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Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams
An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.
Bai, Ya,Shi, Lingling,Zheng, Lianyou,Ning, Shulin,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
supporting information
p. 2298 - 2302
(2021/04/05)

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water
A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is
Li, Tiejun,Peng, Henian,Tang, Wenjun,Tian, Duanshuai,Xu, Guangqing,Yang, He
p. 4327 - 4337
(2021/05/31)

Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation
Despite the electron-deficient nature of the guanidine carbon centers, nucleophilic reactions at these sites have been underdeveloped because of the resonance stabilization of the guanidine group. We propose a guanidine C-N bond substitution strategy entailing the formation of guanidine cyclic diimide (GCDI) structures, which effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine carbon center of GCDIs undergoes nucleophilic substitution reactions with various amines and alcohols.
An, Taeyang,Lee, Yan
supporting information
p. 9163 - 9167
(2021/11/24)

Reduction of Activated Alkenes by PIII/PV Redox Cycling Catalysis
The carbon–carbon double bond of unsaturated carbonyl compounds was readily reduced by using a phosphetane oxide catalyst in the presence of a simple organosilane as the terminal reductant and water as the hydrogen source. Quantitative hydrogenation was observed when 1.0 mol % of a methyl-substituted phosphetane oxide was employed as the catalyst. The procedure is highly selective towards activated double bonds, tolerating a variety of functional groups that are usually prone to reduction. In total, 25 alkenes and two alkynes were hydrogenated to the corresponding alkanes in excellent yields of up to 99 %. Notably, less active poly(methylhydrosiloxane) could also be utilized as the terminal reductant. Mechanistic investigations revealed the phosphane as the catalyst resting state and a protonation/deprotonation sequence as the crucial step in the catalytic cycle.
Longwitz, Lars,Werner, Thomas
supporting information
p. 2760 - 2763
(2020/02/05)

Photoredox/Cobalt-Catalyzed C(sp3)-H Bond Functionalization toward Phenanthrene Skeletons with Hydrogen Evolution
The first example of photoredox strategy for synthesis of phenanthrene skeletons through C(sp3)-H functionalization under external oxidant-free conditions is achieved. This transformation relies on the keto-enol tautomerism of 1,3 dicarbonyl moiety, i.e., the enol form of 1,3-dicarbonyl derivatives with relatively lower oxidation potential can be activated by the excited acridinium photocatalyst. The electron and proton eliminated from the substrate are immediately captured by a cobaloxime catalyst to exclusively afford a-carbonyl radical for highly substituted 10-phenanthrenols in good to excellent yields.
Guo, Jia-Dong,Yang, Xiu-Long,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
supporting information
p. 9627 - 9632
(2020/12/21)

Cu-catalyzed N-3-Arylation of Hydantoins Using Diaryliodonium Salts
A general Cu-catalyzed, regioselective method for the N-3-arylation of hydantoins is described. The protocol utilizes aryl(trimethoxyphenyl)iodonium tosylate as the arylating agent in the presence of triethylamine and a catalytic amount of a simple Cu-salt. The method is compatible with structurally diverse hydantoins and operates well with neutral aryl groups or aryl groups bearing weakly donating/withdrawing elements. It is also applicable for the rapid diversification of pharmaceutically relevant hydantoins.
Neerbye Berntsen, Linn,Nova, Ainara,Wragg, David S.,Sandtorv, Alexander H.
p. 2687 - 2691
(2020/04/10)

Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides
We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.
Yuan, Yu-Chao,Bruneau, Christian,Dorcet, Vincent,Roisnel, Thierry,Gramage-Doria, Rafael
p. 1898 - 1907
(2019/02/05)

Catalytic Transfer Hydrogenation Using Biomass as Hydrogen Source
We developed an operationally simple method for the direct use of biomass-derived chemical entities in a fundamentally important process, such as hydrogenation. Various carbohydrates, starch, and lignin were used for stereoselective hydrogenation. Employing a transition metal catalyst and a novel catalytic system, the reduction of alkynes, alkenes, and carbonyl groups with high yields was demonstrated. The regioselective hydrogenation to access different stereoisomers was established by simple variations in the reaction conditions. This work is based on an unprecedented catalytic system and represents a straightforward application of biomass as a reducing reagent in chemical reactions.
Antonchick, Andrey P.,Manna, Srimanta
p. 3094 - 3098
(2018/09/14)

Iron(III) Chloride/Phenylsilane-Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly-Substituted γ-Butyrolactones
A iron-catalyzed free radical cascade reaction of allyl alcohols with N-substituted maleimides for accessing poly-substituted γ-butyrolactones has been developed. In this protocol, various allyl alcohols can open N-substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical addition cyclization to form a polysubstituted γ-butyrolactones. In this protocol, spiro γ-butyrolactone compounds can be also synthesized. Meanwhile, the strategy could be applied to further construct a fully substituted tetrahydrofuran. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. (Figure presented.).
Zhang, Hua,Zhan, Xiao-Yu,Chen, Xu-Ling,Tang, Lei,He, Shuai,Shi, Zhi-Chuan,Wang, Yu,Wang, Ji-Yu
p. 4919 - 4925
(2019/11/03)

