Electrophilic Reactions of 7-(Trifluoromethyl)-2,3-dihydro- 1H-pyrrolizine: a Way Towards New Building Blocks

Anton A. Klipkov; Igor I. Gerus

doi:10.24959/ophcj.23.284640

Authors

Anton A. Klipkov V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine; National University of Kyiv-Mohyla Academy, Ukraine https://orcid.org/0000-0002-2553-8232
Igor I. Gerus V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine, Ukraine https://orcid.org/0000-0001-5086-9466

DOI:

https://doi.org/10.24959/ophcj.23.284640

Keywords:

electrophilic reactions, halogenation, acylation, trifluoromethyl, heterocycles, organic synthesis

Abstract

Aim. To synthesize new fluoro-containing building blocks for medicinal chemistry purposes using electrophilic reactions of 7-(trifluoromethyl)-2,3-dihydro-1H-pyrrolizine.
Results and discussion. Synthetic approaches to 5-halogeno- and 5-acyl-7-(trifluoromethyl)-2,3-dihydro-1H-pyrrolizines have been developed. The obtained new trifluoromethyl-containing pyrrolyzines are promising building blocks for medicinal chemistry.
Experimental part. The synthesis of the target compounds began with known 7-(trifluoromethyl)-2,3-dihydro-1H-pyrrolizine and included halogenation and acylation reactions using N-halogen succinimides and acylating reagents.
Conclusions. New synthetic approaches to a number of 7-(trifluoromethyl)-2,3-dihydro-1H-pyrrolizines with various substituents, such as halogen atoms or acyl groups, at the position 5 of the pyrrole ring have been developed. This opens the door to the use of such promising trifluoromethyl-containing building blocks for medicinal chemistry needs.

Supporting Agency

The work was supported by the National Academy of Sciences of Ukraine (grant No. 0122U000443).

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References

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