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Isothiocyanates. VI. The synthesis of isothiocyanate derivatives of acridine and benzacridine

P. Kristi√°n

Slovak Technical University, Bratislava

 

Abstract: cf. CA 55, 428i. The synthesis of some new isothiocyanate derivs. of acridine and benzacridine, which may have a specific effect on metabolic and regulation processes of live cells, was described. By the thiophosgene method from the corresponding amines were prepd. 37, 31, and 32.6% 2-, 3- and 4-isothiocyanatoacridines, m. 174°, 167° and 122-3°, resp., and 37.4 and 39% 9-aminobenz[a]acridine and 10-aminobenz[c]acridine, m. 210°, 192°, resp. 1-Isothiocyanatoacridine could not be prepd. because of formation of an H bond of the primary amino group of 1-aminoacridine with a hetero-N of the neighboring ring. The synthesis of 5-isothiocyanatoacridine was not possible due to unreactivity of the acridonimine structure of 5-aminoacridine. For the prepn. of amino-acridones by redn. of nitroacridones, the method of Albert and Ritchie (CA 35, 62596) was applied and found to be the best. An exact method for the sepn. of the mixt. 2-nitro- and 4-nitroacridone was described by improving Goldberg and Kelley's method (CA 40, 34553).

Full paper in Portable Document Format: 155a333.pdf (in Slovak)

 

Chemical Papers 15 (5) 333–345 (1961)

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