• Title/Summary/Keyword: Mannich Reaction

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Mannich-type Reactions of in Situ Generated N-Acyliminium Ions from α-Amido p-Tolylsulfones with Silyl Enolates

  • Lee, Sang-Hyeup;Kadam, Santosh T.
    • Bulletin of the Korean Chemical Society
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    • v.32 no.10
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    • pp.3738-3742
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    • 2011
  • Bismuth tribromide ($BiBr_3$) catalyzed Mannich-type reactions of N-acyliminium ions which generated in situ from N-benzyloxycarbonylamino p-tolylsulfones have been developed. In the presence of catalytic amount of $BiBr_3$, N-benzyloxycarbonylamino p-tolylsulfones prepared from aromatic and aliphatic aldehydes reacted with silyl enol ether and silyl enol ester under mild reaction conditions to afford N-Cbz-protected ${\beta}$-amino ketones and N-Cbz-protected ${\beta}$-amino esters in moderate to good yield, respectively.

Applications of Cross-linked Poly(4-vinylpyridine/styrene) Copolymer supported Ytterbium(III) Triflate in Mannich-type Reaction:Three Component One-pot Synthesis of β-Aminoketones

  • Lee, Sang-Hyeup;Lee, Byoung-Se
    • Bulletin of the Korean Chemical Society
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    • v.30 no.3
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    • pp.551-555
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    • 2009
  • The ytterbium catalyst immobilized on the cross-linked poly(4-vinylpyridine/styrene) copolymer (P/S-Yb) was applied in the Mannich-type, three component one-pot synthesis of $\beta$-aminoketones. This catalytic system showed excellent catalytic activity and selectivity which resulted in the exclusive formation of $\beta$-aminoketone. The applicability of this immobilized catalyst system was shown by the reusability test and again highlighted by the synthesis of a $\beta$-aminoketone library using a broad range of substrates.

Synthesis and Antihypertensive Activity of Certain Mannish Bases of 2- Ethoxycarbonylindoles and 5H-Pyridazino [4,5-b] indoles

  • El Gendy, Adel A.;El Banna, Hosny A.
    • Archives of Pharmacal Research
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    • v.24 no.1
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    • pp.21-26
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    • 2001
  • This manuscript reports the synthesis of two series of Mannich Bases 3-12 and 21-40 obtained respectively by the reaction of either 2- ethoxycarbonylindoles 1-2 or 5H-pyridazino [4,5-b]indoles 17-20 as a substrate with formalin and the appropriate $2^{\circ}C$amines under the suitable Mannich conditions. fourteen of the synthesized Mannich basese were screened as antihypetensive agents in normotensive anesthetized rats. The effect of compound 4 in normotensive anesthetized dogs was also studied.

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Highly Selective Synthesis of β-Amino Carbonyl Compounds over ZSM-5-SO3H under Solvent-free Conditions

  • Massah, Ahmad Reza;Kalbasi, Roozbeh Javad;Samah, Neda
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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    • pp.1703-1708
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    • 2011
  • ZSM-5-$SO_3H$ efficiently catalyzed the one-pot three-component Mannich reaction of aldehydes, anilines, and ketones. ${\beta}$-Aminocarbonyl compounds were obtained in reasonable yields and excellent stereoselectivities when the reaction was carried out at room temperature under solvent-free conditions. Simple experimental conditions and product isolation procedure makes this protocol potential for the development of clean and environment-friendly strategy for the synthesis of ${\beta}$-amino-ketones. The catalyst was recovered and reused for subsequent runs.

Synthesis of Azabicyclo[3.2.1]octane Skeleton of Tropane Alkaloid (트로판 알칼로이드의 아자비시크로[3.2.1]옥탄 골격합성)

  • Suh, Young-Ger;Choi, Young-Gi;Jung, Jae-Kyung;Min, Kyung-Hoon
    • YAKHAK HOEJI
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    • v.41 no.1
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    • pp.18-21
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    • 1997
  • Synthesis of an optically active azabicyclo[3.2.1]octane skeleton as a backbone of the tropane alkaloids has been achieved by employing intramolecular Mannich reaction. Utilizat ion of (R)-${\alpha}$-methylbenzylamine as a chiral auxiliary provided an excellent cyclization of amino dioxolane precursor. However, this auxiliary did not afford high asymmertic induction for the preparation of the optically active cyclization precursor.