Simple and efficient synthesis of N-alkyl and N-aryl succinimides in hot water
A new, simple synthesis of succinimides is described. The reactions were carried out under the ultimate green conditions excluding both catalyst and organic solvent by applying simple stirring at 100 °C. A wide variety of N-susbstituted succinimides have been prepared in high yields by using succinic acid and primary amines in hot water. Yield of N-alkyl substituted succinimides were found to be higher than those of N-aryl substituted succinimides.
Bozdo?an, Burcu,Er?at?r, Mehmet,Demirkol, Onur,Akba?lar, Dilek,Giray, E. Sultan
p. 217 - 223
(2017/01/22)

Metal-Free Synthesis of N-Aryl Amides using Organocatalytic Ring-Opening Aminolysis of Lactones
Catalytic ring-opening of bio-sourced non-strained lactones with aromatic amines can offer a straightforward, 100 % atom-economical, and sustainable pathway towards relevant N-aryl amide scaffolds. Herein, the first general, metal-free, and highly efficient N-aryl amide formation is reported from poorly reactive aromatic amines and non-strained lactones under mild operating conditions using an organic bicyclic guanidine catalyst. This protocol has high application potential as exemplified by the formal syntheses of drug-relevant molecules.
Guo, Wusheng,Gómez, José Enrique,Martínez-Rodríguez, Luis,Bandeira, Nuno A. G.,Bo, Carles,Kleij, Arjan W.
p. 1969 - 1975
(2017/05/16)

Efficient copper-catalyzed N-arylation of NH-containing heterocycles and sulfonamides with arenediazonium tetrafluoroborates
A practical copper-catalyzed N-arylation of NH-containing heterocycles with arenediazonium tetrafluoroborates has been developed using CuCl as catalyst and K2CO3 as additive under ligand-free conditions. This reaction system has wide substrate scope including imides, 1H-pyrazole, 1H-tetrazoles, 1,2-benzisothiazol-3(2H)-one, and related sulfonamides and gives moderate to excellent yields (up to 95%) of the desired products. This strategy is very general, simple, environmentally friendly, and tolerant of oxygen.
Ouyang, Yu-Qing,Yang, Zhen-Hua,Chen, Zhong-Hui,Zhao, Sheng-Yin
supporting information
p. 771 - 778
(2017/04/06)

An Efficient One-Pot Synthesis of Bis Butenolides
3,3′,4,4′-Tetramethyl-5,5′-dioxo-2,2′-bifuran-2,2′(5H,5′H) diyl diacetate was obtained from the reaction between 2,3-dimethyl maleic anhydride and acetic anhydride in the presence of zinc in toluene. This easy synthetic route gave bis butenolide in excellent yield.
Bayat, Mohammad,Fox, Joseph M.
p. 1661 - 1664
(2016/09/23)

Direct Synthesis of Cyclic Imides from Carboxylic Anhydrides and Amines by Nb2O5 as a Water-Tolerant Lewis Acid Catalyst
In the 20 types of heterogeneous and homogenous catalysts screened, Nb2O5 showed the highest activity for the synthesis of N-phenylsuccinimide by dehydrative condensation of succinic anhydride and aniline. Nb2O5 was used in the direct imidation of a wide range of carboxylic anhydrides with NH3 or amines with various functional groups and could be reused. Kinetic studies showed that the Lewis acid Nb2O5 catalyst was more water tolerant than both the Lewis acidic oxide TiO2 and the homogeneous Lewis acid ZrCl4, which resulted in higher yields of imides through the use of Nb2O5. Int-imidation tactics: A general method for the direct synthesis of cyclic imides from cyclic anhydrides with amines (or ammonia) under solvent-free conditions is reported. Kinetic studies indicate that the Lewis acid sites of Nb2O5 are highly water tolerant, which results in high catalytic activity for imidation even in the presence of water formed during the reaction. The catalyst can be recovered and reused four times without a marked decrease in yield.
Ali, Md. A.,Moromi, Sondomoyee K.,Touchy, Abeda S.,Shimizu, Ken-Ichi
p. 891 - 894
(2016/03/15)

REDUCTION METHOD USING WATER AS PROTON SOURCE BY MEANS OF N-HETEROCYCLIC CARBENE
PROBLEM TO BE SOLVED: To provide a reduction method using water as a proton source by means of N-heterocyclic carbene, in which the N-heterocyclic carbene is used actively as a reaction accelerator to realize a hydrogenation reaction by using water as the proton source. SOLUTION: A solution, which is obtained by mixing: a reaction substrate shown at an upper stage of the following formulae; a precursor of the triazole-based N-heterocyclic carbene (NHC) shown at a lower stage; water; and 1,2-dimethoxyethane being a solvent, is reacted at 100°C or higher temperature for 2 hours or more while making the solution to pass through a microwave reaction unit and the reacted solution is subjected to reduced-pressure distillation to obtain a hydrogenated product. The formulae: (EWG1-EWG4 are each an ester group, a cyano group, a ketone group, an amido group or an imido group;R1-R5 are each a 1-20C aliphatic group, a 3-12C alicyclic group or 6-30C aromatic group) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0014; 0015; 0022

