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Paper | Regular issue | Vol 60, No. 4, 2003, pp.899-908
Published online, 3rd March, 2003
DOI: 10.3987/COM-03-9740
A New Method for Synthesis of Crown Ether Type Pyridinophanes

Masayuki Sato,* Tsunehisa Oda, Ken-ichi Iwamoto, and Satoshi Fujii

*Schol of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan

Abstract

Bis(acylketene) (3) thermally generated from Meldrum’s acid derivative (2) underwent intramolecular [4+2] cycloaddition to produce bridged dehydroacetic acid derivative (4). Heating 4 with methylamine and ammonia afforded crown ether type pyridinophanes (5) and (6) (12-crown-4), respectively. Reaction of the ketene (3) with (ethylene glycol)s afforded macrolactones (11-13) in satisfactory yields. Molecular structures of 4 and 6 are discussed based on X-Ray crystallographic analysis.