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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 2, 1972 - Issue 5
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Original Articles

Synthesis in the Emetine Series XV1) Friedel-Crafts Acylation of N-Acetylhomoveratrylamine: A Facile Synthesis of 9,10-Dimethoxybenzo[a]Quinolizidine

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Pages 315-321 | Received 26 Jun 1972, Published online: 05 Dec 2006

References

  • Brossi , A. , Bruderer , H. , Rachlin , A. I. and Teitel , S. 1967 . Tetrahedron , 24 : 4277 Part XIV:
  • The term benzo[a] quinolizidene for the fully saturated tricyclic system represented by compounds of type 8 is more convenient than the otherwise preferred nomenclature 1,2,3, 6,7, llb-hexahydro-9,10-dimethoxy-4H-benzo[a] quinolizine
  • Brossi , A. , Teitel , S. and Parry , G. V. 1971 . “ Chapter 3 ” . In The Alkaloids , Edited by: Manske , R. H. F. Volume XIII , New York, N.Y. : Academic Press .
  • Pletscher , A. , Brossi , A. and Gey , K. F. 1962 . International Review of Neurobiology , Edited by: Pfeiffer , C. C. and Smythies , J. R. Volume 4 , 275 New York, N.Y. : Academic Press .
  • Beke , D. and Szantay , Cs. 1962 . Chem. Ber. , 95 : 2133
  • Brossi , A. , Bruderer , H. , Da Prada , M. , Steiner , F. A. and Pletscher , A. 1965 . Arnzeim.-Forsch. , 15 : 670
  • Gootjes , J. and Nauta , W. Th. 1965 . Rec. Trav. Chim. Pays-Bas , 84 : 1183
  • Van Dyke , J. W. Jr. , Havera , H. J. , Johnson , R. D. , Vidrio , H. and Viveros , A. 1972 . J. Med. Chem. , 15 : 91
  • Child , R. and Pyman , F. L. 1931 . J. Chem. Soc. , : 36
  • The condensation of 2 with 5-carbomethoxyvaleroyl chloride, followed by the steps outlined above, afforded the 9,10-dinethoxy homolog of 8 containing a seven membered ring. The homologous compound was isolated in the form of the hydrochloride of m. p. 203–206°
  • All melting points (uncorrected) were taken in open capillaries with a Thomas Hoover melting apparatus. Nmr spectra were obtained with a Varian A-60 spectrometer using tetramethylsilane as the internal standard. Reported yields were not optimized and are of isolated products homogeneous to tlc. All compounds gave acceptable elemental analyses. The chloroform and xylene used as solvents were previously dried over Al2O3
  • Fujii , T. 1960 . Chem. Pharm. Bull. , 8 : 266
  • English , J. , Barber , G. W. and Lapides , L. J. 1948 . J. Amer. Chem. Soc. , 70 : 2860

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