(2016/10/10)

Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: Application to the synthesis of vernakalant
Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.
Garad, Dnyaneshwar N.,Tanpure, Subhash D.,Mhaske, Santosh B.
supporting information
p. 1008 - 1016
(2015/08/18)

Transfer hydrogenation promoted by N-heterocyclic carbene and water
N-Heterocyclic carbenes (NHCs) promote the transfer hydrogenation of various activated C=C, C=N, and N=N bonds with water as the proton source. The NHCs act as reducing reagents to be converted into their oxides. A detailed reaction mechanism is proposed on the basis of deuterium-labeling experiments.
Kato, Terumasa,Matsuoka, Shin-Ichi,Suzuki, Masato
supporting information
p. 13906 - 13909
(2015/09/07)

Synthesis of novel N-aryl-3-dialkylamino-4-substituted maleimides
The syntheses of several novel 3-dialkylamino-N-aryl-maleimides 3a-i and 6 are described via a conjugate elimination addition-elimination pathway. Syntheses of their various 4-substituted derivatives 4a-i, 5a-c and 7-12 are also described. Introduction of a secondary amino group at C-3 position in N-arylmaleimides leads to the formation of enaminones 3a-i and 6, which undergo facile electrophilic substitutions at C-4 position in good to excellent yields to provide the highly functionalized maleimides 4a-i, 5a-c and 7-12.
Patil, Nilesh S.,Deshmukh, Ganesh B.,Mahale, Keshao A.,Gosavi, Kirankumar S.,Patil, Sambhaji V.
p. 272 - 278
(2015/03/04)

A convenient one-pot synthesis of polysubstituted pyrroles from N-protected succinimides
The dienamine products formed by the reaction between polysubstituted succinimides and the Petasis reagent were subjected to isomerization under mild acidic conditions to give polysubstituted pyrroles in excellent yields (85-95%). The scope and limitations of this methodology are explored.
Kobeissi, Marwan,Yazbeck, Ogaritte,Chreim, Yamama
supporting information
p. 2523 - 2526
(2014/05/06)

Versatile and sustainable synthesis of cyclic imides from dicarboxylic acids and amines by Nb2O5 as a base-tolerant heterogeneous lewis acid catalyst
Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom-efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb2O5 as a reusable and base-tolerant heterogeneous Lewis acid catalyst. The method is effective for the direct synthesis of pharmaceutically or industrially important cyclic imides, such as phensuximide, N-hydroxyphthalimide (NHPI), and unsubstituted cyclic imides from dicarboxylic acid or anhydrides with amines, hydroxylamine, or ammonia.
Ali, Md. Ayub,Siddiki, S. M. A. Hakim,Kon, Kenichi,Hasegawa, Junya,Shimizu, Kenichi
supporting information
p. 14256 - 14260
(2015/01/09)

An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters
Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.
Kumar, Padam Praveen,Reddy, Y. Dathu,Kumari, Y. Bharathi,Devi, B. Rama,Dubey
p. 392 - 398
(2014/05/06)

Selective formation of α,ω-ester amides from the aminocarbonylation of castor oil derived methyl 10-undecenoate and other unsaturated substrates
The reaction of long chain alkenes with CO and aniline in the presence of palladium complexes of 1,2-bis-(ditertbutylphosphinomethyl)benzene produces amides with high linear selectivity, with much higher rates and catalyst stability when 2-naphthol and sodium or potassium iodide are added. Unsaturated esters including methyl 10-undecenoate from castor oil give α,ω- ester amides, whilst reactions in THF give N-phenylpyrrolidine.
Jimenez-Rodriguez, Cristina,Nunez-Magro, Angel A.,Seidensticker, Thomas,Eastham, Graham R.,Furst, Marc R. L.,Cole-Hamilton, David J.
p. 2332 - 2339
(2014/07/22)

Hydrogenations without hydrogen: Titania photocatalyzed reductions of maleimides and aldehydes
A mild procedure for the reduction of electron-deficient alkenes and carbonyl compounds is described. UVA irradiations of substituted maleimides with dispersions of titania (Aeroxide P25) in methanol/acetonitrile (1:9) solvent under dry anoxic conditions led to hydrogenation and production of the corresponding succinimides. Aromatic and heteroaromatic aldehydes were reduced to primary alcohols in similar titania photocatalyzed reactions. A mechanism is proposed which involves two proton-coupled electron transfers to the substrates at the titania surface.
Manley, David W.,Buzzetti, Luca,MacKessack-Leitch, Andrew,Walton, John C.
p. 15324 - 15338
(2015/01/16)

