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Catalytic Cyclization of o ‐Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3‐Benzazepines
Author(s) -
ÁlvarezPérez Andrea,
GonzálezRodríguez Carlos,
GarcíaYebra Cristina,
Varela Jesús A.,
Oñate Enrique,
Esteruelas Miguel A.,
Saá Carlos
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505782
Subject(s) - benzazepines , phenethylamines , chemistry , dopaminergic , catalysis , osmium , apomorphine , combinatorial chemistry , stereochemistry , organic chemistry , dopamine , neuroscience , ruthenium , biochemistry , receptor , biology , agonist
Abstract A novel osmium‐catalyzed cyclization of o ‐alkynyl phenethylamines to give 3‐benzazepines is reported. The procedure allows the straightforward preparation of a broad range of dopaminergic 3‐benzazepine derivatives. Mechanistic investigations revealed that the process takes place via osmacyclopropene intermediates, which were isolated and characterized by X‐ray crystallography.