An alumina-catalyzed Michael addition of mercaptans to N -anilinomaleimides and its application to the solution-phase parallel synthesis of libraries

Cheng, Soan; Comer, Daniel D.

doi:10.1016/s0040-4039(01)02401-7

Cited by 43 publications

(11 citation statements)

References 19 publications

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“…Shimadzu FT-IR-8400 used to get the ir spectra. Proton nmr were recorded on Bruker 400MHz spectrometer using acetone-d 6 and CDCl 3 as solvent in UK, Leister University.…”

Section: Methodsmentioning

confidence: 99%

“…For synthesis of β-amino ketones, the Michael addition of nucleophilic compound to α, β-unsaturated carbonyl compounds is convenient rote for the construction of C-C and C-N [3,4,5] bands. These compounds were used as starting materials for the synthesis of different heterocycles [6]. Schiff's bases, (R-CH=N-R1) where R and R1 are alkyl, aryl, cyclo alkyl or heterocyclic group) are products of primary amines with carbonyl compound like β-amino carbonyl compounds [7].…”

Section: Synthesis Of Some New Benzoxazepine Compounds Form Derivativmentioning

confidence: 99%

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Synthesis of Some New Benzoxazepine Compounds Form Derivatives of Schiff Bases

Ahmed¹,

Ahmad²,

Ahmed³

2020

J.Edu.Sci.

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This study involved synthesize (1,3) oxazepine. The step 1 includes the preparation of compound (1), (5-Bromo-2-mercapto-6-(4-methoxyphenyl) pyrimidin-4(3H)-one), by the condensation of anisaldehyde and ethylbromoacetat and thiourea in EtOH. In the step2, chalcones (2-6) have been produced. The reaction of compound (1) with chalcones (2-6) that gives azo Michael adduct (7-11) is made in the third step. Schiff's bases (12-16) were prepared by the reaction ketones (7-11) with 2,4dinitroaniline. Finally preparation of new benzo [1,3] oxazepine compounds (17-21) are prepared by the reaction of phthalic anhydride with Schiff's bases. The synthesized compounds are identified by physical (melting points, colour change) and spectral methods such as (IR, proton-nmr).

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“…Shimadzu FT-IR-8400 used to get the ir spectra. Proton nmr were recorded on Bruker 400MHz spectrometer using acetone-d 6 and CDCl 3 as solvent in UK, Leister University.…”

Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of Some New Benzoxazepine Compounds Form Derivativmentioning

confidence: 99%

Synthesis of Some New Benzoxazepine Compounds Form Derivatives of Schiff Bases

Ahmed¹,

Ahmad²,

Ahmed³

2020

J.Edu.Sci.

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“…Later,t he Cheng group demonstrated an efficient synthesis of 3-sulfanylsubstituted 1-(arylamino)-pyrrolidine-2,5-diones (8) in the presence of alumina by reacting mercaptans 2 with Nanilinomaleimides 7 (Scheme 9). [31] Al ibrary of 200 diverse 3sulfanylsubstituted 1-(arylamino)-pyrrolidine-2,5-diones (8) were successfully synthesized by employing aw ide range of functional groups on both the mercaptan and N-anilinomaleimide substrates. The alumina surfaceacted as aL ewis acid and made the thia-Michael addition reactionp ossible.…”

Section: Acid-catalyzed Thia-michaela Ddition Reactionsmentioning

confidence: 99%

“…and Na + + /H + + -exchange-system inhibitors or calcium-antagonist drugs, as well as in herbicides and pesticides. [57][58][59][60][61][62][63] To wards their synthesis, in 2007, Aly et al reported the first thia-Michael addition reactions of N-aroyl-substituted thioureas 30 with methylp ropiolate (31), (E)-1,4-diphenyl-but-2-ene-1,4-dione (32), and dimethyl but-2-ynedioate (33)a sM ichael acceptors. [56] This synthetic strategy involved using refluxing acetic acid as both ac atalysta nd solvent, and allowed the synthesis of 1,3-thiazinones 34-36 in good-to-excellent yields (Scheme 27).…”