Heterologous expression and characterization of the ene-reductases from Deinococcus radiodurans and Ralstonia metallidurans
The Old Yellow Enzyme (OYE) homologues or ene-reductases (ER) from Deinococcus radiodurans (DrER) and Ralstonia metallidurans (RmER) were cloned and characterized. Sequence and phylogenetic analysis revealed both these enzymes to belong to the YqjM-like or "thermophilic-like" group of OYEs, both sharing more than 60% sequence similarity to the ER from Thermus scotoductus. This group of OYEs is characterized by a conserved cysteine residue modulating the redox potential of the flavin cofactor as well as a conserved tyrosine residue located at the N-terminus region involved in binding certain ligands. The genes were recombinantly expressed in Escherichia coli as functional soluble proteins. Both ERs have monomer molecular weights of approximately 40 kDa, with DrER a homodimer in solution and RmER a monomer. DrER and RmER are optimally active at pH 7-7.5 at 30 C and 35 C respectively. Although the enzymes showed comparable affinities towards the ubiquitous ER substrate 2-cyclohexenone, the specific activity and catalytic efficiency of DrER were more than twice those observed for RmER. Similar to other members of this subclass of ERs, no conversion was detected with cyclic Cβ substituted enones, and only DrER was able to convert citral. Both DrER and RmER were highly active at reducing N-phenyl substituted maleimides. The selectivity of the ERs was assessed using both the isomers of carvone, which were converted with high diastereomeric excesses. Ketoisophorone and 2-methylcyclopentenone were converted to their (R)- and (S)-enantiomeric products respectively. Finally, a light-driven cofactor regeneration system was used to drive enzymatic reduction in the absence of NAD(P)H.
Litthauer,Gargiulo,Van Heerden,Hollmann,Opperman
p. 89 - 95
(2014/01/06)

Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis
The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.
Kim, Hyejin,Kim, Taehoon,Lee, Dong Gil,Roh, Sang Weon,Lee, Chulbom
supporting information
p. 9273 - 9276
(2014/08/05)

A mild, ferrocene-catalyzed C-H imidation of (hetero)arenes
A simple method for direct C-H imidation is reported using a new perester-based self-immolating reagent and a base-metal catalyst. The succinimide products obtained can be easily deprotected in situ (if desired) to reveal the corresponding anilines directly. The scope of the reaction is broad, the conditions are extremely mild, and the reaction is tolerant of oxidizable and acid-labile functionality, multiple heteroatoms, and aryl iodides. Mechanistic studies indicate that ferrocene (Cp2Fe) plays the role of an electron shuttle in the decomposition of the perester reagent, delivering a succinimidyl radical ready to add to an aromatic system.
Foo, Klement,Sella, Eran,Thomé, Isabelle,Eastgate, Martin D.,Baran, Phil S.
supporting information
p. 5279 - 5282
(2014/05/06)

Titania-promoted carboxylic acid alkylations of alkenes and cascade addition-cyclizations
Photochemical reactions employing TiO2 and carboxylic acids under dry anaerobic conditions led to several types of C-C bond-forming processes with electron-deficient alkenes. The efficiency of alkylation varied appreciably with substituents in the carboxylic acids. The reactions of aryloxyacetic acids with maleimides resulted in a cascade process in which a pyrrolochromene derivative accompanied the alkylated succinimide. The selectivity for one or other of these products could be tuned to some extent by employing the photoredox catalyst under different conditions. Aryloxyacetic acids adapted for intramolecular ring closures by inclusion of 2-alkenyl, 2-aryl, or 2-oximinyl functionality reacted rather poorly. Profiles of reactant consumption and product formation for these systems were obtained by an in situ NMR monitoring technique. An array of different catalyst forms were tested for efficiency and ease of use. The proposed mechanism, involving hole capture at the TiO2 surface by the carboxylates followed by CO2 loss, was supported by EPR spectroscopic evidence of the intermediates. Deuterium labeling indicated that the titania likely donates protons from surface hydroxyl groups as well as supplying electrons and holes, thus acting as both a catalyst and a reaction partner.
Manley, David W.,McBurney, Roy T.,Miller, Phillip,Walton, John C.,Mills, Andrew,O'Rourke, Christopher
supporting information
p. 1386 - 1398
(2014/03/21)

Open-air N-arylation of N-H heterocycles with arylboronic acids catalyzed by copper(II) Schiff base complexes
Two copper Schiff base complexes, in both homogeneous and heterogeneous forms, were prepared and characterized by using elemental analysis, FTIR, UV-Vis spectroscopy and scanning electron microscopy. The catalytic performances of these complexes were studied in the N-arylation of N-H heterocycles with arylboronic acids in methanol without any added base at 40 °C under open air. The effects of various parameters such as solvent and temperature on the reaction system were studied. The reaction is applicable to a wide variety of N-H heterocycles and arylboronic acids. The heterogeneous catalyst was recovered by simple filtration, and reusability experiments showed that this catalyst can be used five times without much loss in the catalytic activity.
Islam,Dey, Ram Chandra,Roy, Anupam Singha,Paul, Sumantra,Mondal, Sanchita
p. 961 - 969
(2015/01/09)

