• 제목/요약/키워드: one-pot synthesis

검색결과 222건 처리시간 0.028초

Syntheses and Characterizations of Lactam Cyclophanes. Attempted Synthesis of a Lactam Catenane Using Hydrogen Bonds

  • 주경미;임혜재;백경수
    • Bulletin of the Korean Chemical Society
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    • 제16권11호
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    • pp.1079-1084
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    • 1995
  • New cyclophanes having multilactam linkages were synthesized and characterized. One-pot coupling reaction of 2,6-pyridinedicarbonyl dichloride and a diamine gave a tetralactam, a hexalactam, and a octalactam in good yields. The TLC behaviour, the molecular symmetry shown by 1H NMR spectrum, and the fragmentation patterns shown by FAB mass spectrum of the octalactam support its monocyclic structure.

Stereoselective Total Synthesis of (-)-Cytoxazone

  • Kim, Ji-Duck;Hoon, Jung-Young
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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    • pp.179.2-179.2
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    • 2003
  • We have developed the novel one-pot synthetic method for regioselective and stereoselective N-protected amines through the reaction of various ethers with chlorosulfonyl isocyanate (CSI). Also, we found a novel technique to compare directly the stability of carbocations in the solution phase and established the stability order of the various carbocations. And we reported the cleavage of benzyl and p-methoxybenzyl protecting groups of alcohols and phenols in the presence of other functional groups using CSI. (omitted)

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Synthesis of Curcumin Glycosides with Enhanced Anticancer Properties Using One-Pot Multienzyme Glycosylation Technique

  • Gurung, Rit Bahadur;Gong, So Youn;Dhakal, Dipesh;Le, Tuoi Thi;Jung, Na Rae;Jung, Hye Jin;Oh, Tae Jin;Sohng, Jae Kyung
    • Journal of Microbiology and Biotechnology
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    • 제27권9호
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    • pp.1639-1648
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    • 2017
  • Curcumin is a natural polyphenolic compound, widely acclaimed for its antioxidant, anti-inflammatory, antibacterial, and anticancerous properties. However, its use has been limited due to its low-aqueous solubility and poor bioavailability, rapid clearance, and low cellular uptake. In order to assess the effect of glycosylation on the pharmacological properties of curcumin, one-pot multienzyme (OPME) chemoenzymatic glycosylation reactions with UDP-${\alpha}-{\text\tiny{D}}$-glucose or UDP-${\alpha}-{\text\tiny{D}}$-2-deoxyglucose as donor substrate were employed. The result indicated significant conversion of curcumin to its glycosylated derivatives: curcumin 4'-O-${\beta}$-glucoside, curcumin 4',4"-di-O-${\beta}$-glucoside, curcumin 4'-O-${\beta}$-2-deoxyglucoside, and curcumin 4',4"-di-O-${\beta}$-2-deoxyglucoside. The products were characterized by ultra-fast performance liquid chromatography, high-resolution quadruple-time-of-flight electrospray ionization-mass spectrometry, and NMR analyses. All the products showed improved water solubility and comparable antibacterial activities. Additionally, the curcumin 4'-O-${\beta}$-glucoside and curcumin 4'-O-${\beta}$-2-deoxyglucoside showed enhanced anticancer activities compared with the parent aglycone and diglycoside derivatives. This result indicates that glycosylation can be an effective approach for enhancing the pharmaceutical properties of different natural products, such as curcumin.

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
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    • 제45권1호
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    • pp.51-60
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    • 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.

