- An unusual approach to spirolactones and related structures
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Spirocyclic structures can be obtained by an ipso-type radical cyclisation onto a furan or a suitably substituted pyrrole followed by oxidation of the stabilised radical adduct. The Royal Society of Chemistry 2006.
- Guindeuil, Soizic,Zard, Samir Z.
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Read Online
- Assemblies of 1,4-Bis(diarylamino)naphthalenes and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water
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Host-guest assemblies of a designed 1,4-bis(diarylamino)naphthalene and V-shaped aromatic amphiphiles consisting of two pentamethylbenzene moieties bridged by an m -phenylene unit bearing two hydrophilic side chains emerged as highly reducing photoredox catalysis systems in water. An efficient demethoxylative hydrogen transfer of Weinreb amides has been developed. The present supramolecular strategy permits facile tuning of visible-light photoredox catalysis in water.
- Abe, Manabu,Akita, Munetaka,Chitose, Youhei,Hyodo, Yuki,Koike, Takashi,Takahashi, Keigo,Yoshizawa, Michito
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supporting information
(2021/10/21)
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- Dealkoxylation ofN-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis
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Lewis acid-assisted palladium-catalysed dealkoxylation ofN-alkoxyamides has been developed. This reaction proceeded smoothly with a range ofN-alkoxyamides in the absence of an external reductant, thereby establishing a convenient and reductant-free protocol. In addition, a gram-scale reaction could be achieved. Preliminary mechanistic investigations indicated that β-hydrogen elimination from a palladium alkoxide intermediate generated an intramolecular hydride source.
- Suzuki, Hirotsugu,Shiomi, Takahiro,Yoneoka, Kenji,Matsuda, Takanori
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supporting information
p. 7545 - 7548
(2020/10/15)
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- Rhodium-Catalyzed Electrooxidative C?H Olefination of Benzamides
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Metal-catalyzed chelation-assisted C?H olefinations have emerged as powerful tools for the construction of functionalized alkenes. Herein, we describe the rhoda-electrocatalyzed C?H activation/alkenylation of arenes. The olefinations of challenging electron-poor benzamides were thus accomplished in a fully dehydrogenative fashion under electrochemical conditions, avoiding stoichiometric chemical oxidants, and with H2 as the only byproduct. This versatile alkenylation reaction also features broad substrate scope and used electricity as a green oxidant.
- Ackermann, Lutz,Struwe, Julia,Zhang, Yan
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supporting information
p. 15076 - 15080
(2020/06/20)
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- Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
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Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.
- Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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p. 11823 - 11838
(2019/10/02)
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- Tandem Transformation of Aldoximes to N-Methylated Amides Using Methanol
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Tandem conversion of aldoximes to N-methylated amides with methanol in presence of a single Ru(II) catalyst is accomplished through the Ru(II)-mediated rearrangement followed by the reductive N-methylation. Employing this protocol, several aldoximes were directly transformed to the N-methylated amides using methanol. Kinetic experiments with H218O advocated that the aldoxime is acted as the nucleophile during the aldoxime to amide rearrangement process. Involvement of nitrile intermediate during this transformation is realized from the kinetic study. (Figure presented.).
- Paul, Bhaskar,Maji, Milan,Panja, Dibyajyoti,Kundu, Sabuj
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supporting information
p. 5357 - 5362
(2019/11/14)
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- A use of the carboxamides aryl carbonyl aminolysis method of preparing amide
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The invention discloses a method for preparing amides via a decarbonylation ammonolysis reaction of aryl ester and formamide. The method comprises the following steps: dissolving a palladium catalyst, aryl ester and formamide in a solvent, and stirring fo
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Paragraph 0030; 0032-0035
(2016/10/10)
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- Reductive N-O cleavage of Weinreb amides by sodium in alumina and silica gels: synthetic and mechanistic studies
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The use of sodium in alumina and silica gels for the reductive cleavage of the N-O bond of N-methoxy-N-methylamides, commonly referred to as Weinreb amides, has been investigated. This method reduces a diverse set of Weinreb amides with different function
- Jackson, James E.,O'Brien, Brittany N.,Kedzior, Sonya K.,Fryz, Gage R.,Jalloh, Fatmata S.,Banisafar, Arash,Caldwell, Michael A.,Braun, Max B.,Dunyak, Bryan M.,Dye, James L.
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p. 6227 - 6230
(2015/10/20)
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- Transition metal-free one-pot synthesis of 2-substituted 3-carboxy-4-quinolone and chromone derivatives
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A novel one-pot synthesis of the 2-substituted 3-carboxy-4-quinolone/ chromone derivatives from readily available 3-oxo-3-arylpropanoates and amides/acyl chlorides is reported, without any transition metal aid. The Royal Society of Chemistry 2013.
- Lin, Jian-Ping,Long, Ya-Qiu
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supporting information
p. 5313 - 5315
(2013/06/27)
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- Re/Mg bimetallic tandem catalysis for [4+2] annulation of benzamides and alkynes via C-H/N-H functionalization
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A rhenium-magnesium cocatalyzed [4+2] annulation of benzamides and alkynes via C-H/N-H functionalization is described. The reaction features a divergent and high level of diastereoselectivities, which are readily switchable by subtle tuning of reaction conditions. Thus, a wide range of both cis- and trans-3,4-dihydroisoquinolinones is expediently synthesized in a highly atom-economical manner. Moreover, mechanistic studies unraveled a tandem mode of action between rhenium and magnesium in the catalytic cycles.
