10531-03-0Relevant academic research and scientific papers
Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-dione from 4,4-disubstituted cyclohexanone enamines and methacryloyl chloride
Ahmed, M. Giasuddin,Ahmed, Syeda Asghari,Akhter, Kawsari,Tsuda, Yoshisuke,Hossain, M. Mahmun,Forsterling, F. Holger
, p. 1273 - 1283 (2007/10/03)
Morpholine enamines 4-acetyl-4-methyl-1-morpholinocyclohexene 4a, 4-acetyl-4-phenyl-1-morpholinocyclohexene 4b, and 4-acetyl-4-isopropenyl-1- morpholinocyclohexene 4c react with methacryloyl chloride to give 1,7-dimethyl-4(N-morpholino) tricyclo[5.3.1.0s
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
, p. 293 - 298 (2007/10/03)
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.
Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones
Giasuddin Ahmed,Iqbal Moeiz, Syed M,Asghari Ahmed,Kiuchi, Fumiyuki,Tsuda, Yoshisuke
, p. 3143 - 3150 (2007/10/03)
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.
Synthesis of Some Substituted Adamantane-2,4-diones from 4,4-disubstituted Cyclohexanone Enamines and α,β-Unsaturated Acid Chlorides
Ahmed, M. Giasuddin,Moeiz, Syed M. Iqbal,Ahmed, S. Asghari,Kiuchi, Fumiyuki,Tsuda, Yoshisuke,Sampson, Paul
, p. 1439 - 1470 (2007/10/03)
Acryloyl and crotonoyl chlorides react with morpholine enamine 4a of 4-acetyl-4-phenylcyclohexanone 3a to give (6R)-6-hydroxy-6-methyl-7-phenyladamantane-2,4-dione 8a and (6R,9R)-6-hydroxy-6,9-dimethyl-7-phenyladamantane-2,4-dione 9a respectively. Cinnamoyl chloride reacts with the same enamine 4a to give two isomers (6R,9R)-6-hydroxy-6-methyl-7,9-diphenyladamantane-2,4-dione 10a and (6S,9R)-6-hydroxy-6-methyl-7,9-diphenyladamantane-2,4-dione 11a which are epimeric at 6-C. Reaction between cinnamoyl chloride and morpholine enamine 4b of 4-acetyl-4-isopropenylcyclohexanone 3b proceeds in a similar manner to produce two isomers, (6R,9R)-6-hydroxy-7-isopropenyl-6-methyl-9-phenyladamantane-2,4-dione 10b and (6S,9R)-6-hydroxy-7-isopropenyl-6-methyl-9-phenyladamantane-2,4-dione 11b also epimeric at 6-C. Acryloyl chloride reacts with morpholine enamine 4c of 4-acetyl-4-methylcyclohexanone 3c to give (6R)-6-hydroxy-6,7-dimethyladamantane-2,4-dione 8c.
Reaction of α,β-Unsaturated Acid Chlorides with 4,4-Disubstituted Cyclohexanone Enamines
Ahmed, M. Giasuddin,Huque, A. K. M. Fazlul,Ahmed, S. Asghari,Mosihuzzaman, Mohammed,Andersson, Rolf
, p. 2815 - 2835 (2007/10/02)
Acrylyl and crotonyl chlorides react with the morpholine enamine of ethyl 1-acetyl-4-oxocyclohexane-1-carboxylate to give ethyl 2-hydroxy-4,6-dioxo-2-methyladamantane-1-carboxylate and ethyl 2-hydroxy-4,6-dioxo-2,10-dimethyladamantane-1-carboxylate respectively.Reaction between crotonyl chloride and morpholine enamine of 4-acetyl-4-methylcyclohexanone proceeds in a similar manner and produces 6-hydroxy-6,7,9-trimethyladamantane-2,4-dione.The corresponding reaction with acrylyl chloride gives a mixture of 6-hydroxy-6,7-dimethyladamantane-2,4-dione and 1-methyl-4-morpholinotricyclo4,9>undecane-2,6-dione, of which the latter was isolated in pure form.The structure of the compounds have been determined by 1H and 13C n. m. r. and mass spectrometry.The course of reactions leading to the formation of different products as well as the stereochemistry of the chiral centres at C-6 and C-9 (or C-2 and C-10) of the adamantane derivatives have been discussed.
