Thiosemicarbazciiies of 41 formyl heterocycles and two heterocyclic ketones were prepared and tested on four mouse tumor systems. The variables studied included: 16 ring systems, different positions of attachment of the formyl group relative to the ring heteroatoms, additional ring substituents, and terminal substituents in the thiosemicarbazone side chain. The minimum requirement for act,ivity is formyl group attachment to a ring carbon CY to an uneiicumbered ring nitrogen of heteroaromatic character. The T-electron density milst be low at this ring carbon and fairly high at the ring nitrogen. All the active compounds are potent ligands for the transition metals from iron through zinc. The aiititiimor activities of the thiosemicarbaaones of 1-formylisoquirioline and 3-hydroxy-2-formylpyridine are siifficiently good to merit extensive further study.

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MethylglyoxalBi.s-(gcanylhydrazoxes) 283 2-Methylthio-2-imidazoline Hydrochloride.-A mixture of 209.5 g. (2.05 moles) of ethylenethiourea, 120 ml. (2.36 moles) of methyl chloride, and 250 ml. of methanol was heated in a stainless steel bomb at 100°for 3 hr. The reaction mixture was filtered to obtain 196 g. of material melting at 166-169°. The filtrate was diluted with ether to obtain an additional 92.5 g. of product, m.p. 161-166°. Total yield was 288.5 g. (92%).

Brfiltered. The solids were extd with dil HC1, and the ext was brought to pH 7 with NaOH, whereupon a ppt formed. This ppt of 3d (153 mg, 16%) was washed with H20 and dried in air. It has an ir spectrum superimposable with that of the same product prepd from 3b.2-Methylamino-6I7-pyrrolo[3,2-e]benzothiazole (3c) was prepd as described for 3d from 3b. From 454 mg of 3a was obtd, after recrystn from MeOH, 158 mg (53%) of 3c of yellow cryst, mp 195-196°. Anal. (C10II9N3S) C, , N, S. 5,6,7,8-Tetrahydropyrrolo[4,3,2-de]cinnolin-3-2jfI-one (7).-A mixt of 890 mg of 4-oxo-4,5,6,7-tetrahydroindole-3-carboxamide (5)4 1and 7 ml of hydrazine hydrate heated at reflux temp for 2 hr, cooled, and filtered. Recrystn of the product from MeOH gave 431 mg (65%) of 7 as white solid which did not melt at < 350°; uv max 233 (e 10,000), 267 (5700), 276 (6100), 298 (4700); ir 3.1-3.45 µ (NH), 6.15 (CONH); nmr (CF3C02H) 11.6 (broad, pyrrole NH), 7.98 (d, J = 2.5 Hz, pyrrole, deshielded by CO), 2.7-2.4 (m, 6, CH2CH2CH2) ppm.