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

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.

Keywords

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