Section: Scheme21 Thia-michael Addition Reaction Mediated By Wet Tctmentioning

confidence: 99%

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

2018

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The thia-Michael addition reactionh as been demonstrated to be ah ighly powerful tool in organic synthesis. Indeed, the influential natureo ft his reactionh as been wellestablished in the fields of medicinal chemistry,c atalysis, drug discovery,a nd materials science. The emergence of numerous synthetic strategies that take advantage of thia-Michael addition reactions of electron-deficienta lkenes has unleashed countless opportunities for the design and synthesis of diverse biologically relevant organosulfurc ompounds. However,d espite myriad potential synthetic applications, there has not been anye xclusive reviewso ft he thia-Michael addition reaction. Therefore, this Focus Review plots the journeyo ft he thia-Michael addition reaction in organic synthesis, and is categorized according to catalyzed and catalyst-free thia-Michael addition reactions. Figure 1. Summary of the applicationsoft hia-Michael adducts.[a] Dr.Scheme1.Catalyzed pathways for the thia-Michael addition reaction.EW-G = electron-withdrawing group.Scheme2.Acetic-acid-catalyzed thia-Michael additionr eaction proposed by Allen et al. [24] AsianJ.O rg.Scheme3.Indium-bromide-catalyzed thia-Michael addition reaction.Scheme4.Thia-Michael addition reaction followed by a1 ,2-addition of TMSCN in one pot. TMSCN = trimethylsilyl cyanide.Scheme5.Bi III -catalyzedt hia-Michael additionreactiono fa,b-unsaturated carbonyl compounds. Tf = trifluoromethanesulfonyl.Scheme6.Bismuth-triflate-catalyzed synthesis of bis-thioether compounds. Bn = benzyl.Scheme7.Iron-/copper-catalyzed thia-Michael additionr eaction.Scheme8.VO(OTf) 2 -mediated synthesis of b-mercapto ketones. Np = naphthyl.Scheme9.Substrate scope for the synthesis of 3-sulfanyl-substituted 1-(arylamino)-pyrrolidine-2,5-diones.Scheme10. Regio-and enantioselective addition at the d position of conjugated systems.Scheme11. Mechanistic modelf or the enantioselective d addition of at hiol to an a,b,g,d-unsaturated dienone,catalyzed by achiral Fe III Àsalenc omplex.Scheme12. Chemoselectivesynthesis of 2-amino-3,1-benzothiazines (15) and 3,4-dihydroquinazoline-2-thiones (16)byu sing ortho-aminocinnamate (13)a nd isothiocyanates 14.Scheme13. Reactionmechanism for the chemoselective synthesis of 2amino-3,1-benzothiazines (15)and 3,4-dihydroquinazoline-2-thiones (16).Scheme14. ZrCl 4 -assisted three-component reactionf or the synthesiso fbaryl-b-mercapto ketones.Scheme15. LiF-nanocube-mediated thia-Michael addition reaction.Scheme57. Ni II -catalyzed enantioselective synthesiso f2-aryl-3-nitrothiochroman-4-ols.Scheme58. Te ntative reaction mechanism for the Ni II -catalyzed asymmetric synthesis of 2-aryl-3-nitrothiochroman-4-ols.Scheme59. Pepsin-catalyzed synthesis of functionalized chiral dihydrothiophenes.Scheme69. Mechanistic aspects of the stereoselectives ynthesis of tetrahydrothioxanthenones.Scheme70. Enantioselectivesynthesis of methyl 2-((R)-2-nitro-1-(aryl/heteroaryl)ethylthio)acetatesa nd thiomorpholin-3-ones.Scheme71. Water-accelerated thia-Michael additionr eaction proposedb y Chakraborti and co-work...

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“…Thiol nucleophilic reagents are also known to show chemical reactivity toward chalcones, chalcon epoxides, chalcone dibromides, and their corresponding propynones. Conjugate addition of sulfur-centered nucleophiles to a,b-unsaturated carbonyls such as chalcones serves as a powerful synthetic method in this area of sulfur chemistry (Garg et al, 2005;Sasai et al, 1995;Lee et al, 2001;Cheng and Cromer, 2002).…”

Section: Introductionmentioning

confidence: 99%

The synthesis and screening of the antimicrobial activity of some novel 3-(furan-2-yl)-1-(aryl)-3-(phenylthio) propan-1-one derivatives

et al. 2010

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A series of thiophenol adducts (3a-m) were prepared by addition of thiophenol to chalcones (1a-m) in the presence of a catalytic amount of KOt-Bu in solvent free conditions. In addition, the antibacterial and antifungal in vitro properties were tested against some human pathogenic microorganisms by employing the disk diffusion technique. A majority of compounds were remarkably active against several of the microorganisms. Compound 3i was determined to be the most active compound.

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An alumina-catalyzed Michael addition of mercaptans to N -anilinomaleimides and its application to the solution-phase parallel synthesis of libraries

Cited by 43 publications

References 19 publications

Synthesis of Some New Benzoxazepine Compounds Form Derivatives of Schiff Bases

Synthesis of Some New Benzoxazepine Compounds Form Derivatives of Schiff Bases

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

The synthesis and screening of the antimicrobial activity of some novel 3-(furan-2-yl)-1-(aryl)-3-(phenylthio) propan-1-one derivatives

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