- Pyridine-Enabled C-N Bond Activation for the Rapid Construction of Amides and 4-Pyridylglyoxamides by Cooperative Palladium/Copper Catalysis
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A pyridine-enabled C-N bond activation of peptidomimetics employing cooperative palladium/copper catalysis in water is developed. Diverse amides and 4-pyridylglyoxamides are simultaneously synthesized through two steps from commercially available materials in a rapid, environmentally friendly, and high atom-economical manner.
- Song, Liangliang,Claessen, Sander,Van Der Eycken, Erik V.
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p. 8045 - 8054
(2020/07/15)
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- Friedel-Crafts Chemistry. Part 53. Divergent and Diversity-Oriented Synthesis of Condensed Indole Scaffolds via Friedel-Crafts Ring Closure Approach
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A series of indole-fused medium-sized N-heterocyclic systems 10a-h were prepared from laboratory-synthesized indole-based esters 9a-h via intramolecular Friedel-Crafts cyclizations induced by both trifluoromethanesulfonic acid and AlCl3/CH
- Abd El-Aal, Hassan A. K.,Khalaf, Ali A.
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p. 276 - 287
(2019/01/30)
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- Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides
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A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide.
- Ghosh, Subhash Chandra,Ngiam, Joyce S. Y.,Seayad, Abdul M.,Tuan, Dang Thanh,Chai, Christina L. L.,Chen, Anqi
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p. 8007 - 8015,9
(2012/12/12)
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- Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides
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A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide.
- Ghosh, Subhash Chandra,Ngiam, Joyce S.Y.,Seayad, Abdul M.,Tuan, Dang Thanh,Chai, Christina L.L.,Chen, Anqi
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p. 8007 - 8015
(2013/01/15)
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- Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4- thiadiazoles
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A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity.
- Kumar, Dalip,Kumar, N. Maruthi,Chang, Kuei-Hua,Gupta, Ritika,Shah, Kavita
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scheme or table
p. 5897 - 5900
(2011/10/18)
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- Synthesis of β- And γ-carbolinones via Pd-catalyzed direct dehydrogenative annulation (DDA) of indole-carboxamides with alkynes using air as the oxidant
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A palladium-catalyzed direct dehydrogenative annulation (DDA) of indolecarboxamides with internal alkynes via C-H and N-H bond cleavage using air as the oxidant was developed. With this method, both β- and γ-carbolinones can be easily prepared under the mild conditions.
- Shi, Zhuangzhi,Cui, Yuxin,Jiao, Ning
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supporting information; experimental part
p. 2908 - 2911
(2010/09/18)
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- A domino amidation route to indolines and indoles: Rapid syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine
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(Chemical Equation Presented) When subjected to palladium-catalyzed amidation conditions, 2-triflyloxy phenethyl carbonates undergo, in addition to the expected aryl cross-coupling, an additional amidation with net displacement of the carbonate. The result is a one-step synthesis of indolines which may be oxidized to indoles. The utility of the procedure is illustrated by the two- or three-step syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.
- Ganton, Michael D.,Kerr, Michael A.
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p. 4777 - 4779
(2007/10/03)
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- Fab I inhibitors
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Compounds of formula (I) and (II) are disclosed wherein, R1, R2, R3, R4, X, A, B, D and Q are as disclosed in the specification, and the compounds are FabI inhibitors useful in the treatment of bacterial infecti
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Page column 20
(2010/02/06)
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- Reactions of Vilsmeier Haack reagent with aromatic and heterocyclic aldoximes
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Reactions of Vilsmeier Haack reagent with various aromatic and heterocyclic aldoximes give amides. Nitriles are shown to be the intermediates in this reaction. Vilsmeier Haack reaction with amides in turn furnishes nitriles.
- Kusurkar, Radhika,Goswami, Shailesh,Vyas, Sandhya
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p. 3148 - 3151
(2007/10/03)
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- Benzimidazoles/Imidazoles Linked to a Fibrinogen Receptor Antagonist Template Having Vitronectin Receptor Antagonist Activity
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Vitronectin receptor antagonists having the formula: STR1 which are useful for the treatment of inflammation, cancer and cardiovascular disorders, such as atherosclerosis and restenosis, and diseases wherein bone resorption is a factor, such as osteoporsis.
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- Preparations and Reactions of 2-Cyanoindole Derivatives
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2-Cyano-1-phenylsulfonylindole (1a) and 2-cyano-1-methylindole (1b) were prepared by chemical and electrolytic methods in modest yields.Nucleophiles such as sodium benzenethiolate, butyllithium and lithium dimethylcuprate attacked the sulfonyl group of 1a, whereas they attacked the cyano group of 1b. 1,3-Dipolar cycloadditions of 1a and 1b with 2,4,6-trimethylbenzonitrile oxide occurred at the cyano groups.Electrophilic reactions of 1b with N-bromosuccinimide, Vilsmeir reagent and acetyl chloride afforded the corresponding 3-bromo-, 3-formyl- and 3-acetylindole derivatives in modest or high yields, albeit less rapidly than the reactions of 1-methylindole.Photochemical addition of dimethyl acetylenedicarboxylate to 1b was followed by cleavage of the cyclobutene intermediate to give dimethyl (2-cyano-1-methylbenzazepine)-3,4-dicarboxylate. Key Words Cyanoindoles; Electrophilic reactions; Nucleophilic reactions; Diels-Alder reactions; 1,3-Dipolar cycloadditions; Photochemistry.
- Lin, Chih-Da,Fang, Jim-Min
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p. 571 - 580
(2007/10/02)
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