A facile and green synthesis of N-substituted imides
Anhydrides 1, 6 and 10 have been reacted, independently, with aromatic primary amines 2 in solid phase by simple physical grinding of reactants with p-toluenesulphonicacid as a catalyst to yield corresponding open chain derivatives, monoacid monoamides3,7 and 11 respectively. The latter have each been transformed into the corresponding cyclic derivatives, i.e. imides 5, 9 and 13 respectively in solid phase by simple physical grinding of each with K 2CO3, alkylating agent and tetrabutylammoniumbromide as a catalyst with short reaction times. These cyclic imides can also be obtained by physical grinding of each of 3, 7 and 11 with dicyclohexylcarbodimide as a dehydrating agent in solid phase.
Kumar, Padam Praveen,Rama Devi,Dubey
p. 1166 - 1171
(2013/09/24)

Solvent-mediated one-pot synthesis of cyclic N-Substituted imides
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Patil, Sambhaji V.,Mahale, Keshao A.,Gosavi, Kirankumar S.,Deshmukh, Ganesh B.,Patil, Nilesh S.
p. 314 - 320
(2013/07/26)

Mimicking nature: Synthetic nicotinamide cofactors for C=C bioreduction using enoate reductases
A series of synthetic nicotinamide cofactors were synthesized to replace natural nicotinamide cofactors and promote enoate reductase (ER) catalyzed reactions without compromising the activity or stereoselectivity of the bioreduction process. Conversions and enantioselectivities of >99% were obtained for C=C bioreductions, and the process was successfully upscaled. Furthermore, high chemoselectivity was observed when employing these nicotinamide cofactor mimics (mNADs) with crude extracts in ER-catalyzed reactions.
Paul, Caroline E.,Gargiulo, Serena,Opperman, Diederik J.,Lavandera, Iván,Gotor-Fernández, Vicente,Gotor, Vicente,Taglieber, Andreas,Arends, Isabel W. C. E.,Hollmann, Frank
supporting information
p. 180 - 183
(2013/04/24)

Studies on reactions of anhydrides with Schiff bases
Reaction of phthalic anhydride 1 with benzylidineanilines 2, in equimolar ratio in hot acetic acid, yields N-arylphthalimides 3. Compound 1 reacts with the arylimine part of the Schiff base eliminating benzaldehyde part 4 as the bye-product. This reaction of 1 with 2 is also found to occur with other anhydrides like succinic anhydride 5, maleic anhydride 7 and acetic anhydride 9 resulting in the formation of the corresponding N-arylimides, namely, succinicimide 6, maleicimide 8 and aceticimide 10 respectively. In all the above reactions, the by-product, i.e. benzaldehyde or p-chlorobenzaldehyde can be isolated and characterized as its 2,4-dinitrophenylhydrazone derivative. Probable mechanism for the formation of imides from the corresponding anhydrides and Schiff bases has been suggested.
Kumar, Padam Praveen,Mohiuddin,Rama Devi,Dubey
p. 686 - 690
(2013/07/11)

Possible antineoplastic agents, part XVII: Synthesis, antitumor and antiangiogenic study of few bioisosteres of thalidomide metabolites
Two series of bioisostere of thalidomide metabolites and their cyclized variants were designed, synthesized and characterized. In vivo antitumor activity was studied on EAC in swiss albino mice. Cytotoxicity study was carried out on HUVEC and Vero cell lines by MTT assay method. Antiangiogenic activity on Ehrlich ascites tumor (EAT) was investigated studying inhibition of formation of micro vessels by identification of CD31 antigen through immunohistochemistry. One molecule has exhibited both antitumor and antiangiogenic activity but there is no significant toxic effect on normal cell.
Sen,Sarker,Ghosh,Mishra,Saha,Goswami,Gupta,De
experimental part
p. 1872 - 1878
(2012/09/22)

Aromatic-amide-derived olefins as a springboard: Isomerization-initiated palladium-catalyzed hydrogenation of olefins and reductive decarbonylation of acyl chlorides with hydrosilane
A highly efficient catalytic protocol for the isomerization of substituted amide-derived olefins is presented that successfully uses a hydride palladium catalyst system generated from [PdCl2(PPh3)2] and HSi(OEt)3. The Z to E isomerization was carried out smoothly and resulted in geometrically pure substituted olefins. Apart from the cis-trans isomerization of double bonds, the selective reduction of terminal olefins and activated alkenes was performed with excellent functional group tolerance in the presence of an amide-derived olefin ligand, and the products were obtained in high isolated yields (up to >99 %). Furthermore, the palladium/hydrosilane system was able to promote the reductive decarbonylation of benzoyl chloride when a (Z)-olefin with an aromatic amide moiety was used as a ligand. Copyright
Bai, Xing-Feng,Xu, Li-Wen,Zheng, Long-Sheng,Jiang, Jian-Xiong,Lai, Guo-Qiao,Shang, Jun-Yan
supporting information; experimental part
p. 8174 - 8179
(2012/08/27)

