Benzyne-mediated rearrangement of 3-(2-pyridyl)-1,2,4-triazines into 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles

The reaction between 5-R-6-R1-3-(2-pyridyl)-1,2,4-triazines and benzyne generated in situ in toluene under reflux results in the formation of 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles 3 in up to 60% yields instead of the expected 3-R-4-R1-1-(2-pyridyl)isoquinolines 2. The crystal structure of p...

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Bibliographic Details
Published in:Tetrahedron letters 2013-11, Vol.54 (48), p.6427-6429
Main Authors: Nikonov, Igor L., Kopchuk, Dmitry S., Kovalev, Igor S., Zyryanov, Grigory V., Khasanov, Albert F., Slepukhin, Pavel A., Rusinov, Vladimir L., Chupakhin, Oleg N.
Format: Article
Language:English
Subjects:
1,2,3-Triazoles
1,2,4-Triazines
Arynes
Crystal structure
Formations
Pyrido[1,2-a]indoles
Rearrangement
Tetrahedrons
Toluene
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Summary:The reaction between 5-R-6-R1-3-(2-pyridyl)-1,2,4-triazines and benzyne generated in situ in toluene under reflux results in the formation of 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles 3 in up to 60% yields instead of the expected 3-R-4-R1-1-(2-pyridyl)isoquinolines 2. The crystal structure of product 3c and the proposed mechanism for the formation of 3 are reported.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2013.09.042