Synthesis of 7,12-dihydro-12-phenyl-5H-6,12-methanodibenz[c,f]azocines via N,N-dibenzylphenacylamines

Coskun N., Buyukuysal L.

HETEROCYCLES, cilt.48, sa.1, ss.53-59, 1998 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 48 Sayı: 1
  • Basım Tarihi: 1998
  • Doi Numarası: 10.3987/com-97-7986
  • Dergi Adı: HETEROCYCLES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.53-59
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

N,N-Dibenzylphenacylamines (1) were prepared in high yields by a one-pot reaction and cyclized at room temperature to give 7,12-dihydro-l2-phenyl-5H-6,1 2-methanodibenz[c,f]azocines in high yields. 95% H2SO4 or 70% HClO4 was used as cycIization catalysts. The double-cyclization proceeds smoothly in the cases where electron-donating groups are present in both benzene ring. N-2,3-dimethoxybenzyl-N-benzylphenacylamine (1f) gave the corresponding N-benzyl-1,2-dihydro-4-phenylisoquinoline on treatment with 95% H2SO4 while N-3,4-Dimethoxybenzyl-N-benzylphenacylamine (1a) at the same reaction conditions and reaction time cyclized to the corresponding dibenzazocine. However 1a gave the corresponding dihydroisoquinoline which disproportionates to give N-benzyl-1,2,3,4-tetrahydro-4-phenylisoquinoline and N-benzyl-4-phenylisoquinolinium when treated with 70% perchloric acid al room temperature.