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Synthesis and chemical properties of 8-aryl-7-acyl-1-6-dimethyl-6-hydroxy-4-cyano-5,6,7,8-tetrahydro-3(2H)-isoquinolinones and isoquinolinethiones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

8-Aryl-7-acetyl-1, 6-dimethyl-6-hydroxy-4-cyano-5, 6, 7, 8-tetrahydro-3(2H)-isoquinolinones and -isoquinolinethiones and their sodium salts were obtained by the reaction of cyanoacetamide and cyanothioacetamide with 3-aryl-2, 4-diacetyl-5-methyl-5-hydroxycyclohexanonesinbasicrnedium. 8-Aryl-7-acetyl-6-methoxycarbonyl-1, 6-dimethyl-4-cyano-5, 6, 7, 8-tetrahydro-3(2H)-isoquinolinones were obtained by the reaction of acetyl chloride and the above isoquinolinone sodium salts. The reaction of iodoacetamide and the above isoquinolinethione sodium salts yielded 8-aryl-7-acetyl-3-carbamoylmethylthio-1, 6-dimethyl-4-cyano-5, 6, 7, 8-tetra-hydroisoquinolines, which were cyclized into 1-amino-6-aryl-7-acetyl-2-carbamoyl-5, 8-dimethyl-8-hydroxy-6, 7, 8, 9-tetrahydrothiophene[2,3-c]isoquinolines in basic medium.

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References

  1. T. Kaiho and K. San-nohe, J. Med. Chem.,32, 351 (1989).

    Google Scholar 

  2. E. Knoevenagel and Ruschhaupt, Chem. Ber.,31, 1025 (1898).

    Google Scholar 

  3. J. L. Finar, J. Chem. Soc., No. 1, 674 (1981).

  4. R. Rehberg and F. Krohnke, Liebigs Ann. Chem.,717, 91 (1968).

    Google Scholar 

  5. F. Freeman and D. K. Farguhar, J. Org. Chem.,33, 3648 (1968).

    Google Scholar 

  6. L. M. Jackman and S. Sternhell, Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, Pergamon Press, Oxford-London-Edinburgh-New York-Toronto-Sidney-Paris-Braunschweig (1969).

    Google Scholar 

  7. W. Bremser, B. Franke, and H. Wagner, Chemical Shift Ranges in Carbon-13 NMR Spectroscopy, Verlag Chemie, Weinheim-Deerfield Beach, Florida-Basel (1982).

    Google Scholar 

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Ozols, A.I., Pelcher, Y.Ê., Kalme, Z.A. et al. Synthesis and chemical properties of 8-aryl-7-acyl-1-6-dimethyl-6-hydroxy-4-cyano-5,6,7,8-tetrahydro-3(2H)-isoquinolinones and isoquinolinethiones. Chem Heterocycl Compd 32, 52–58 (1996). https://doi.org/10.1007/BF01169354

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  • DOI: https://doi.org/10.1007/BF01169354

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