• Title/Summary/Keyword: Imine synthesis

Search Result 41, Processing Time 0.021 seconds

The Synthesis of 2-Methyl-5,5'-gem-Disubstituted-${\Delta}^2$-Thiazolines (2-Methyl-5,5'-gem-Disubstituted-${\Delta}^2$-Thiazoline系 化合物의 合成)

  • Chi Sun Hahn
    • Journal of the Korean Chemical Society
    • /
    • v.7 no.4
    • /
    • pp.230-237
    • /
    • 1963
  • The synthesis of 2-methyl-5,5'-gem-disubstituted-$\Delta^2$-thiazolines has been undertaken by two methods. The first involves the preparation of gem-disubstituted N-or S-acetylamino mercaptan intermediates by ring opening of the corresponding thiiranes with ammonia. The second consists of the ring opening of gem-disubstituted ethylene imines using thiolacetic acid. The thiirane rings have never been opened under conditions as vigorous as that of using sodium amide in liquid ammonia. This is probably due to retardation by the gem-disubstituents. In contrast to this, the corresponding ethylene imine ring opens easily, in spite of the same stereochemical situation. The stabilization of gem-disubstituted cyclic compounds has been discussed from a stereochemical point of view. It has been concluded from the results of this work that the compression effect of gem-disubstitution is not due to bond angle deformation, which was observed by Thorpe and Ingold, but mostly to an electronic bond interaction of the gem-disubstituents and to the hetero atom(s), if any.

  • PDF

Synthesis of N-methylspiro [1,2,3,4-tetrahydro-naphthalene-1,2'-pyrrolidine]

  • Jang, Jin-Hee;Sin, Kwan-Seog;Park, Hae-Il
    • Proceedings of the PSK Conference
    • /
    • 2003.04a
    • /
    • pp.237.2-237.2
    • /
    • 2003
  • A pathway for synthesis of N-methylspiro [1,2,3,4-tetrahydro-naphthalene-1,2'- pyrrolidine] was developed. Formation of the imine compound from ${\alpha}$-tetralone and methylamine using titanium tetrachloride followed by ddition of allylmagnesium bromide gave (1-allyl-1,2,3,4-tetrahydro-naphthalen-1-yl)methylamine. (omitted)

  • PDF

Synthesis of Pyrimidines and Heteroannulated Pyrimidine Ring Systems (Pyrimidines과 pyrimidine의 헤테로고리의 합성)

  • Mohammed, F.K.;Badrey, M.G.
    • Journal of the Korean Chemical Society
    • /
    • v.55 no.2
    • /
    • pp.218-229
    • /
    • 2011
  • We have involved the imine compound 1 in condensations with various nitrogenous reagents including hydrazine hydrate to construct differently substituted pyrimidines. One of the pyrimidines so obtained was further subjected to interactions with different reagents such as propionic acid, formic acid, ethyl chloroformate, acdetic anhydride, carbon disulphide, cyanogene bromide, triflauroacetic acid and ethyl chloroacetate which resulted in the formation of annulated heterocyclic systems as pairs of isomers in most cases as a result of Dimroth-type rearrangement.

Synthesis, Spectral Characterization, Electron Microscopic Study and Influence on the Thermal Stability of Phosphorus-containing Dendrimer with a 4,4'-Sulphonyldiphenol at the Core

  • Dadapeer, Echchukattula;Rasheed, Syed;Raju, Chamarthi Naga
    • Bulletin of the Korean Chemical Society
    • /
    • v.32 no.2
    • /
    • pp.498-502
    • /
    • 2011
  • The divergent synthesis of novel phosphorus-containing dendrimer with 4,4'-sulphonyldiphenol at the core has been accomplished involving simple condensation reactions using $P(O)Cl_3$, $P(S)Cl_3$, 3-amino-phenol, 3-hydroxy-benzaldehyde, and 2-butyn 1, 4-diol. The final compound was a Schiff's base macromolecule possessing 4 imine bonds, 8 acetylenic bonds and 8 OH groups at the periphery. The structures of intermediate compounds were confirmed by IR, NMR ($^1H$, $^{13}C$ and $^{31}P$), LC-Mass and C, H, N analysis. The structure of the final dendrimer (5) was confirmed by IR, NMR ($^1H$, $^{13}C$ and $^{31}P$), MALDI-TOF-MS, and C, H, N analysis. The surface morphological characteristics of the final dendrimer were understood by Scanning Electronic Microscopic study (SEM). The thermal stability of the final dendrimer was studied by TGA/DTA analysis.

Synthesis and Identification of Novel Pyrazoline and Its Anti-cancer Property (새로운 피라졸린 화합물의 합성과 구조결정 및 항암효과)

  • Koh, Dong-Soo
    • Journal of Applied Biological Chemistry
    • /
    • v.54 no.2
    • /
    • pp.143-146
    • /
    • 2011
  • Novel pyrazoline (4) was synthesized from chalcone (3) which was prepared from 2'-hydroxy-l'acetonaphthone (1) and 4-methoxy benzaldehyde (2). Pyrazoline (4) forms resonance assisted hydrogen bond between naphthol hydroxyl group and imine nitrogen in a pyrazoline ring. Pyrazoline (4) shows Poly ADP-ribose Polymerase (PARP) cleavage ability as a proof of apoptosis in cancer cell, which reveals its anti-cancer property.

An Efficient Synthesis of Substituted Quinolines via Indium(III) Chloride Catalyzed Reaction of Imines with Alkynes

  • Zhu, Mei;Fu, Weijun;Xun, Chen;Zou, Guanglong
    • Bulletin of the Korean Chemical Society
    • /
    • v.33 no.1
    • /
    • pp.43-47
    • /
    • 2012
  • An efficient synthetic method for the preparation of quinolines through indium(III) chloride-catalyzed tandem addition-cyclization-oxidation reactions of imines with alkynes was developed. The processes can provide a diverse range of quinoline derivatives in good yields from simple imines and alkynes.

Total synthesis of Antofine by using Intramolecular 1.3-dipolar cycloaddition of Azidealkene

  • Lee, Jae-Kwang;Lee, Tae-Ho;Song , So-Young
    • Proceedings of the PSK Conference
    • /
    • 2002.10a
    • /
    • pp.362.2-362.2
    • /
    • 2002
  • Antofine belongs to the Phenathroindolizidine group of alkaloids. This natural products exhibit interesting biological properties such as antitumour activity. and anti-inflammentory. Wittig reaction of phenathrenealdehyde with the phosponium salt provided the phenathreneazidealkene in good yield. Intramolecular 1.3-dipolar cycloaddition of the resulting azidealkent in refluxing benzene proceeded the imine. It was reduced with cyanoborohydride of Noyori's Asymmetric Hydrogenation. (omitted)

  • PDF