• 제목/요약/키워드: Mannich Reaction

검색결과 30건 처리시간 0.021초

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

  • Lee, Jiseon;Kim, Sung-Gon
    • 대한화학회지
    • /
    • 제63권5호
    • /
    • pp.346-351
    • /
    • 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).

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
    • /
    • 제32권4호
    • /
    • pp.1195-1200
    • /
    • 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).

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

  • Kim, Heebum;Kim, Sung-Gon
    • 대한화학회지
    • /
    • 제66권1호
    • /
    • pp.9-14
    • /
    • 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.

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

  • 지기완;안윤수;박태호;안정수;김현아;박주연
    • 대한화학회지
    • /
    • 제45권1호
    • /
    • pp.51-60
    • /
    • 2001
  • 치환된 하이드록시 방향족 화합물과 이차아민, paraformaldehyde를 비 양성자성 용매하에서 one-pot으로 반응시켜 기질에 따른 상대적인 반응성을 비교하였으며, Mannich반응이 일어난 자리도 조사하였다. 치환된 하이드록시 방향족 고리의 Mannich반응의 반응성과 위치선댁성은 기질의 친핵성도와 아민의 입체장애에 의존함을 알 수 있었다.

  • PDF

Carbon-based Solid Acid Catalyzed One-pot Mannich Reaction: A Facile Synthesis of β-Amino Carbonyl Compounds

  • Davoodnia, Abolghasem;Tavakoli-Nishaburi, Afsaneh;Niloofar, Tavakoli-Hoseini
    • Bulletin of the Korean Chemical Society
    • /
    • 제32권2호
    • /
    • pp.635-638
    • /
    • 2011
  • A simple and efficient method for the synthesis of $\beta$-amino carbonyl compounds by one-pot three-component Mannich reaction of acetophenone, aromatic aldehydes and aromatic amines using a carbon-based solid acid (CBSA), as an effective and reusable catalyst, is described. The present methodology offers several advantages such as simple procedure with an easy work-up, shorter reaction times, and high yields.

Polyaniline/SiO2를 이용한 one-pot Mannich 반응: β-amino carbonyl 화합물의 효율적인 합성 (Polyaniline/SiO2 Catalyzed One-pot Mannich Reaction: An Efficient Synthesis of β-amino Carbonyl Compounds)

  • Yelwande, Ajeet A.;Arbad, Balasaheb R.;Lande, Machhindra K.
    • 대한화학회지
    • /
    • 제55권4호
    • /
    • pp.644-649
    • /
    • 2011
  • Polyaniline/$SiO_2$ 촉매를 이용하여, acetophenone, aromatic aldehydes와 aromatic amines을 에탄올 용매 속에서 반응시켜서 다양한 various ${\beta}$-amino ketones을 one-pot mannich 반응을 수행하였으며, 이 반응을 위해 silica가 충진된 여러 가지 종류의 wt% polyaniline을 화학적인 산화방법에 의해 합성하였다. 합성한 촉매는 thermal analysis(TG-DTA), X-ray diffraction (XRD), scanning electron microscopy(SEM) energy dispersive spectroscopy(EDS), 및 Fourier transform infrared spectroscopy (FT-IR) 방법으로 확인하였으며, 촉매의 용매에 대한 안정도 UV-Visible spectroscopy로 측정하였다. Polyaniline/$SiO_2$ 촉매를 이용하는 합성 방법은높은 수율로 얻어지며, work up이 쉽고, 독성이 없으며, 쉽게 회수하여 재사용이 가능하다.