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Synthesis of new arylbenzofurodiazepin‐6‐ones
Author(s) -
Viti Giovanni,
Giannotti Danilo,
Nannicini Rossano,
Ricci Renzo,
Pestellini Vittorio
Publication year - 1990
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.5570270535
Subject(s) - diazepine , chemistry , benzofuran , ring (chemistry) , nucleophile , amine gas treating , stereochemistry , molecule , medicinal chemistry , organic chemistry , catalysis
Two new tetracyclic structures, containing the diazepine ring, were synthesized: 5,6‐dihydro‐12 H ‐benzofuro[3,2‐ b ][1,5]benzodiazepin‐6‐one and 5,6‐dihydro‐12 H ‐benzofuro[3,2‐ b ]pyrido[3,2‐ f ][1,5]diazepin‐6‐one. Thus N ‐(2‐haloaryl)‐2‐[(2‐cyanophenyl)oxy]acetamides were cyclized to the corresponding N ‐(2‐haloaryl)‐3‐amino‐2‐benzofurancarboxamides and then, through the formation of the central diazepine ring, to the title compounds. Formation of the diazepine ring took place only when an electron‐withdrawing group was present in the molecule to facilitate the nucleophilic attack of an amine in the benzofuran intermediate.