4-Methoxy-l-naphthylamineand 4-methoxy-5,6,7,8-tetrahydro-l-naphthylamine have been used as starting materials to prepare heterocyclic compounds of pharmaceutical interest.Benz(c)acridine benzologs of Atabrine, and 4-diethylaminopropylaminobenzo-(h)quinolines have been prepared from the amines. Lafayette, Ind.
m/z 175 (M+). Phenyl azide,14 p-toluenesulfonyl azide,15 and benzoyl azide,16 were prepared by the methods reported in the literature. 2-Nitroso-2-methylpropane17 and nitrosobenzene18 were also synthesized according to literature methods.ESR Measurements. A solution of 20 mg of azide and 5 mg of 2-nitroso-2-methylpropane (or nitrosobenzene), in 2.0 mL of benzene in an ESR tube, was degassed and then placed in a JEOL JES-PE-3X ESR spectrometer. Strong ESR signals were observed at room temperature.Identification of Gaseous Products by GC-Mass Spectrometry. To a degassed solution of 18 mg of 2-nitroso-2methylpropane in 2.0 mL of benzene was added 18 mg of trifluoromethanesulfonyl azide by a microsyringe, and the solution was allowed to stand for 3 h at room temperature. The gasous product evolved was collected by a microsyringe and analyzed by GC-mass spectrometry using a JEOL JMS-DX 300 mass spectrometer. Two major peaks were observed by GLC (1-m column packed with silicone OV-1 on Chromosorb W); one product with shorter retention time peak (2 min) and m/z 44 (M+) was determined to be nitrous oxide and the other product with longer retention time peak (3 min) and m/z 64 (M+) was determined to be sulfur dioxide.
In this paper, the second of a series, the continuation of a study of certain thio and dithio compounds related to 5,5′‐diacetamido‐8,8′‐diquinolyl disulfide is described. Of the fourteen sulfur compounds synthesized and characterized, which are described in this paper, twelve are new. Several of these have undergone screening tests for antimalarial activity. Incidental to the syntheses reported new methods are described for the preparation of 2,3‐ and 4‐chloro isomers of 5‐nitro‐quinoline.
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