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Oxazole, Pyrazole and Piperidine Derivatives Having an o-Hydroxy-aryl Moirty with Anticipated Molluscicidal Activity

  • Nawwar, Galal-A.M.;Swellem, Randa-H.;Ibrahim, Amal-M
    • Archives of Pharmacal Research
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    • v.17 no.2
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    • pp.66-70
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    • 1994
  • The condensation reactions of hippuric acid and tis furyl derivative with salicyladehydes or that of salicylhippuric acid analogues with furadehyde led to the comesponding oxazoles. These wre subsequently treated with hydrazine hydrate, hydroxylamine or subjected to alkaline hydrolysis to yield new o-hydroxyaryl or salicyl containing derivatives. 5-Substituted salicylanilides were treated with piperidine and formaldehyde in a Mannich type reaction affording the corresponding 3-(N-piperidinomethyl) salicylanilides. It was noticed that the presence of an electron donating group in in position 3 in the salicylanilide moiety decrease the mollusicidal activity.

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Synthesis and Biological Activities of Novel Arylazopyrazolones Substituted with Thiazolyhydrazone

  • Shah, Purvesh J.
    • Journal of the Korean Chemical Society
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    • v.58 no.1
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    • pp.57-61
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    • 2014
  • The 4-(1H)-benzotriazoyl methyl amino benzoate 3 was prepared by Mannich reaction of benzotriazole 1, ethyl-paminobenzoate 2 and formaldehyde. The prepared compound 3 then react with hydrazine hydrate results in the 4-(1H)-benzotriazoyl methyl amino benzoyl hydrazide 4. This compound on condensation with pre-prepared different ethyl 2-(2-(4-(4-substituted phenyl)thiazol-2-yl)hydrazono)-3-oxobutanoates 6a-d, furnished 1-(4-((1H-benzo[d] [1,2,3] triazol-1-yl)methyl amino) benzoyl)-4-(2-(4-(4-substituted phenyl)thiazol-2-yl) hydrazono)-3-methyl-1H-pyrazol-5(4H)-one 7a-d. All the compounds 7a-d was characterized by spectral studies. The compounds showed significant antimicrobial activity against various bacteria and fungi.

Studies on Nitroaniline derivative of 2, 2'-methylene-bis-(3, 4, 6-trichloroacetoxy benzene by Mannich reaction Part I. Synthesis and Antimicrobial activity (2, 2'-methylene-bis-(3, 4, 6-trichloroacetoxy benzene)의 nitroaniline 계 mannich bases에 관한 연구 I. 합성 및 항균성)

  • Yu, Ju-Hyun;Kim, Yu-Sam;Kim, Jong-Ho;Yang, Ryung
    • Korean Journal of Food Science and Technology
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    • v.6 no.1
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    • pp.6-11
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    • 1974
  • Four new compounds; 2,2'-methylene-bis [3, 4, 6-trichloro ${{\beta}-(o-nitroanilino)$ propionoxy} benzene]; m.p. $200{\sim}202^{\circ}C,\;C_{31}H_{22}O_8N_4Cl_6$ 2,2'-methylene-bis [3, 4, 6-trichloro ${{\beta}-(p-nitroanilino)$ propionoxy} benzene]; m.p. $168-170^{\circ}C,\;C_{31}H_{22}O_8N_4Cl_6$ : 2,2'-Methylene-bis [3, 4, 6-trichloro ${{\beta}-(o-chloro-p-nitroanilino)$ propionoxy} benzene]; m.p. $170.5-172.5^{\circ}C,\;C_{31}H_{20}O_8N_4Cl_8$ : 2,2'-Methylene-bis [3, 4, 6-trichloro ${{\beta}-(c-methyl-p-nitroanilino)$ propionoxy} benzene]; m.p. $163-164^{\circ}C,\;C_{33}H_{26}O_8N_4Cl_6$-were synthesized by Mannich reaction from 2,2'-Methylene-bis (3, 4, 6-trichloroacetoxy benzene) and their antimicrobial activities against the microorganisms Staphylococcus aureus, Escherichia coli, Bacillus subtilis Natto, Brevibacterium ammoniagenes, Candida tropicalis, Rhodotorula glutinis, Pseudomonas ovalis, Aspergillus candidus Link, Aspergillus awamori Nakazawa. Aspergillus niger var. Tieghem, Aspergillus usami Sakakuchi, Penicillium notatum-were tested. 2,2'-methylene-bis [3, 4, 6-trichloro ${{\beta}-(o-nitroanilino)$ propionoxy} benzene] showed a strong antimicrobial activity against Bacilus subtilis Natto and Brevibacterium ammoniagenes.

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Synthesis of 2,5Bis(2'-piperidymethyl)piperidine and Related Compounds

  • Hammouda, Metwally;Kandeel, Ex-el-Din;Hamama, Wafaa;Afsah, Elsayed
    • Archives of Pharmacal Research
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    • v.16 no.1
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    • pp.68-70
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    • 1993
  • The triketones 3-6 were obtained by alkylation of cyclopentanone or cyclohexanone with the appropriate cycloalkanone bis-mannich base (1) or (2). Schmidt reaction of the tricketones 3-6 afforded the corresponding trcyclic lactames 7-10 respectively. reduction of 7 and 9 gave compounds 11 and 12 respectively.

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