ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Isothiocyanates. VIII. Study of the synthesis of diisothiocyanates and aminoisothiocyanates of acridine

P. Kristián, K. Antoš, A. Hulka, P. Nemec, and Ľ. Drobnica

Slovak Technical University, Bratislava

Abstract: cf. CA 56, 12854e. The problem of the synthesis of 1-isothiocyanato-5-aminoacridine, 2-isothiocyanato-5-aminoacridine, 3-isothiocyanato-5-aminoacridine and 2,8-diisothiocyanatoacridine from the corresponding diaminoacridines is described. Because of the unreactivity of the 5-NH₂ group in 5-aminoacridine it was expected that the other NH₂ group would be converted to isothiocyanate. For 1,5-(I), 2,5-(II) and 3,5-(III) diaminoacridine it was impossible to prep. the corresponding isothiocyanates. In I H bonds are formed between H on the hetero N with N of of the 1-NH₂ group. In II there is a possibility of the formation of a p-quinoid structure from 2-NH2 group with the ionized form of the acridonimine. In III there is a possibility of the formation of an amino-imine tautomeric structure of the 3-NH₂ group. The synthesis of a new compd., 2,8-diisothiocyanatoacridine, m. 200°, by the thiophosgene method is described.

Full paper in Portable Document Format: 1510a730.pdf (in Slovak)

Chemical Papers 15 (10) 730–736 (1961)