Expeditious Syntheses of Conjugated Allenyl Esters and Oxazoles through a Cascade Reaction of α-Alkynyl Malonates under Alkaline Conditions

Diethyl α-alkynyl-α-methoxymalonates (2a—e) were smoothly hydrolyzed and then decarboxylated under alkaline conditions employing 1 N KOH in EtOH to give conjugated allenyl esters (6a—e) in high yields, and similar alkaline treatment of diethyl α-alkynyl-α-acetylaminomalonates (5a, b, d, e) furnished...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2006, Vol.54(2), pp.196-203
Hauptverfasser:	Sano, Shigeki, Shimizu, Hisashi, Kim, Kweon, Lee, Woo Song, Shiro, Motoo, Nagao, Yoshimitsu
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkalies Alkynes - chemical synthesis Biomimetics conjugated allenyl ester Cysteine Proteinase Inhibitors - pharmacology decarboxylation Esters - chemical synthesis Hydrolysis Indicators and Reagents Magnetic Resonance Spectroscopy Malonates - chemical synthesis Models, Chemical Models, Molecular Molecular Conformation oxazole Oxazoles - chemical synthesis Spectrometry, Mass, Electrospray Ionization Spectrophotometry, Infrared Stereoisomerism α-alkynyl acetylaminomalonate α-alkynyl methoxymalonate
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Zusammenfassung:	Diethyl α-alkynyl-α-methoxymalonates (2a—e) were smoothly hydrolyzed and then decarboxylated under alkaline conditions employing 1 N KOH in EtOH to give conjugated allenyl esters (6a—e) in high yields, and similar alkaline treatment of diethyl α-alkynyl-α-acetylaminomalonates (5a, b, d, e) furnished unexpectedly the oxazoles (7a, b, d, e) having three substituent groups in excellent yields.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.54.196