Abstract
N1,N4,3,6-Tetramethyl-N1,N4-diphenyl-1,4-dihydro-1,2,4,5-tetrazine-1,4-dicarboxamide was prepared from 3,6-dimethyl-1,6-dihydro-1,2,4,5-tetrazine, bis(trichloromethyl) carbonate and N-methylaniline. Its structure was confirmed by single-crystal X-ray diffraction. This reaction yields the title compound rather than N1,N2,3,6-tetramethyl-N1,N2-diphenyl-1,2-dihydro-1,2,4,5-tetrazine-1,2- dicarboxamide. The central tetrazine ring of the title compound exhibits a boat conformation and is therefore not homoaromatic.
References
1.
Domingo L.R.
,
Picher M.T.
, and
Saez J.A.
, J. Org. Chem. , 2009 , 74 , 2726 .
2.
Lorincz K.
,
Kotschy A.
,
Tammiku-Taul J.
,
Sikk L.
, and
Burk P.
, J. Org. Chem. , 2010 , 75 , 6196 .
3.
Neunhoeffer H.
, Comprehensive heterocyclic chemistry , 1st edn, ed.
Katritzky A.R.
, Pergamon Press , New York , 1984 , Vol. 3 , pp. 531 .
4.
Sauer J.
, Comprehensive heterocyclic chemistry , 2nd edn, ed.
Boulton A.J.
, Oxford, England : Elsevier , 1996 , Vol. 6 , pp. 901 .
5.
Saracoglu N.
, Tetrahedron , 2007 , 63 , 4199 .
6.
Devaraj N.K.
,
Upadhyay R.
,
Haun J.B.
,
Hilderbrand S.A.
, and
Weissleder R.
, Angew. Chem. Int. Ed. , 2009 , 48 , 7013 .
7.
Han H.S.
,
Devaraj N.K.
,
Lee J.
,
Hilderbrand S.A.
,
Weissleder R.
, and
Bawendi M.G.
, J. Am. Chem. Soc. , 2010 , 132 , 7838 .
8.
Rao G.W.
,
Lu X.J.
, and
Hu W.X.
, J. Chem. Res. , 2010 , 34 , 301 .
9.
Jennison C.P.R.
,
Mackay D.
,
Watson K.N.
, and
Taylor N.J.
, J. Org. Chem. , 1986 , 51 , 3043 .
10.
Rao G.W.
, and
Hu W.X.
, Bioorg. Med. Chem. Lett. , 2006 , 16 , 3702 .
11.
Bemis G.W.
,
Whittle R.R.
, and
Mayo S.L.
, Acta Cryst. , 1984 , C40 , 2076 .
12.
Rao G.W.
, and
Hu W.X.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 3174 .
13.
Hu W.X.
,
Rao G.W.
, and
Sun Y.Q.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 1177 .
14.
Sun Y.Q.
,
Hu W.X.
, and
Yuan Q.
, Synth. Commun. , 2003 , 33 , 2769 .
15.
Skorianetz W.
, and
Kováts E. Sz.
, Helv. Chim. Acta , 1971 , 54 , 1922 .
16.
Skorianetz W.
, and
Kováts E. Sz.
, Helv. Chim. Acta , 1970 , 53 , 251 .
17.
Sheldrick G.M.
, SHELXS-97. Program for the Solution of Crystal Structures. University of Göttingen , Germany , 1997 .
18.
Sheldrick G.M.
, SHELXL-97. Program for the Refinement of Crystal Structures. University of Göttingen , Germany , 1997 .
