Premium
Research on nitrogen heterocyclic compounds. XII. Synthesis of 5 H ‐pyrrolo[1,2‐ b ][2]benzazepine derivatives
Author(s) -
Stefancich Giorgio,
Artico Marino,
Massa Silvio,
Vomero Salvatore
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160731
Subject(s) - benzazepine , chemistry , pyrrole , benzazepines , ring (chemistry) , stereochemistry , phosphoric acid , medicinal chemistry , potassium , organic chemistry
Several routes to the synthesis of the unknown 5 H ‐pyrrolo[1,2‐ b ][2]benzazepine ring system have been explored. 1‐(2‐Cyanobenzyl)pyrrole was useful as starting material to obtain 1‐(2‐earboxymelhylbenzyl)pyrrole and 1‐(2‐chloromethylbenzyl)‐2‐pyrrolecarboxaldehyde. Poly‐phosphoric acid catalyzed intramolecular cyclization of the former substance and treatment of the latter compound with potassium cyanide led to 11‐oxo‐10,11‐dihydro‐5H‐pyrrolo[1,2‐ b ]‐[2]benzazepine and to 10‐cyano‐5 H ‐pyrrolo[1,2‐ b ][2]benzazepine, respectively. Starting from these materials the synthesis of the parent nucleus 5 H ‐pyrrole[1,2‐ b ][2]benzazepine and its 10,11‐dihydro‐ and 1,2,3,10,11,11a‐hexahydroderivatives has been realized.