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

TETRAHEDRON LETTERS

卷:54

Article

Nikonov, Igor L.¹  Kopchuk, Dmitry S.^1,2  Kovalev, Igor S.¹  Zyryanov, Grigory V.^1,2  Khasanov, Albert F.¹  Slepukhin, Pavel A.²  Rusinov, Vladimir L.^1,2  Chupakhin, Oleg N.^1,2 

[1] Ural Fed Univ, Ekaterinburg 620002, Russia

[2] Postovsky Inst Organ Synth RAS, Ural Branch, Ekaterinburg 620990, Russia

关键词: Arynes;    1,2,4-Triazines;    Rearrangement;    1,2,3-Triazoles;    Pyrido[1,2-a]indoles;   

DOI  :  10.1016/j.tetlet.2013.09.042

来源: Elsevier

【 摘 要 】

The reaction between 5-R-6-R-1-3-(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-R-1-1-(2-pyridyl)isoquinolines 2. The crystal structure of product 3c and the proposed mechanism for the formation of 3 are reported. (C) 2013 Elsevier Ltd. All rights reserved.

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