Synthesis of some substituted adamantane-2,4-diones from 4, 4-disubstituted cyclohexanone enamines and methacryloyl chloride

M. Giasuddin Ahmed, Syeda Asghari Ahmed, Kawsari Akhter, Syed M. Iqbal Moeiz, Yoshisuke Tsuda, Fumiyuki Kiuchi, M. Mahmun Hossain, F. Holger Forsterling

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The reaction of methacryloyl chloride with the morpholine enamine 4a derived from 4-acetyl-4-isopropenylcyclohexanone 3a gave 4,6-anti-6-hydroxy-5,6- dimethyl-7-isopropenyladamantane-2,4-dione 6a and 4,6-syn-6-hydroxy-5,6- dimethyl-7-isopropenyladamantane-2, 4-dione 7a as racemates epimeric at 6-C. Comparable results were found for the corresponding phenyl and benzyl substituted cyclohexanones 3b and 3c. In the case of the methyl-substituted cyclohexanone 3d 4,6- anti-alcohol 7d was isolated in pure form.

Original languageEnglish
Pages (from-to)293-298
Number of pages6
JournalJournal of Chemical Research
Issue number5
DOIs
Publication statusPublished - 2005 May

Keywords

  • Adamantane-2,4-diones 4,4-disubstituted cyclohexanone enamines
  • Methacryloyl chloride

ASJC Scopus subject areas

  • Chemistry(all)

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