Literature DB >> 16462063

Expeditious syntheses of conjugated allenyl esters and oxazoles through a cascade reaction of alpha-alkynyl malonates under alkaline conditions.

Shigeki Sano1, Hisashi Shimizu, Kweon Kim, Woo Song Lee, Motoo Shiro, Yoshimitsu Nagao.   

Abstract

Diethyl alpha-alkynyl-alpha-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 alpha-alkynyl-alpha-acetylaminomalonates (5a, b, d, e) furnished unexpectedly the oxazoles (7a, b, d, e) having three substituent groups in excellent yields.

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Year:  2006        PMID: 16462063     DOI: 10.1248/cpb.54.196

Source DB:  PubMed          Journal:  Chem Pharm Bull (Tokyo)        ISSN: 0009-2363            Impact factor:   1.645


  1 in total

1.  Possible involvement of radical intermediates in the inhibition of cysteine proteases by allenyl esters and amides.

Authors:  Yoshio Takeuchi; Tomoya Fujiwara; Yoshihito Shimone; Hideki Miyataka; Toshio Satoh; Kenneth L Kirk; Hitoshi Hori
Journal:  Bioorg Med Chem Lett       Date:  2008-10-05       Impact factor: 2.823

  1 in total

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