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and M.Yu. Antipin, Heteroatom Chem., 2004, 15, 199; (b) T. S. Novikova,
T. M. Mel’nikova, O.V. Kharitonova,V. O. Kulagina, N. S.Aleksandrova,
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C(8)
C(3)
N(8)
N(7)
N(1)
C(7)
C(5)
N(3)
N(4)
Figure 1 ORTEP view (thermal ellipsoids are shown with 50% probability)
of the molecule of 6c.
The pyrazole and the tetrazine rings are practically coplanar
that imply conjugation between them. This is supported by the
length [1.393(2) Å] of N(2)–C(6) bond which is shorter than
the standard X-ray value (1.431 Å).14 Coplanarity of these rings
leads to short [2.849(2) Å] intramolecular contact between N(6)
and C(4) atoms. The N(7)–H(7) fragment is in the plane of the
tetrazine ring while 1,2,4-triazole ring is oriented nearly perpen-
dicular to the conjugated part of the molecule of 6c, what can be
explained by sterical hindrance.
In conclusion, we have developed a very mild, efficient and
scalable protocol for the synthesis of secondary polynitrogen
dihetarylamines using an inexpensive commercially available
reagent. Future work will look at extending the conditions
employed in this study to the construction of other tetrazine
derivatives.
A part of this work was supported by the Russian Foundation
for Basic Research (grant nos. 12-03-31346 and 12-03-12012)
and the Ministry of Education and Science of the Russian Federation
(The Federal Target Program ‘Research and Educational Staff of
Innovative Russia in 2012–2013’, grant no. 14.B37.21.0827).
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1999, 35, 1392 (Russ. J. Org. Chem., 1999, 35, 1363); (d) G. L. Rusinov,
Online Supplementary Materials
Supplementary data associated with this article can be found
in the online version at doi:10.1016/j.mencom.2012.11.007.
I. N. Ganebnykh and O. N. Chupakhin, Zh. Org. Khim., 1999,
35, 1379
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Received: 1st June 2012; Com. 12/3936
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