Journal
TETRAHEDRON
Volume 67, Issue 29, Pages 5339-5345Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.05.003
Keywords
1,2,4-Triazoles; Aldehydes; Hydrazonoes; Nitrilimine; 1,3-Dipolar cycloaddition
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Funding
- China Medical University [CMU99-COL-11]
- National Science Council of Republic of China [NSC-99-2320-B-039-014-MY3]
- Taiwan Department of Health Clinical Trial and Research Center of Excellence [DOH100-TD-B-111-004]
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A new 'one-flask' synthesis of 3,5-disubstituted 1,2,4-triazoles has successfully been developed to synthesize a series of 3,5-disubstituted 1,2,4-triazoles. The transformation involves the 1,3-dipolar cycloaddition reaction of hydrazonoyl hydrochlorides with oxime intermediates prepared from aldehydes with hydroxylamine hydrochloride in the presence of excess amount of triethylamine. In this 'one-flask' 1,3-dipolar reaction, hydrazonoyl hydrochlorides was concerned as the masked 1,3-dipole nitrilimine under basic condition. Furthermore, this newly developed methodology can be applied to various aldehyde substrates including aliphatic, cyclic aliphatic, aromatic, and heterocyclic aldehydes. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.
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