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Efficient One‐Pot Synthesis of N‐Containing Heterocycles by Multicomponent Coupling of Silicon‐Tethered Diynes, Nitriles, and Isocyanides through Intramolecular Cyclization of IminoacylZr Intermediates
Author(s) -
Zhang Shaoguang,
Zhang WenXiong,
Xi Zhenfeng
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000708
Subject(s) - intramolecular force , silicon , coupling (piping) , chemistry , computational chemistry , photochemistry , combinatorial chemistry , materials science , organic chemistry , metallurgy
Abstract An efficient multicomponent synthesis of 5‐azaindoles and dihydropyrrolo[3,2‐ c ]azepines was achieved by zirconocene‐mediated coupling of silicon‐tethered diynes, nitriles, and isocyanides. The synthesis, structures, and intramolecular cyclization of mono‐ and bis(iminoacyl)Zr intermediates were investigated to elucidate the reaction process. Upon hydrolysis, the isolated mono(iminoacyl)Zr intermediates underwent intramolecular cyclization to afford tetrasubstituted 5‐azaindoles, whereas intramolecular cyclization of bis(iminoacyl)Zr intermediates led to the formation of dihydropyrrolo[3,2‐ c ]azepines. The structure of a bis(iminoacyl)Zr intermediate, formed through insertion of two molecules of CyNC into the ZrC bond, and structures of two dihydropyrrolo[3,2‐ c ]azepines were characterized by single‐crystal X‐ray structural analysis.