- Tang, Qiuzheng,Xia, Dexin,Jin, Xiqing,Zhang, Qing,Sun, Xiao-Qiang,Wang, Congyang
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supporting information
p. 4628 - 4631
(2013/05/21)
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- Copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagents
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The copper-catalyzed N-methylation of amides and O-methylation of carboxylic acids by using peroxides as the methylating reagent are described. Various amides and carboxylic acids were methylated affording N-substituted amides and esters. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process.
- Xia, Qinqin,Liu, Xiaolong,Zhang, Yuejiao,Chen, Chao,Chen, Wanzhi
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supporting information
p. 3326 - 3329
(2013/07/26)
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- Synthesis of N-alkyl and N-aryl isoquinolones and derivatives via Pd-catalysed C-H activation and cyclization reactions
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Relatively less expensive Pd-catalysed oxidative coupling reactions for the preparation of N-alkyl and N-aryl substituted isoquinolones and their derivatives have been developed. A broad reaction scope has been demonstrated. In addition, studies of the reaction additives and mechanistic insights, as well as KIE studies for a better understanding of the reaction pathway, have been discussed.
- Zhang, Nana,Li, Binyao,Zhong, Hongban,Huang, Jianhui
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p. 9429 - 9439
(2013/01/15)
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- Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation
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The oxidative cycloaddition of benzamides and alkynes has been developed. The reaction utilizes Rh(III) catalysts in the presence of Cu(II) oxidants, and is proposed to proceed by N-H metalation of the amide followed by ortho C-H activation. The resultant rhodacycle undergoes alkyne insertion to form isoquinolones in good yield. The reaction is tolerant of extensive substitution on the amide, alkyne, and arene, including halides, silyl ethers, and unprotected aldehydes as substituents. Unsymmetrical alkynes proceed with excellent regioselectivity, and heteroaryl carboxamides are tolerated leading to intriguing scaffolds for medicinal chemistry. A series of competition experiments shed further light on the mechanism of the transformation and reasons for selectivity.
- Hyster, Todd K.,Rovis, Tomislav
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supporting information; experimental part
p. 10565 - 10569
(2010/09/17)
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- Metal-free reductive cleavage of N-O bonds in weinreb amides by an organic neutral super-electron donor
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The scope of neutral organic super-electron donors as reducing agents has been extended to include the reductive cleavage of N-O bonds in Weinreb amides. This methodology proved to be applicable to a large array of substrates to afford their reduced counterparts in good to excellent yields. The variation in reactivity within the set of tested amides is rationalised. Georg Thieme Verlag Stuttgart.
- Cutulic, Sylvain P. Y.,Murphy, John A.,Farwaha, Hardeep,Zhou, Sheng-Ze,Chrystal, Ewan
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experimental part
p. 2132 - 2136
(2009/04/08)
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- QUINOLONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS
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The present invention relates to novel quinolones of Formula I that inhibit inducible NOS synthase together with methods of synthesizing and using the compounds including methods for inhibiting or modulating nitric oxide synthesis and/or lowering nitric oxide levels in a patient by administering the compounds for the treatment of disease.
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Page/Page column 21
(2008/12/06)
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- Alpha- haloenamine reagents
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The present invention describes immobilized haloenamine reagents, immobilized tertiary amides, methods for their preparation, and methods of use.
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- A radical approach to debenzylation of amides
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The deprotection of N-benzylamides can be achieved under neutral conditions by reaction with N-bromosuccinimide in boiling chlorobenzene or ethyl acetate. Good to excellent yields are obtained using either acyclic or cyclic amides.
- Baker, S. Richard,Parsons, Andrew F.,Wilson, Michelle
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p. 331 - 332
(2007/10/03)
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- Synthesis of some novel imidate derivatives of thiophene and furan: Investigations of their metallation properties and some synthetic applications
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Methyl N-methyl and methyl N-(2,4,6-trimethyl)phenyl-2-carboximidates of thiophene and furan have been synthesized in excellent yields by the reactions of sodium methoxide in methanol with the corresponding N-methyl- and N-(2,4,6-trimethyl)phenyl-2-carboxymidoyl chlorides, which in turn, were obtained from their respective secondary amides by refluxing in neat thionyl chloride. A thorough investigation into the directed lithiation properties of the these heteroaryl-2-imidates with various lithiating agents, solvents, and reaction conditions revealed almost exclusive C5-lithiation. This regioselectivity is in contrast to the C3-lithiation reported for the oxazolino functionality (a cyclic imidate). The synthetic utility of the C5-lithiated intermediate of methyl N-methyl-thiophene-2-carboximidate with various electrophiles is demonstrated. C3-Lithiation has been effected in the case of methyl N-methylthiophene-2-carboximidate when the C5-position is blocked with a removable trimethylsilyl group. Methyl thiophene-2-carboximidate, an N-unsubstituted imidate, was found to eliminate methoxide ion and undergo subsequent C5-lithiation to give 5-lithiothiophene-2-carbonitrile with LDA. n-Butyllithium gave rise predominantly to products resulting from nucleophilic addition to the nitrile group.
- Barcock, Richard A.,Chadwick, Derek J.,Storr, Richard C.,Fuller, Lance S.,Young, John H.
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p. 4149 - 4166
(2007/10/02)
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- AN ALTERNATIVE PROCEDURE FOR THE ALUMINUM-MEDIATED CONVERSION OF ESTERS TO AMIDES
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A convenient method has been developed for directly converting esters to amides using reagents derived from the reaction of trimethylaluminum with ammonium chloride, methylamine hydrochloride or dimethylamine hydrochloride.
- Levin, Jeremy I.,Turos, Edward,Weinreb, Steven M.
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p. 989 - 994
(2007/10/02)
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