• Title/Summary/Keyword: Mannich

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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.

Synthesis of Mannich Base of Benzoxazolin-2-thione and Alkyl Ester of PAS and Their Antimicrobial Activities (Benzoxazolin-2-thione과 PAS의 Alkyl Ester과의 Mannich Base 합성 및 항균력에 관한 연구)

  • 정원근;정상헌;정필근;윤원영;이남복
    • YAKHAK HOEJI
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    • v.18 no.4
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    • pp.243-248
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    • 1974
  • Nine benzoxazolin-2-thione derivatives were sunthesized as the potential antimicrobial substances. These compounds were tested for the antimicrobial activities using Staphylococcus aureus and Escherichia coli by way of tube dilution method. The three compounds of I, II and VII omjoboted the growth of S.aureus at the concentration of 1${\mu}$g/ml, and III,VI,VIII and IX exhibited considerable antimicrobial activities against S. aureus at the concentration of 10.m.u.g/ml. As to the growth of E. Coli, VII VII and VIII inhibited at the concentration of 1${\mu}$g/,l. II,III and IV exhibited considerable antimicrobial activities against E. coli at the concentration of 10${\mu}$g/ml.

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Studies on the synthesis of mannish bases of 2,2'-methylene bis(3,4,6-trichlorophenoxyacetic acid) and their antimicrobial activities (2,2'-methylene bis(3,4,6-trichlorophenoxyacetic acid)의 mannich bases합성및 항균작용에 관한 연구)

  • 김종호
    • YAKHAK HOEJI
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    • v.16 no.2
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    • pp.97-107
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    • 1972
  • Thirty-three Mannich bases of 2,2'-methylene bis(3,4,6-trichlorophenoxyacetic acid) were synthesized as potential antimicrobial agents and tested against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Trichophyton rubrum, Microsporum gypseum, Epidermophyton floccosum, Aspergillus niger and Aspergillus oryzae in vitro. It was found that: 1) Compounds 24 and 22 were active against Staphylococcus aureus and Bacillus subtilis at the concn. of 1 $\mu$g/ml respectively; 2) Compounds 9 and 29 were active against Trichophyton rubrum at the concn. of 2 $\mu$g/ml respectively; 3) Compouns 9 and 30 were active against Microsporum gypseum at the concn. of 2 $\mu$g/ml respectively; 4) Compounds 6,9,13,15,21,28,29,31,33 and 34 were active against Epidermophyton floccosum at the concn. of 1 $\mu$g/ml respectively; 5) Compounds 6,9,18 and 28 were active against Aspergillus niger and Aspergillus oryzae at the concn. of 1 $\mu$g/ml respectively.

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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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Syntheses and antimicrobial and antitumor activities of isatin derivatives

  • Chough, Yun-Sung;Kang, Kun-Il
    • YAKHAK HOEJI
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    • v.17 no.3
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    • pp.141-146
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    • 1973
  • Eight isatin N-Mannich bases were synthesized and tested their antimicrobial and antitumor activities. N-Piperidinomethylisatin-(N-cyclohexyl)-thiosemicarbazone is active against St. aureus at 10${\mu}$g/disk and isatin thiosemicarbazone against P. chrysogenum at 10${\mu}$g disk.

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