Michael 1:1 adducts by acid catalyzed reaction during synthesis of spiro and spiroketal compounds

Authors

  • MM Hossain Department of Chemistry, University of Dhaka, Dhaka-1000, Bangladesh
  • ME Halim Department of Chemistry, University of Dhaka, Dhaka-1000, Bangladesh
  • MM Islam Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka-1205, Bangladesh
  • K Akhter Department of Chemistry, University of Dhaka, Dhaka-1000, Bangladesh
  • SM Ahmed Department of Chemistry, American International University-Bangladesh, 408/1 (Old Ka-66/1) Kuratoli Road, Kuril, Khilkhet, Dhaka-1229, Bangladesh
  • UKR Romman Department of Chemistry, University of Dhaka, Dhaka-1000, Bangladesh
  • MG Ahmed Department of Chemistry, University of Dhaka, Dhaka-1000, Bangladesh

DOI:

https://doi.org/10.3329/bjsir.v55i4.50967

Keywords:

Michael addition; 1,3-cyclohexanedione; Dimedone; Diarylideneacetone

Abstract

Four Michael 1:1 adducts 2-[1,5-bis-(2-methoxyphenyl)-3-oxo-pent-4-enyl]-cyclohexane-1,3- dione 3a, 2-[1,5-bis-(2-methylphenyl)-3-oxo-pent-4-enyl]-cyclohexane-1,3-dione 3b, 2-[1,5-bis- (2-chlorophenyl)-3-oxo-pent-4-enyl]-cyclohexane-1, 3-dione 3c and 2-[1,5-Bis-(2-chloro- phenyl)- 3-oxo-pent-4-enyl]-5,5-dimethyl-cyclohexane-1,3-dione 3d have been synthesised by the application of Michael reaction between 1, 3-cyclohexanedione 1a or dimedone (5, 5-dimethylcy clohexane-1, 3-dione) 1b and trans,trans diarylideneacetone [1,5-diaryl-1,4-pentadien-3-one] 2a-c using acid catalyst. These adducts may be regarded as the intermediate of spiro [5.5] undecane compounds which can be achieved effectively via intramolecular cyclization of the Michael 1:1 adduct. The structures of the Michael 1:1 adducts 3a-d were determined by their UV, IR, 1H-NMR, 13C-NMR, DEPT-135 spectral data, HRMS and elemental analyses.

Bangladesh J. Sci. Ind. Res.55(4), 283-288, 2020

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Published

2020-12-27

How to Cite

Hossain, M., Halim, M., Islam, M., Akhter, K., Ahmed, S., Romman, U., & Ahmed, M. (2020). Michael 1:1 adducts by acid catalyzed reaction during synthesis of spiro and spiroketal compounds. Bangladesh Journal of Scientific and Industrial Research, 55(4), 283–288. https://doi.org/10.3329/bjsir.v55i4.50967

Issue

Vol. 55 No. 4 (2020)

Section

Articles

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