Functionalization of a Pyridine Framework through Intramolecular Reissert-Henze Reaction of N-(Carbamoyloxy)pyridinium Salts and Unexpected Insertion of Ethereal Solvents

Autor: Asahara, Haruyasu, Kataoka, Asuka, Hirao, Shotaro, Nishiwaki, Nagatoshi
Jazyk: angličtina
Rok vydání: 2015
Zdroj: European Journal of Organic Chemistry. 2015(18):3994-3999
ISSN: 1099-0690
Popis: A new strategy for synthesis of the 2-pyridyl carbamates is reported. This strategy exploits a new intramolecular transformation of an acyloxy group from N-carbamoyloxypyridinium salts (Reissert-Henze-type reaction) as the key step. Addition of a silver salt effectively accelerates the intramolecular attack of the carbonyl oxygen at the 2-position of the pyridine ring. Additionally, a new rearrangement of the acyloxy group, combined with insertion of an ethereal solvent to give pyridine derivatives having a coordinating tether, is reported.
Databáze: OpenAIRE
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