Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones

M. Giasuddin Ahmed, Syed M. Iqbal Moeiz, S. Asghari Ahmed, Fumiyuki Kiuchi, Yoshisuke Tsuda

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3143-3150
Number of pages8
JournalTetrahedron
Volume57
Issue number15
DOIs
Publication statusPublished - 2001 Apr 9
Externally publishedYes

Fingerprint

Morpholinos
Adamantane
morpholine

Keywords

  • 4,4-disubstituted cyclohexanone
  • Acryloyl chloride
  • Enamine
  • Morpholine
  • Pyrrolidine
  • Substituted adamantane-2,4-dione
  • Substituted tricyclo [5.3.1.0]undecan-2,6-dione

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Giasuddin Ahmed, M., Iqbal Moeiz, S. M., Asghari Ahmed, S., Kiuchi, F., & Tsuda, Y. (2001). Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones. Tetrahedron, 57(15), 3143-3150. https://doi.org/10.1016/S0040-4020(01)00172-7

Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones. / Giasuddin Ahmed, M.; Iqbal Moeiz, Syed M.; Asghari Ahmed, S.; Kiuchi, Fumiyuki; Tsuda, Yoshisuke.

In: Tetrahedron, Vol. 57, No. 15, 09.04.2001, p. 3143-3150.

Research output: Contribution to journalArticle

Giasuddin Ahmed, M, Iqbal Moeiz, SM, Asghari Ahmed, S, Kiuchi, F & Tsuda, Y 2001, 'Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones', Tetrahedron, vol. 57, no. 15, pp. 3143-3150. https://doi.org/10.1016/S0040-4020(01)00172-7
Giasuddin Ahmed M, Iqbal Moeiz SM, Asghari Ahmed S, Kiuchi F, Tsuda Y. Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones. Tetrahedron. 2001 Apr 9;57(15):3143-3150. https://doi.org/10.1016/S0040-4020(01)00172-7
Giasuddin Ahmed, M. ; Iqbal Moeiz, Syed M. ; Asghari Ahmed, S. ; Kiuchi, Fumiyuki ; Tsuda, Yoshisuke. / Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones. In: Tetrahedron. 2001 ; Vol. 57, No. 15. pp. 3143-3150.
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title = "Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones",
abstract = "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.",
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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

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

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JO - Tetrahedron

JF - Tetrahedron

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