- Cyclotransformation in the series of fused 5-nitropyridin-2(1H)-ones
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Reactions with excess hydrazine hydrate of 5-nitropyridin-2(1H)-ones fused with benzene, pyridine, and 1,2,3-triazole rings led to a cyclotransformation of the 5-nitro-2-oxopyridine fragment into the 6-methyl-3-oxopyridazine structure. This cyclotransformation is of general character; a probable mechanism of the process is suggested. Details of the assumed mechanism were experimentally confirmed on model compounds.
- Smolyar,Yutilov
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p. 274 - 281
(2008/09/21)
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- Substitution and Ring Closure Reactions of Phthalazine Derivatives
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1-(Phenylthio)- and 1-(hydroxycarbonylmethylthio)-4-methylphthalazines were prepared from 1-chloro-4-methylphthalazines (1).A series of 2-benzyl- and benzenesulfonyl derivatives was prepared from the corresponding halides and 4-methyl-1(2H)-phthalazinone (4). 4-Methyl-1(2H)-phthalazinthione (6) was substituted at SH group to give 1-(benzylthio)- and 1-(ethoxycarbonylmethylthio)-4-methylphthalazines, 7 and 8 respectively.Treatment of hydrazine hydrate with 8 produced 1-hydrazino-4-methylphthalazine (10).However, when the latter compound was treated with 1 it gave 1,2-bis-(4-methylphthalazinyl)hydrazine.Treatment of 10 with aromatic aldehydes in glacial acetic acid gave the corresponding 3-phenyl-s-triazolo-6-methylphthalazines 13. 1-Hydrazino-4-methylphthalazine (10) underwent cyclization reactions with acetic anhydride, ethyl chloroformate, carbon disulphide, ethyl formate, ethyl oxalate and with nitrous acid to give the corresponding triazolo-, triazino- and tetrazolophthalazine compounds.
- Badr, M. Z. A.,El-Sherief, H. A.,El-Naggar, G. M.,Mahgoub, S. A.
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p. 471 - 475
(2007/10/02)
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