YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Multicyclization Reaction of 2,3-Dichloro-1,4-Naphthoquinone

2,3-디클로로-1,4-나프토퀴논의 다중고리화 반응

  • 김순옥 (성신여자대학교 자연과학대학 화학과) ;
  • 박재경 (성신여자대학교 자연과학대학 화학과) ;
  • 홍사미 (성신여자대학교 자연과학대학 화학과)
  • Published : 1995.04.01
Download PDF
⟨ Previous Next ⟩

Abstract

Aliphatic & aromatic compounds with two nucleophilic functional groups which were chosen as nucleophiles reacted with 2,3-dichloro-1,4-naphthoquinone as a substrate to give cyclized products by nucleophilic vinyl substitution. And the trends in the syntheses of the heterocyclic compounds was studied and expounded. Besides, the biological activities of the products, especially activity as an agricultural chemical, were examined. Moreover 5-aminomethyl-2-pyrrolidinone was synthesized for the purpose of forming a polynuclear heterocyclic compound containing a similar structure of azasteroid. However only one chlorine of 2,3-dichloro-1,4-naphthoquinone was replaced by an amino group of pyrrolidinone and cyclization did not take place.

Keywords

References

  1. Bull. Chem. Soc. Jpn. v.63 Stereochemistry in Nucleophilic Substitution of Activated Nitro Olefins Park,K.P.;Ha,H.J.
  2. Acc. Chem. Res. v.4 Reactions of Nucleophiles with Ethylenic Substrates Modena,G.
  3. Tetrahedron v.3 Stereoselection in Nucleophilic Sudstitution at an SP² Carbon Miller,I.
  4. Acc. Chem. Res. v.14 Nucleophilic Vinylic Substitution. A Single or a Multi-Step Process? Rappoport,Z.
  5. J. Org. Chem. v.27 Quinolinequinones.Ⅵ. Reactions with Aromatic Amines Pratt,Y.T.
  6. J. Am. Chem. Soc. v.78 Stereospecific Reaction of Nucleophilic Agents with Acetylenes and Vinyl-type Halides.Ⅱ.The Mechanism of the Base-catalyzed Reaction of Vinylidene Chloride with Thiols Truce,W.E.;Boudakian,M.M.
  7. Tetrahedron Letters v.25 Regiochemistry of Nucleophilic Displacements in Chloroquinones Cameron,D.W.;Chalmers,P.J.;Feutrill,G.I.
  8. Bull. Chem. Soc. Jpn. v.44 Reactions of Aliphatic Amines with p-Benzoquinone and Its Chloro Derivatives Yamaoka,T.;Nagakura,S.
  9. Bull. Chem. Soc. Jpn. v.44 Polynuclear Derivatives VanAllan,J.A.;Reynolds,G.A.
  10. J. Org. Chem. v.28 Polynuclear Heterocycles. Ⅵ. The Reaction of 2,3-Dichloro-1,4-naphtoquinone with Aromatic Amines VanAllan,J.A.;Reynolds,G.A.
  11. J. Org. Chem. v.45 Quinone Chemistry. Reaction of 2,3-Dichloro-1,4-napthoquinone with o-Aminophenols under Various Condition Agarwal,N.L.;Schafer,W.
  12. J. Org. Chem. v.45 Syntheses of (S)-5-Substituted 4-Aminopentanoic Acids: A New Class of r-Amino butyric Acid transaminase Inctivators Silverman,R.B.;Levy,M.A.
  13. J. Org. Chem. v.57 Synthesis of (R)-and (S)-4,5-Diaminovaleric Acids Valasinas,A.;Frydman,B.
  14. J. Am. Chem. Soc. v.112 Man-Designed Bleomycin with Altered Sequence Specificity in DNA Cleavage Otsuka,M.;Masuda,T.;Masuda,A.H.;Ohno,M.;Shiraki,T.;Suiura,Y.;Maeda,K.
  15. Tetrahedron Letters v.32 Enantioselective Syntheses of Monomorium Ant Venom Alkaloids: (5R)-2-(5-Hexenyl)-5-nonyl-3,4-di-hydro-2H-pyrrole and (2R,5R)-2-(5-Hexenyl)-5-nonylpyrrolidine from (S)-pyroglutamic acids Rosset,S.;Celerier,J.P.;Lhommet,G.
  16. Tetrahedron Letters v.24 Reduction D'Azides en Primaires par une Methode Generale Utilisant la Reaction de Staudinger Vaultier,M.;Knouzi,N.;Carrie,R.
  17. Comprehensive Organic Synthesis v.6 Trost,B.M.;Fleming,I.