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Ar-allyl-3,3-dimethoxy-2-butylamine, 84393-18-0; 3methoxy-3-methyl-2-butanone, 36687-98-6; (2,4-dimethyl-l-penten-3-ylidene)isopropylamine, 87207-90-7. Supplementary Material Available: Physical and spectrometric data of -chloro and -bromo ketimines 1 and 2 (Table I); spectrometric properties of a-cyanoaziridines 3 (Table II); spectrometric data of 1-(JV-alkyl) aminocyclopropanecarbonitriles 4 (Table III); and 13C NMR data of l-(N-alkyl)aminocyclopropanecarbonitriles 4 (Table IV) (9 pages). Ordering information is given on any current masthead page.
A select number of mitomycin C derivatives with a substituted hydrazine group at position 7 were synthesized and tested for antineoplastic activity by using an in vivo test with murine P388 leukemia. Several of the adducts displayed activity comparable to that of mitomycin C. The X-ray-determined crystal structure of one of the derivatives (3f) is reported.
Treatment of 2‐pivaloyl‐1,3‐indandione (1) with hydroxylamine under acidic conditions, results in formation of 8‐t‐butylindeno[1,2‐c]isoxazol‐7‐one (2) while treatment of the triketone with hydroxylamine at neutral or basic pH gave 6 which upon cyclization gave the isomeric 3‐t‐butylindeno[1,2‐c]isoxazol‐4‐one (7). Compound 7 was readily reduced to amine 12 by treatment with hydrazine or hydrogen over platinum. The amine, although quite unreactive, was converted to 3‐t‐butylindeno[1,2‐c]pyrazol‐4‐one (13) with hydrazine or reduced to 15 and 16 with sodium in liquid ammonia and alcohol. Surprisingly, the amine 3 obtained from isoxazole 2 gave reduction product 15 from a sodium‐liquid ammonia reduction and not the expected product 18. Spectral evidence for each of the structures is discussed.
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