Unconventional titania photocatalysis: Direct deployment of carboxylic acids in alkylations and annulations
Under dry, anaerobic conditions, TiO2 photocatalysis of carboxylic acid precursors resulted in carbon-carbon bond-forming processes. High yields of dimers were obtained from TiO2 treatment of carboxylic acids alone. On inclusion of electron-deficient alkenes, efficient alkylations were achieved with methoxymethyl and phenoxymethyl radicals. In reactions with maleic anhydride or maleimides, phenoxyacetic acid produced chromenedione derivatives in addition to adducts. These photocatalytic reactions are simple and cheap to perform, and the TiO2 is easily removed by filtration. The anaerobic photocatalysis strategy offers a range of synthetic possibilities.
Manley, David W.,McBurney, Roy T.,Miller, Phillip,Howe, Russell F.,Rhydderch, Shona,Walton, John C.
supporting information; experimental part
p. 13580 - 13583
(2012/10/08)

Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds
The synthesis, in vitro evaluation and SAR studies of 67 maleimides and derivatives acting as antifungal agents are reported. A detailed SAR study supported by theoretical calculations led us to determine that: an intact maleimido ring appears to be necessary for a strong antifungal activity, dissimilarly affected by the substituents in positions 2 and 3. The best activities were shown by 2,3-nonsubstituted followed by 2,3 dichloro- and 2-methyl-substituted maleimides. They all were fungicide rather than fungistatic enhancing the importance of their antifungal activity. 2,3-Dimethyl and 2,3-diphenyl-maleimides possessed marginal or null activity. The presence of a flexible connecting chain in N-phenylalkyl maleimides appears not to be essential for antifungal activity, although its length shows a correlation with the antifungal behavior, displaying maleimides with alkyl chains of n = 3 and n = 4 the best antifungal activities in most fungi. Different substituents on the benzene ring did not have a clear influence on the activity. Values of chemical potential properties as well as of energy do not sufficiently discriminate between active and inactive compounds. Nevertheless, it was found that, although log P alone is not strong enough to properly predict the antifungal activity, the comparison of its values for compounds within the same sub-type, showed an enhancement of antifungal activity along with an increment of lipophilicity. In addition, the LUMO's electronic clouds of the highly active compounds showed to be concentrated on the imido ring, indicating that their carbon atoms are potential sites for nucleophilic attack. Same results were obtained from MEPs. Most of the active compounds did not show cytotoxic activity against human cancer cell lines and no one possessed hemolytic activity, indicating that their activity is selective to pathogenic fungi and that they are not toxic at MIC concentrations.
Sortino,Garibotto,Cechinel Filho,Gupta,Enriz,Zacchino
experimental part
p. 2823 - 2834
(2011/06/21)

The non-metathetic role of Grubbs' carbene complexes: From hydrogen-free reduction of α,β-unsaturated alkenes to solid-supported sequential cross-metathesis/reduction
An efficient and high-yielding "hydrogen-free" reduction of α,β-unsaturated alkenes was carried out employing Grubbs' catalyst in a non-metathetic role and Et3SiH. Conditions were optimized under microwave irradiation. Application to the solid-phase organic synthesis allows a facile construction of sp3-sp3 carbon bonds through a sequential cross metathesis/olefin reduction.
Poeylaut-Palena, Andres A.,Testero, Sebastian A.,Mata, Ernesto G.
supporting information; experimental part
p. 1565 - 1567
(2011/03/20)

Synthesis, anti-inflammatory activity and COX-1/COX-2 inhibition of novel substituted cyclic imides. Part 1: Molecular docking study
A group of cyclic imides (1-13) was designed for evaluation as selective COX-2 inhibitors and investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model. Compounds 5b, 6b, 11b, 11c, 12b and 12c were proved to be potent COX-2 inhibitors with IC50 range of 0.1-1.0 μM. In vitro COX-1/COX-2 inhibition structure-activity studies identified compound 5b as a highly potent (IC50 = 0.1 μM), and an extremely selective [COX-2 (SI) = 400] comparable to celecoxib [COX-2 (SI) > 333.3], COX-2 inhibitor that showed superior anti-inflammatory activity (ED 50 = 104 mg/kg) relative to diclofenac (ED50 = 114 mg/kg). A Virtual screening was carried out through docking the designed compounds into the COX-2 binding site to predict if these compounds have analogous binding mode to the COX-2 inhibitors. Molecular modeling (docking) study showed that the CH3O substituents of 5b inserted deep inside the 2°-pocket of the COX-2 active site, where the O-atoms of such group underwent a H-bonding interaction with His90 (2.43, 2.83 ), Arg513 (2.89 ) and Tyr355 (3.34 ). Docking study of the synthesized compound 5b into the active site of COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor.
Abdel-Aziz, Alaa A.-M.,Eltahir, Kamal E.H.,Asiri, Yousif A.
scheme or table
p. 1648 - 1655
(2011/05/06)

