• Title/Summary/Keyword: Mannich

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Organocatalytic Mannich-Type Reactions of Cyclic N-Sulfimines with Trimethylsiloxyfuran and Pyrazolin-5-one

  • Lee, Jiseon;Kim, Sung-Gon
    • Journal of the Korean Chemical Society
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    • v.63 no.5
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    • pp.346-351
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    • 2019
  • Mannich-type reactions of cyclic N-sulfimines with 2-trimethylsiloxyfuran and pyrazolin-5-one have been developed using phosphoric acid (PA) as an organocatalyst. 2-Trimethylsiloxyfuran underwent a vinylogous Mannich-type reaction with cyclic N-sulfimines in the presence of the PA catalyst to give sulfamidate ${\gamma}$-butenolides in good yields and with high diastereoselectivities (up to 90% yield and 7:1 dr). In addition, the reaction between pyrazolin-5-one and a diverse range of cyclic N-sulfimines provided access to sulfamidates in good to high yields (up to 94% yield).

Synthesis of Mannich Bases Using Substitued Aromatic Alcohols with Secondary Amines: Relative Reactivity and Regioselectivity Depending on Substrates (치환된 방향족 알코올과 이차아민을 사용한 Mannich염기의 합성:기질에 따른 상대적인 반응성과 위치선택성)

  • Chi, Ki Whan;Ahn, Yoon Soo;Park, Tae Ho;Ahn, Jeong Soo;Kim, Hyun Ah;Park, Joo Yeon
    • Journal of the Korean Chemical Society
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    • v.45 no.1
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    • pp.51-60
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    • 2001
  • One-pot Mannich reaction of substituted hydroxy aromatic compounds with secondary amines in an aprotic solvent has been studied. The results demonstrate that the relative reactivity and regioselectivity of the Mannich reaction depend on the steric hindrance of amines as well as the nucleophilicity of hydroxy aromatic rings.

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Asymmetric Mannich-type Reactions of Fluorinated Ketoesters with Binaphthyl-Modified Thiourea Catalysts

  • Kang, Young-Ku;Yoon, Sung-Je;Kim, Dae-Young
    • Bulletin of the Korean Chemical Society
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    • v.32 no.4
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    • pp.1195-1200
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    • 2011
  • The catalytic enantioselective Mannich-type reaction promoted by chiral binaphthyl-modified bifunctional organocatalysts is described. The treatment of ${\alpha}$-fluoro-${\beta}$-ketoesters with N-Boc imines under mild reaction conditions afforded the corresponding ${\beta}$-aminated ${\alpha}$-fluoro-${\beta}$-ketoesters with excellent enantioselectivities (up to 98% ee).

Synthesis of Mannich Bases of Antineoplaston A10 and their Antitumor Activity

  • Choi, Bo-Gil;Seo, Hee-Kyoung;Chung, Byung-Ho;Choi, Sang-Un;Lee, Chong-Ock
    • Archives of Pharmacal Research
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    • v.17 no.6
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    • pp.467-469
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    • 1994
  • Some Mannich bases of Antineoplaston A10 which is antitumor agent under chlinical investigation were synthesized and tested fro cytotoxicity. The tested compounds (2a, 2b, 2d) showed good activity comparable to that of carboplatin.

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Intramolecular Oxa-Mannich Reaction of 1,3-Dihydro-2-benzofuran-1-ol for Efficient Synthesis of 1-Aminophthalan Derivatives

  • Kim, Heebum;Kim, Sung-Gon
    • Journal of the Korean Chemical Society
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    • v.66 no.1
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    • pp.9-14
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    • 2022
  • An efficient method for the synthesis of 1-aminophthalans has been developed. The intramolecular oxa-Mannich reaction of 1,3-dihydro-2-benzofuran-1-ols with p-toluenesulfonylamine in the presence of Cs2CO3 as a base, without using any catalyst, provided the desired 1-aminophthalans in moderate to good yields.

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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