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Functionalization of a Pyridine Framework through Intramolecular Reissert–Henze Reaction of N ‐(Carbamoyloxy)pyridinium Salts and Unexpected Insertion of Ethereal Solvents
Author(s) -
Asahara Haruyasu,
Kataoka Asuka,
Hirao Shotaro,
Nishiwaki Nagatoshi
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500443
Subject(s) - chemistry , pyridinium , pyridine , intramolecular force , salt (chemistry) , protecting group , surface modification , ring (chemistry) , medicinal chemistry , solvent , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
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.