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Parallel Synthesis of Alkyl Tetrazole Derivatives Using Solid Support Chemistry
1Discovery Chemistry Research, Eli Lilly and Company, Indianapolis, Indiana 46285, DePauw University, Greencastle, Indiana, and Parker H. Petit Institute for Bioengineering and Biosciences, Atlanta, Georgia.
Journal of Combinatorial Chemistry
|May 18, 2000
Summary
Researchers developed a method to create diverse omega-chloroalkyl tetrazoles. These compounds were attached to a solid support, enabling the synthesis of various pure alkyl tetrazole derivatives.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- Tetrazoles are important heterocyclic compounds with diverse applications in pharmaceuticals and materials science.
- Solid-phase synthesis offers advantages in efficiency and purification for creating compound libraries.
Purpose of the Study:
- To develop a versatile method for synthesizing omega-chloroalkyl tetrazoles.
- To demonstrate the utility of this method for generating diverse alkyl tetrazole derivatives using solid-phase techniques.
Main Methods:
- Synthesis of omega-chloroalkyl tetrazoles.
- Attachment of tetrazoles to a solid support (resin).
- In situ Finkelstein reaction for nucleophilic alkylation.
- Cleavage of products from the solid support.
Main Results:
- Successful synthesis of several omega-chloroalkyl tetrazoles.
- Demonstration of efficient alkylation of various nucleophiles using the Finkelstein reaction on solid support.
- Generation of pure alkyl tetrazole derivatives after cleavage from the resin.
- Creation of a 5x6 sample library showcasing the method's general applicability.
Conclusions:
- The described sequence provides a robust and versatile approach for the solid-phase synthesis of alkyl tetrazole derivatives.
- This method facilitates the rapid generation of diverse tetrazole libraries for drug discovery and other applications.