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Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1′-diarylbutyl pharmacophore
- Source :
- Organic & Biomolecular Chemistry. 16:4008-4012
- Publication Year :
- 2018
- Publisher :
- Royal Society of Chemistry (RSC), 2018.
-
Abstract
- 1,1'-Diarylbutyl groups are a common pharmacophore found in many biologically active small molecules. To access these systems under mild conditions, the reaction of diarylmethyl trichloroacetimidates with allyltributylstannanes was explored. Simply heating allyltributylstannane with the trichloroacetimidate resulted in substitution of the imidate with an allyl group. Unlike other methods used to access these systems, no strong base, transition metal catalyst, Brønsted acid or Lewis acid promoter was required to affect the transformation. Conversions are best with electron rich benzylic trichloroacetimidate systems, where excellent yields are achieved just by refluxing the reactants together in nitromethane.
- Subjects :
- Hot Temperature
Nitromethane
010405 organic chemistry
Organic Chemistry
Tin Compounds
Biological activity
Chemistry Techniques, Synthetic
010402 general chemistry
01 natural sciences
Biochemistry
Combinatorial chemistry
Small molecule
Article
0104 chemical sciences
Catalysis
chemistry.chemical_compound
chemistry
Transition metal
Drug Design
Acetamides
Chloroacetates
Lewis acids and bases
Physical and Theoretical Chemistry
Pharmacophore
Brønsted–Lowry acid–base theory
Subjects
Details
- ISSN :
- 14770539 and 14770520
- Volume :
- 16
- Database :
- OpenAIRE
- Journal :
- Organic & Biomolecular Chemistry
- Accession number :
- edsair.doi.dedup.....41c87497ba7e1eea08af6bf1e60391b9