Intermolecular oxidative C-N bond formation under metal-free conditions: Control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation
A new synthetic approach toward intermolecular oxidative C-N bond formation of arenes has been developed under transition-metal-free conditions. Complete control of chemoselectivity between aryl sp2 and benzylic sp 3 C-H bond imidation was achieved by the choice of nitrogen sources, representatively being phthalimide and dibenzenesulfonimide, respectively.
Kim, Hyun Jin,Kim, Jiyu,Cho, Seung Hwan,Chang, Sukbok
supporting information; experimental part
p. 16382 - 16385
(2011/12/13)

Metal-free intermolecular oxidative C-N bond formation via tandem C-H and N-H bond functionalization
The development of a novel intermolecular oxidative amination reaction, a synthetic transformation that involves the simultaneous functionalization of both a N-H and C-H bond, is described. The process, which is mediated by an I(III) oxidant and contains no metal catalysts, provides a rapid and green method for synthesizing protected anilines from simple arenes and phthalimide. Mechanistic investigations indicate that the reaction proceeds via nucleophilic attack of the phthalimide on an aromatic radical cation, as opposed to the electrophilic aromatic amination that has been reported for other I(III) amination reactions. The application of this new reaction to the synthesis of a variety of substituted aniline derivatives is demonstrated.
Kantak, Abhishek A.,Potavathri, Shathaverdhan,Barham, Rose A.,Romano, Kaitlyn M.,Deboef, Brenton
supporting information; experimental part
p. 19960 - 19965
(2012/01/13)

N -alkynyl imides (ynimides): Synthesis and use as a variant of highly labile ethynamine
This study describes the first reliable synthesis of N-alkynyl imides (ynimides). This was accomplished with a copper-catalyzed coupling reaction between alkynyl(triaryl)bismuthonium salts and five-membered imides. We also found that it was possible to utilize N-ethynyl phthalimide as a variant of the highly labile ethynamine. 4-Amino-1,2,3-triazole was successfully obtained via the CuAAC reaction of N-ethynyl phthalimide with azide followed by hydrazinolysis of the phthaloyl protecting group.
Sueda, Takuya,Oshima, Ayumi,Teno, Naoki
scheme or table
p. 3996 - 3999
(2011/10/01)

Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore
Several series of compounds containing the 1,4-dioxo-2-butenyl moiety have been prepared as candidate cytotoxins, including the methyl N-arylmaleamates, methyl N-arylfumaramates, and N-arylmaleimides. In addition, the N-arylisomaleimides were synthesized which are the structural isomers of N-arylmaleimides. These compounds were evaluated against human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 cells. Methyl N-arylfumaramates showed the highest cytotoxic potencies and, in particular, methyl N-(3,4-dichlorophenyl)fumaramate is six times more potent than melphalan towards L1210 cells and is equipotent with this drug in the Molt 4/C8 assay. Electrophilicity of compounds under investigation was demonstrated by carrying out thiolation using model benzyl mercaptan on representative compounds. Methyl N-(3,4-dichlorophenyl)fumaramate and methyl N-(4-chlorophenyl)maleamate inhibited human N-myristoyltransferase, a possible molecular target, in high micromolar range. QSAR and molecular modeling revealed some correlations between different structural features of a number of the molecules and cytotoxic potencies. Methyl N-arylfumaramates were well tolerated in mice in comparison to the analogs in other series of compounds tested. The data obtained in this investigation affords guidelines for preparing new series of molecules with greater potencies.
Jha, Amitabh,Mukherjee, Chandrani,Prasad, Ashok K.,Parmar, Virinder S.,Vadaparti, Manjula,Das, Umashankar,De Clercq, Erik,Balzarini, Jan,Stables, James P.,Shrivastav, Anuraag,Sharma, Rajendra K.,Dimmock, Jonathan R.
experimental part
p. 1510 - 1515
(2010/06/16)

Gold-catalyzed halogenation of aromatics by N-halosuccinimides
(Chemical Equation Presented) Golden bromination: A highly efficient and mild AuCl3-catalyzed bromination of aromatic rings with Nbromosuccinimide (NBS) has been developed. This method works with a low catalyst loading (down to 0.01 mol %) and can be combined with transition metal catalyzed transformations to deliver various aryl products.
Mo, Fanyang,Yan, Jerry Mingtao,Qiu, Di,Li, Fei,Zhang, Yan,Wang, Jianbo
body text
p. 2028 - 2032
(2010/06/17)

