Abstract
Two new single-step reactions allowing the construction of two heterocyclic motifs are reported. Both processes involve 5-substituted 1,3,4-thiadiazol-2- amines as starting materials. Reaction with 1-fluoro-2-nitrobenzenes in presence of Hünig's base permitted the convenient synthesis of various 3-substituted 1-aryl-5-amino-1,2,4-triazoles. Reaction with 2-chloro-3- nitropyridines and 2-chloro-5-nitropyridines in similar conditions readily gave access to a number of [1,2,4]triazolo[1,5-a]pyridines. In absence of base, adducts composed by one aromatic unit and two thiadiazole units were formed. This observation and previous work by Anders and co-workers led to the suggestion of plausible mechanisms for these reactions.
Original language | English |
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Pages (from-to) | 1669-1680 |
Number of pages | 12 |
Journal | Tetrahedron |
Volume | 69 |
Issue number | 5 |
DOIs | |
Publication status | Published - 4 Feb 2013 |
Keywords
- Aminotriazole
- Condensation
- Dimroth rearrangement
- Ring formation
- Single-step synthesis
- Triazolopyridine
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Dive into the research topics of 'Direct access to 1-aryl-5-amino-1,2,4-triazoles and [1,2,4]triazolo[1,5-a] pyridines by two new single-step reactions from 1,3,4-thiadiazol-2-amines'. Together they form a unique fingerprint.Equipment
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Physical Chemistry and characterization(PC2)
Johan Wouters (Manager) & Carmela Aprile (Manager)
Technological Platform Physical Chemistry and characterizationFacility/equipment: Technological Platform
Datasets
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CCDC 894884: Experimental Crystal Structure Determination
Loones, K. T. J. (Contributor), Mammoliti, O. (Contributor), Nguyen, A. T. (Contributor), Quinton, E. M. (Contributor), Van Lommen, G. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013
DOI: 10.5517/ccz167f, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccz167f&sid=DataCite
Dataset
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CCDC 894882: Experimental Crystal Structure Determination
Loones, K. T. J. (Contributor), Mammoliti, O. (Contributor), Nguyen, A. T. (Contributor), Quinton, E. M. (Contributor), Van Lommen, G. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013
DOI: 10.5517/ccz165c, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccz165c&sid=DataCite
Dataset
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CCDC 894883: Experimental Crystal Structure Determination
Loones, K. T. J. (Contributor), Mammoliti, O. (Contributor), Nguyen, A. T. (Contributor), Quinton, E. M. (Contributor), Van Lommen, G. (Contributor) & Wouters, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013
DOI: 10.5517/ccz166d, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccz166d&sid=DataCite
Dataset