TY - JOUR
T1 - Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones
AU - Giasuddin Ahmed, M.
AU - Iqbal Moeiz, Syed M.
AU - Asghari Ahmed, S.
AU - Kiuchi, Fumiyuki
AU - Tsuda, Yoshisuke
N1 - Funding Information:
We gratefully acknowledge the services of Dr Abul Hussam of the Department of Chemistry, George Mason University, USA for running the low resolution mass spectra of our samples. We are also grateful to Dr Mahinda Gangoda of the Chemistry Department of the Kent State University, USA who ran NMR spectra of some of our compounds. A fellowship to S. M. I. M by the University Grants Commission of Bangladesh is acknowledged. A research grant to S. A. A by the Islamic Scientific Educational and Cultural Organization (ISESCO) is gratefully acknowledged.
PY - 2001/4/9
Y1 - 2001/4/9
N2 - The morpholine enamines of 4-acetyl-4-phenylcyclohexanone 3a, 4-acetyl-4-isopropenylcyclohexanone 3b, 4-acetyl-4-methylcyclohexanone 3c react with acryloyl chloride to give 1-phenyl-4(N-morpholino)tricyclo[5.3.1.04,9]undecan-2,6-dione 9a, 1-isopropenyl-4(N-morpholino)tricyclo[5.3.1.04,9]undecan-2,6-dione 9b, and 1-methyl-4(N-morpholino)tricyclo[5.3.1.04,9]undecan-2,6-dione 9c, respectively, along with the corresponding substituted adamantane-2,4-diones. The morpholine enamine of 4-acetyl-4-benzylcyclohexa-none 3d and pyrrolidine enamine of 4-acetyl-4-phenylcyclohexanone 3a yield the corresponding 1-benzyl-4(N-morpholino)tricyclo[5.3.1.04,9]undecan-2,6-dione 9d and 8(R)-methyl-1-phenyl-4(N-pyrrolidinyl)tricyclo[5.3.1.04,9] undecan-2,6-dione 9e. No substituted adamantane-2,4-diones were formed in any of the latter two reactions.
AB - The morpholine enamines of 4-acetyl-4-phenylcyclohexanone 3a, 4-acetyl-4-isopropenylcyclohexanone 3b, 4-acetyl-4-methylcyclohexanone 3c react with acryloyl chloride to give 1-phenyl-4(N-morpholino)tricyclo[5.3.1.04,9]undecan-2,6-dione 9a, 1-isopropenyl-4(N-morpholino)tricyclo[5.3.1.04,9]undecan-2,6-dione 9b, and 1-methyl-4(N-morpholino)tricyclo[5.3.1.04,9]undecan-2,6-dione 9c, respectively, along with the corresponding substituted adamantane-2,4-diones. The morpholine enamine of 4-acetyl-4-benzylcyclohexa-none 3d and pyrrolidine enamine of 4-acetyl-4-phenylcyclohexanone 3a yield the corresponding 1-benzyl-4(N-morpholino)tricyclo[5.3.1.04,9]undecan-2,6-dione 9d and 8(R)-methyl-1-phenyl-4(N-pyrrolidinyl)tricyclo[5.3.1.04,9] undecan-2,6-dione 9e. No substituted adamantane-2,4-diones were formed in any of the latter two reactions.
KW - 4,4-disubstituted cyclohexanone
KW - Acryloyl chloride
KW - Enamine
KW - Morpholine
KW - Pyrrolidine
KW - Substituted adamantane-2,4-dione
KW - Substituted tricyclo [5.3.1.0]undecan-2,6-dione
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U2 - 10.1016/S0040-4020(01)00172-7
DO - 10.1016/S0040-4020(01)00172-7
M3 - Article
AN - SCOPUS:0035831964
SN - 0040-4020
VL - 57
SP - 3143
EP - 3150
JO - Tetrahedron
JF - Tetrahedron
IS - 15
ER -