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Synthesis of N-Alkylated 4-Fluoro-5-phenylpyrrole-2-carboxylate via Isolable Pyrroline Ionic Intermediates

  • Kim, Sung-Kwan;Jun, Chang-Soo;Kwak, Kyung-Chell;Park, Kwang-Yong;Chai, Kyu-Yun
    • Bulletin of the Korean Chemical Society
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    • 제28권12호
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    • pp.2324-2328
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    • 2007
  • Organic fluorine chemistry produces many useful products. This paper elucidates the reaction of ethyl-4,4- difluoro-2-iodo-5-oxo-5-phenylpentanoate (2) with primary amines in a one-pot scheme. The reaction produced a series of β-fluoropyrrole derivatives at ambient temperatures. In this reaction, the less bulky the primary amine the higher was the resultant yield. When (2) and aqueous methylamine (40%) were allowed to react below 0 oC, 5-(ethoxycarboxyl)-1-methyl-3,3-difluoro-2-hydroxy-2-phenylpyrrolidine, an intermediate molecule for 2-ethyl-4-flouro-1-methyl-5-phenylpyrrole-2-carboxylate (5), was isolated first. Then, (5) reacted with hydroperchloric acid and acetic anhydride to form 5-(ethoxycarboxyl)-1-methyl-3,3-difluoro-2- phenylpyrrolinium perchlorate (6), which was converted to 2-ethyl-4-flouro-1-methyl-5-phenylpyrrole-2- carboxylate gradually in the presence of a base. Our experiments demonstrate that the formation of 2-ethyl-4- flouro-1-methyl-5-phenylpyrrole-2-carboxylate occurs via both one-pot schemes and stepwise pathways, depending on the reaction conditions. The isolation and characterization of the isolated intermediate (6) suggest an anionic pathway for this reaction.

Synthesis of 2-n-Butyl-3-fluoropyrrole Derivatives

  • Kim, Bo-Mi;San, Quan-Ze;Bhatt, Lok Ranjan;Jung, Dong-Woon;Lee, Young-Hang;Chai, Kyu-Yun
    • Bulletin of the Korean Chemical Society
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    • 제30권6호
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    • pp.1293-1296
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    • 2009
  • A new series of N-substituted 2-n-butyl-3-fluoropyrroles were prepared by a simple one-pot reaction designed of retrosynthesis. $\alpha,\alpha-Difluoro-\gamma-iodo-\gamma$-(trimethylsilyl)propyl n-butyl ketone, a component precursor molecule to 2-n-butyl-3-fluoropyrroles, was prepared with Cu(0) catalyst. It reacted with various primary amines to yield N-substituted 2-n-butyl-3-fluoropyrroles. The products were synthesized via a one-pot reaction scheme between $\alpha,\alpha-Difluoro-\gamma-iodo-\gamma$-(trimethylsilyl) propyl n-butyl ketone and primary amines in excess ( $\geq$ 5 molar equivalence), which eliminate the need of KF required in obtaining n-butyl-1H-3-fluoropyrrole. The yield of products depended reversely on spatial bulkness around N-binding carbon.

One-Pot 합성공정으로 만든 Aluminum이 doping된 폴리카보실란으로부터 제조된 치밀한 결정화 탄화규소 섬유 (Dense Polycrystalline SiC Fiber Derived from Aluminum-doped Polycarbosilane by One-Pot Synthesis)

  • 신동근;공은배;류도형;김영희;박홍식;김현이
    • 한국세라믹학회지
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    • 제44권7호
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    • pp.393-402
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    • 2007
  • Polyaluminocarbosilane was synthesized by direct reaction of polydimethylsilane with aluminum(III)-acetylacetonate in the presence of zeolite catalyst. A fraction of higher molecular weight polycarbosilane was formed due to the binding of aluminium acetylacetonate radicals with the polycarbosilane backbone. Small amount of Si-O-Si bond was observed in the as-prepared polyaluminocarbosilane as the result. Polyaluminocarbosilane fiber was obtained through a melt spinning and was pyrolyzed and sintered into SiC fiber from $1200{\sim}2000^{\circ}C$ under a controlled atmosphere. The nucleation and growth of ${\beta}-SiC$ grains between $1400{\sim}1600^{\circ}C$ are accompanied with nano pores formation and residual carbon generation. Above $1800^{\circ}C$, SiC fiber could be sintered to give a fully crystallized ${\beta}-SiC$ with some ${\alpha}-SiC$.

