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
Publication statusPublished - 2005 May
Externally publishedYes

Fingerprint

Cyclohexanones
Adamantane
Alcohols
cyclohexanone
morpholine
methacryloyl chloride

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Ahmed, M. G., Ahmed, S. A., Akhter, K., Iqbal Moeiz, S. M., Tsuda, Y., Kiuchi, F., ... Forsterling, F. H. (2005). Synthesis of some substituted adamantane-2,4-diones from 4, 4-disubstituted cyclohexanone enamines and methacryloyl chloride. Journal of Chemical Research, (5), 293-298.

Synthesis of some substituted adamantane-2,4-diones from 4, 4-disubstituted cyclohexanone enamines and methacryloyl chloride. / Ahmed, M. Giasuddin; Ahmed, Syeda Asghari; Akhter, Kawsari; Iqbal Moeiz, Syed M.; Tsuda, Yoshisuke; Kiuchi, Fumiyuki; Hossain, M. Mahmun; Forsterling, F. Holger.

In: Journal of Chemical Research, No. 5, 05.2005, p. 293-298.

Research output: Contribution to journalArticle

Ahmed, MG, Ahmed, SA, Akhter, K, Iqbal Moeiz, SM, Tsuda, Y, Kiuchi, F, Hossain, MM & Forsterling, FH 2005, 'Synthesis of some substituted adamantane-2,4-diones from 4, 4-disubstituted cyclohexanone enamines and methacryloyl chloride', Journal of Chemical Research, no. 5, pp. 293-298.
Ahmed, M. Giasuddin ; Ahmed, Syeda Asghari ; Akhter, Kawsari ; Iqbal Moeiz, Syed M. ; Tsuda, Yoshisuke ; Kiuchi, Fumiyuki ; Hossain, M. Mahmun ; Forsterling, F. Holger. / Synthesis of some substituted adamantane-2,4-diones from 4, 4-disubstituted cyclohexanone enamines and methacryloyl chloride. In: Journal of Chemical Research. 2005 ; No. 5. pp. 293-298.
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AU - Ahmed, Syeda Asghari

AU - Akhter, Kawsari

AU - Iqbal Moeiz, Syed M.

AU - Tsuda, Yoshisuke

AU - Kiuchi, Fumiyuki

AU - Hossain, M. Mahmun

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AB - 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.

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