Solid-phase synthesis of N-aryl succinimides
A new method upon adopting a solid-phase strategy for synthesis of N-aryl succinimides is described here, using the silica-bound benzoyl chloride (SBBC) as dehydrating agent in reaction with N-arylsuccinamic acids. The main advantage of this method is the
Rad-Moghadam, Kurosh,Kheyrkhah, Leila
experimental part
p. 2108 - 2115
(2009/10/17)

Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors
The endocannabinoid 2-arachidonoylglycerol (2-AG) plays a major role in many physiological processes, and its action is quickly terminated via enzymatic hydrolysis catalyzed by monoglyceride lipase (MGL). Regulating its endogenous level could offer therapeutic opportunities; however, few selective MGL inhibitors have been described so far. Here, we describe the synthesis of N-substituted maleimides and their pharmacological evaluation on the recombinant human fatty acid amide hydrolase (FAAH) and on the purified human MGL. A few N-arylmaleimides were previously described (Saario, S. M.; Salo, O. M.; Nevalainen, T.; Poso, A.; Laitinen, J. T.; Jarvinen, T.; Niemi, R. Characterization of the Sulfhydryl-Sensitive Site in the Enzyme Responsible for Hydrolysis of 2-Arachidonoylglycerol in Rat Cerebellar Membranes. Chem. Biol. 2005, 12, 649-656) as MGL inhibitors, and along these lines, we present a new set of maleimide derivatives that showed low micromolar IC50 and high selectivity toward MGL vs FAAH. Then, structure-activity relationships have been investigated and, for instance, 1-biphenyl-4-ylmethylmaleimide inhibits MGL with an IC50 value of 790 nM. Furthermore, rapid dilution experiments reveal that these compounds act as irreversible inhibitors. In conclusion, N-substituted maleimides constitute a promising class of potent and selective MGL inhibitors.
Matuszak, Nicolas,Muccioli, Giulio G.,Labar, Geoffray,Lambert, Didier M.
experimental part
p. 7410 - 7420
(2010/04/30)

Substituent chemical shifts of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides
NMR spectra of a series of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides were examined to estimate the electronic effect of the amide and imide groups on the chemical shifts of the hydrogen and carbon nuclei of the benzene ring.
Lee, Hye Sun,Yu, Ji Sook,Lee, Chang Kiu
scheme or table
p. 711 - 715
(2010/07/05)

Highly enantioselective reduction of the C-C double bond of N-phenyl-2-methyl- and N-phenyl-2,3-dimethyl- maleimides by fungal strains
The C{single bond}C double bond of non-substituted and substituted maleimides were hydrogenated to the corresponding succinimides by fungal strains. 2- and 2,3-methylated-phenyl-maleimides were enantioselectively reduced to (R)-N-phenyl-3-methylsuccinimid
Sortino, Maximiliano A.,Filho, Valdir Cechinel,Zacchino, Susana A.
body text
p. 1106 - 1108
(2009/09/30)

Polyethylene glycol as a nonionic liquid solvent for the synthesis of N-alkyl and N-arylimides
Polyethylene glycol (PEG) an inexpensive, nontoxic, environmentally friendly reaction medium for the synthesis of N-alkyl and N-arylphthalimides to afford the corresponding adducts in excellent yields under mild reaction conditions. The use of PEG avoids the use of acidic or basic catalysts, and moreover PEG could be recovered and reused.
Liang, Jun,Lv, Jing,Fan, Ji-Cai,Shang, Zhi-Cai
experimental part
p. 2822 - 2828
(2009/12/03)

An efficient protocol for the synthesis of N-Alkyl- and N-Arylimides using the lewis acidic ionic liquid choline chloride-2ZnCl2
Lewis acidic ionic liquid choline chloride-2ZnCl2 is shown to be for the first time an excellentmedium and efficient catalyst for the synthesis of N-alkyl- and N-arylimides in good yields under mild conditions.
Xiea, You-Teng,Houb, Rei-Sheu,Wangb, Huey-Min,Kangc, Iou-Jiun,Chena, Ling-Ching
experimental part
p. 839 - 842
(2010/08/13)

Gold and gold-platinum as active and selective catalyst for biomass conversion: Synthesis of γ-butyrolactone and one-pot synthesis of pyrrolidone
It has been found that gold is highly active and selective catalyst for the hydrogenation of succinic anhydride (SAN) to γ-butyrolactone (GBL). Using TiO2 as support and performing the reaction in presence of molecular sieves, it was possible to obtain the highest reaction rate ever obtained with 97% selectivity to GBL at 97% conversion. The process appears to be controlled by H2 dissociation on gold and the catalytic activity can be further improved, without loss of selectivity, by adding a very small amount of Pt (100 ppm) to increase the rate of H2 dissociation. We also found that gold is an efficient catalyst for the one-pot conversion of SAN into pyrrolidone and pyrrolidone derivates.
Budroni, Gerolamo,Corma, Avelino
experimental part
p. 403 - 408
(2009/02/05)