Efficient One-Pot Three-Component Synthesis of Monomethine Cyanine Dyes with Quinoline Nucleus and Their Spectral Properties

  • Fu, Y.L.;Zhang, B.R.;Wang, S.;Gao, X.X.;Wang, L.Y.
    • Bulletin of the Korean Chemical Society
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    • 제34권2호
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    • pp.489-494
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    • 2013
  • An improved method for the preparation of monomethine cyanine dyes with quinoline nucleus by one-pot three-component using 1-methyl-2-quinolinethione, quaternized 2- or 4-methylheterocyclic compounds and methyl p-toluenesulfonate as starting materials was described. Compared with the traditional methods, the new synthetic method reduced the reaction steps, shortened the reaction time, avoided the separation and purification of the intermediate and reduced cost. The dyes absorbed in the region 478.0-563.0 nm and had molar extinction coefficients of $1.3{\times}10^4-9.4 {\times}10^4L\;mol^{-1}\;cm^{-1}$. Their fluorescence maxima and Stokes shifts were in the range of 525.2-594.4 nm and 16.2-80.6 nm in different solvents, respectively. From the spectral properties of the dyes in different solvents, it could be found that the ${\lambda}_{max}$ of the dyes were shorter in protonic solvents, and showed hypsochromic shifts with the increase of polarity of the solvents.

솔잎 추출물이 삽입된 마그네슘-층상규산염 샌드위치 나노입자의 합성과 피부 상재균에 대한 항균 특성에 관한 연구 (Study on Synthesis of Pine Leaf Extract Intercalated Mg-Phyllosilicate Sandwich Nanoparticles and Antimicrobial Activity against Cutaneous Microorganisms)

  • 김성열;최유성
    • 공업화학
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    • 제30권2호
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    • pp.254-259
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    • 2019
  • 본 연구에서는 마그네슘-층상규산염(MgP) 층간에 솔잎 추출물(PLE)이 삽입되어 겹겹이 쌓여있는 샌드위치 구조의 나노입자(PLE/MgP)를 one-pot으로 합성하였다. XRD 분석을 통해 팔면체와 사면체 구조로 MgP가 성공적으로 합성되었으며, PLE가 층간에 삽입되어 MgP 간의 층간거리(d-spacing)가 벌어진 것을 확인하였다. HR-TEM을 통해 모폴로지 변화를 관찰하였으며, 열중량분석법을 통해 PLE가 MgP 대비 10%까지 함유된 것을 확인하였다. 최소저해농도(MIC) 및 최소 사멸농도(MBC) 분석을 통해 피부 상재균에 대한 항균 활성을 검토한 결과 MgP 또는 PLE보다 PLE/MgP의 항균 활성이 더욱 향상된 것을 확인하였다. 이러한 결과는 본 연구에서 개발한 PLE/MgP 유/무기 복합 소재가 화장품 소재, 의료용 소재 등의 다양한 분야에 적용 가능함을 확인하였다.

Total Synthesis of a Norneolignan from Ratanhia Radix

  • Choi, Hong-Daei;Seo, Pil-Ja;Son, Byeng-Wha
    • Archives of Pharmacal Research
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    • 제25권6호
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    • pp.786-789
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    • 2002
  • The total synthesis of a norneolignan isolated from Ratanhia, 5-(3-hydroxypropyl)-2-(2'-methoxy-4'-hydroxyphenyl)benzofuran (8), is described. The key steps contain the one-pot reaction for a 2-arylbenzofuran 6 from methyl 3-(4-hydroxyphenyl)propionate with 2-chloro-2-methylthio-(2'-methoxy-4'-acetoxy)acetophenone (5) in the presence of $ZnCl_2$, and reductive desulfurization of the resulting product 6.