Reactions of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)1,2,4-triazines with dienophiles

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Abstract

The reactions of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)-1,2,4-triazines with various dienophiles (2,5-norbornadiene, 1-morpholinocyclopentene, 1,2-dehydrobenzene, and 2-amino-4-phenyloxazole) were studied. It was shown that the presence of a carborane fragment in the 1,2,4-triazine ring causes an atypical reaction with dienophiles without the formation of the expected aza -Diels-Alder reaction products except for the reaction with 2,5-norbornadiene. The reaction of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)-1,2,4triazines with 2-amino-4-phenyloxazole unexpectedly led to the formation of the corresponding 4,5-dihydro1,2,4-triazines. One of the previously described procedures for the direct introduction of a carborane residue into the C5 position of 1,2,4-triazines was optimized.

About the authors

M. I Valieva

Ural Federal University;Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

A. Rammohan

Ural Federal University

E. S Starnovskaya

Ural Federal University;Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

E. A Kudryashova

Ural Federal University

A. P Krinochkin

Ural Federal University;Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

D. S Kopchuk

Ural Federal University;Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

G. V Zyryanov

Ural Federal University;Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: gvzyryanov@gmail.com

O. N Chupakhin

Ural Federal University;Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

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