Versatile Access to C-4-Substituted 2-Amino-1,3-azoles from Hydropyridines in Oxidative Conditions

Various substituted 2-aminotetrahydroazolopyridines and 2-aminohexahydroazolopyridines have been prepared by bromine-mediated addition of protected guanidine or urea to hydropyridine derivatives. The pH-dependent regioselective cleavage of the resulting aminal function led to the 2-aminoazole produc...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-09, Vol.70 (20), p.8208-8211
Main Authors: del Rayo Sanchez Salvatori, Maria, Abou-Jneid, Robert, Ghoulami, Saïd, Martin, Marie-Thérèse, Zaparucha, Anne, Al-Mourabit, Ali
Format: Article
Language:English
Subjects:
Amines - chemistry
Azoles - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Kinetics
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Organic chemistry
Oxidation-Reduction
Preparations and properties
Pyridines - chemistry
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Summary:Various substituted 2-aminotetrahydroazolopyridines and 2-aminohexahydroazolopyridines have been prepared by bromine-mediated addition of protected guanidine or urea to hydropyridine derivatives. The pH-dependent regioselective cleavage of the resulting aminal function led to the 2-aminoazole products III. The yields of the bicycles of type II, and their conversion into azoles III depends on the electronic properties of the substituents on the nitrogen of the tetrahydopyridine.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050862o