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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 iminoacyl-Zr intermediates.

Authors
Type
Published Article
Journal
Chemistry - A European Journal
0947-6539
Publisher
Wiley Blackwell (John Wiley & Sons)
Publication Date
Volume
16
Issue
28
Pages
8419–8426
Identifiers
DOI: 10.1002/chem.201000708
PMID: 20544754
Source
Medline

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 Zr--C bond, and structures of two dihydropyrrolo[3,2-c]azepines were characterized by single-crystal X-ray structural analysis.

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