1-Alkyl-5-((di)alkylamino) Tetrazoles: Building Blocks for Peptide Surrogates

An approach to the synthesis of 1-alkyl-5-((di)alkylamino)tetrazoles by nucleophilic substitution in 1-alkyl-5-sulfonyltetrazoles with anions generated from the primary or secondary amines was developed. Tolerance of the method to the presence of some functional groups (i.e., protected amine) in bot...

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Bibliographic Details
Published in:Journal of organic chemistry 2012-01, Vol.77 (2), p.1174-1180
Main Authors: Tymtsunik, Andriy V, Bilenko, Vitaliy A, Kokhan, Serhiy O, Grygorenko, Oleksandr O, Volochnyuk, Dmitriy M, Komarov, Igor V
Format: Article
Language:English
Subjects:
Amines - chemistry
Chemistry
Chemistry Techniques, Synthetic
Drug Design
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Peptides
Peptides - chemistry
Preparations and properties
Sulfinic Acids - chemistry
Tetrazoles - chemical synthesis
Tetrazoles - chemistry
Urea - chemistry
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Summary:An approach to the synthesis of 1-alkyl-5-((di)alkylamino)tetrazoles by nucleophilic substitution in 1-alkyl-5-sulfonyltetrazoles with anions generated from the primary or secondary amines was developed. Tolerance of the method to the presence of some functional groups (i.e., protected amine) in both components of the reaction was demonstrated. Obtained tetrazoles are promising building blocks for the design of peptide surrogates, in particular, for replacement approaches of alkyl urea derivatives.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2022235