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Synthesis of amidocrownophanes with 27‐ and 28‐membered rings and their molecular recognition toward urea and its derivatives
Author(s) -
Hiratani Kazuhisha,
Naher Shamsun,
Karikomi Michinori,
Haga Kazuo
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420416
Subject(s) - chemistry , amide , urea , chloroform , naphthalene , pyridine , aromaticity , tandem , proton nmr , organic chemistry , polymer chemistry , molecule , materials science , composite material
Novel crownophanes with 27‐ and 28‐membered rings having two hydroxyl groups, two amide groups, and aromatic moieties such as naphthalene, pyridine, and phenyl rings were successfully synthesized by a one‐step reaction from the corresponding macrocyclic polyethers via “tandem Claisen rearrengement” in moderate yields. They can solubilize urea and its derivatives into chloroform solution, while the corresponding macrocyclic polyethers do not solubilize them. According to NMR studies, crownophanes 1 and 2 interact with urea and its derivatives forming 1:1 complexes.