TY - JOUR
T1 - Synthesis of some substituted adamantane-2,4-diones from 4, 4-disubstituted cyclohexanone enamines and methacryloyl chloride
AU - Ahmed, M. Giasuddin
AU - Ahmed, Syeda Asghari
AU - Akhter, Kawsari
AU - Iqbal Moeiz, Syed M.
AU - Tsuda, Yoshisuke
AU - Kiuchi, Fumiyuki
AU - Hossain, M. Mahmun
AU - Forsterling, F. Holger
PY - 2005/5
Y1 - 2005/5
N2 - 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.
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.
KW - Adamantane-2,4-diones 4,4-disubstituted cyclohexanone enamines
KW - Methacryloyl chloride
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U2 - 10.3184/0308234054323904
DO - 10.3184/0308234054323904
M3 - Article
AN - SCOPUS:21344451888
SN - 0308-2342
SP - 293
EP - 298
JO - Journal of Chemical Research
JF - Journal of Chemical Research
IS - 5
ER -