Synthesis of 1-phenyl- and 1-pyridyl-3-pyridoazepines by reductive cyclization of diarylacetonitriles

Several pyrido[2,3- d]azepines and pyrido[3,4- d]azepines, novel aza analogs of the pharmacologically relevant 1-aryl-3-benzazepines, were synthesized by assembling the azepine ring by reductive cyclization of (2-methoxyvinyl)pyridinyl(aryl)acetonitrile derivatives, which were easily derived from co...

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Bibliographic Details
Published in:Tetrahedron 2009-05, Vol.65 (18), p.3653-3658
Main Authors: de la Fuente, M. Carmen, Domínguez, Domingo
Format: Article
Language:English
Subjects:
Aza-1-aryl-3-benzazepines
Chemistry
Diarylacetonitriles
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
Pyrido[2,3- d]azepines
Pyrido[3,4- d]azepines
Reductive cyclization
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Summary:Several pyrido[2,3- d]azepines and pyrido[3,4- d]azepines, novel aza analogs of the pharmacologically relevant 1-aryl-3-benzazepines, were synthesized by assembling the azepine ring by reductive cyclization of (2-methoxyvinyl)pyridinyl(aryl)acetonitrile derivatives, which were easily derived from contiguously substituted bromo(2-methoxyvinyl)pyridines and the corresponding arylacetonitriles. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.02.075