Igor P.
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- Three-Step One-Pot Process of 3-Methyl-5-Benzofuranol from Amine, Aldehydes, and p-Benzoquinone
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3-Methyl-5-benzofuranol was prepared by a one-pot process from morpholine, propionaldehyde, and p-benzoquinone in 85-87% isolated yields. Avoiding the tedious multistep isolation and purification operations, this practical and efficient process dramatically enhanced the production efficiency as well as reduced the amount of chemical wastes of reaction. The scale-up results showed that the performance was maintained, suggesting potential large-scale applications. Furthermore, the synthesis strategy showed high efficiency for a wide range of aliphatic aldehydes and ketone derivatives.
- Liang, Chaoming,Sun, Maolin,Shen, Xinyuan,Shan, Chao,Wang, Weijuan,Cheng, Ruihua,Ye, Jinxing
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p. 810 - 816
(2021/04/05)
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- Divergent pathways to isophthalates and naphthalate esters from methyl coumalate
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Methyl coumalate readily reacts with enamines at ambient temperature to give lactones, which can be further transformed into isophthalates and tetrahydronaphthoates. Both cyclic and acyclic enamines show good reactivity. Dehydrogenation of tetrahydronaphthoate 4a was achieved on a hundred-gram scale.
- Yu, Huangchao,Kraus, George A.
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supporting information
p. 4008 - 4010
(2018/10/04)
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- Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile
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In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b]furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control β-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H … π interactions with Trp105 and Phe178 residues compared to the control β-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation.
- Bian, Jinlei,Li, Xiang,Wang, Nan,Wu, Xingsen,You, Qidong,Zhang, Xiaojin
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- Triazolines. Part 32. Synthesis of 1-Alkyl-2-aminobenzimidazoles from 5-Amino-1-(2-nitroaryl)-1,2,3-triazolines
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5-Amino-1-(2-nitroaryl)-1,2,3-triazolines 5 are converted into 1-alkyl-2-aminobenzimidazoles 7 in refluxing triethyl phosphite.The reaction occurs via thermal rearrangement of 5 followed by nitrogen elimination which produces N2-(2-nitroaryl)am
- Erba, Emanuela,Mai, Giorgio,Pocar, Donato
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p. 2709 - 2712
(2007/10/02)
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- Enamines: Part IV - Synthesis of Nitro Substituted Alkyl Phenyl Ketones
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Nitro substituted alkyl phenyl ketones (V) have been synthesised by reacting nitro substituted benzoyl chlorides (II) with morpholine enamines (I) of aliphatic aldehydes.The resulting acylated enamines (III) on hydrolysis afford the desired V.However, 2-n
- Kulkarni, Sheshgiri N.,Bhamare, N. K.,Kamath, H. V.
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p. 168 - 170
(2007/10/02)
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- The Chemistry of Aryllead(IV) Tricarboxylates. Reaction with Enamines
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The treatment of 1-morhpholinocyclopentene (1a) with p-methoxyphenyllead triacetate (2a) in chloroform provides a simple high-yielding route to 2-(4-methoxyphenyl)cyclopentanone (3a).This arylation reaction of enamines has been investigated with a variety of substrates and a number of aryllead triacetates.The reaction has been found to be very sensitive to steric effects and is thus a useful synthetic method in a relatively small number of cases.Acetoxylation is a major competing reaction with those enamines of cyclic ketones which give a low to moderate yield of arylated product.
- May, George L.,Pinhey, John T.
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p. 1859 - 1871
(2007/10/02)
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