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A study about the synthesis of seven-membered-ring analogues of ketamine

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Abstract

Synthesis of seven-membered ring analogues of ketamine was studied with two strategies. In the first approach a sequence of five reactions was used which previously applied for ketamine synthesis. This strategy led to formation of 1-[(2-chlorophenyl)(methylimino)methyl]cyclohexan-1-ol as a precursor for the target molecule. In the second approach, we have designed and attempted to synthesize a new analogue of ketamine applying challenging reactions such as ring expansion and selective bromination. The result of this route is synthesis of some interesting compounds such as 6-phenyl-1-oxa-4-thiaspiro[4.6]undecane, 3-bromo-6-phenyl-1-oxa-4-thiaspiro[4.6]undecane and 2,7-dibromo-2-phenylcycloheptanone.

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Acknowledgments

We gratefully acknowledge financial support from the Research Council of Imam Hossein University.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Imam Hossein University, Tehran, Iran

    Abolghasem Moghimi, Mohammad Reza Shahdadi & Morteza Sadeghzadeh

  2. Department of Nanochemistry, Nanotechnology Center, Urmia University, G. C., P. O. Box 165-5715944931, Urmia, Iran

    Sajjad Keshipour

Authors
  1. Abolghasem Moghimi
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  2. Mohammad Reza Shahdadi
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  3. Sajjad Keshipour
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  4. Morteza Sadeghzadeh
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Correspondence to Abolghasem Moghimi.

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Moghimi, A., Shahdadi, M.R., Keshipour, S. et al. A study about the synthesis of seven-membered-ring analogues of ketamine. Res Chem Intermed 41, 6957–6966 (2015). https://doi.org/10.1007/s11164-014-1790-7

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