4-(9,10-Dihydroacridin-9-ylidene)thiosemicarbazide and its five-membered thiazole and six-membered thiazine derivatives

Acta Crystallographica. Section C, Crystal Structure Communications
Ivan PotocnákKarel Douglas Klika

Abstract

Two methyl derivatives, five-membered methyl 2-{2-[2-(9,10-dihydroacridin-9-ylidene)-1-methylhydrazinyl]-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene}acetate, C(20)H(16)N(4)O(3)S, (I), and six-membered 2-[2-(9,10-dihydroacridin-9-ylidene)-1-methylhydrazinyl]-4H-1,3-thiazin-4-one, C(18)H(14)N(4)OS, (II), were prepared by the reaction of the N-methyl derivative of 4-(9,10-dihydroacridin-9-ylidene)thiosemicarbazide, C(14)H(12)N(4)S, (III), with dimethyl acetylenedicarboxylate and methyl propiolate, respectively. The crystal structures of (I), (II) and (III) are molecular and can be considered in two parts: (i) the nearly planar acridine moiety and (ii) the singular heterocyclic ring portion [thiazolidine for (I) and thiazine for (II)] including the linking amine and imine N atoms and the methyl C atom, or the full side chain in the case of (III). The structures of (I) and (II) are stabilized by N-H...O hydrogen bonds and different pi-pi interactions between acridine moieties and thiazolidine and thiazine rings, respectively.

References

May 31, 2002·Acta Crystallographica. Section B, Structural Science·Frank H Allen
Apr 5, 2005·Acta Crystallographica. Section C, Crystal Structure Communications·Ján ImrichJuraj Cernák
Dec 14, 2005·Bioorganic Chemistry·Agnieszka J PawłowiczLeif Kronberg
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
May 9, 2008·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jana TomascikováKarel D Klika

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