Catalytical Rearrangement of 1,6-Dihydro-S-tetrazine with Isocyanate

Abstract

Abstract: 3,6-Dimethyl-1,6-dihydro-S-tetrazine reacts with phenyl isocyanate over different catalysts to afford different products. When using N,N-dimethylaniline as the catalyst, N-phenyl-1,6-dihydro-3,6-dimethyl-S-tetrazine-1-cabonamide was obtained; when using 4-dimethylaminopyridine (DMAP) as the catalyst, the new kind of compound was obtained. Using 14 different substituted phenyl isocyanates, 14 new compounds were prepared with a low or medial yield. The structure of compound 3i was determined by X-ray crystal analysis as N,N′-di(o-methylphenyl)-3,6-dimethyl-1,4-dicarbonamide. It shows that the catalytical rearrangement occurred. The mechanism was discussed briefly with aid of ¹H NMR results. The anticancer activity of these new compounds were tested in vitro. And the results show that some of them have good bioactivity.

Key words: 1,6-Dihydro-S-tetrazine, 1,4-Dihydro-S-tetrazine, Isocyanate, Crystal structure, Rearrangement, Antitumour activity

CLC Number:

O624

TrendMD:

HU Wei-Xiao, SUN Ya-Quan, YUAN Qing, YANG Zhong-Yu. Catalytical Rearrangement of 1,6-Dihydro-S-tetrazine with Isocyanate[J]. Chem. J. Chinese Universities, 2002, 23(10): 1877.

References

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