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Abstract 3_Aryl-3-chlaropyricazines (53a-c) were prepared from the reaction cr c_dryi_2>3-c±Lhydrapyridazin-3-Qnes (52a-c) with phosphorus oxyChlo— ride. 6-Aryl-2,3-ctLhydro-4-fnethyl-pyridazin-3-ones (56a-c) were prepared r’rom the reaction of 6—aryI.^-2.,3,4, 5-tetrahyDROPyridazin—3—ones (54a—c) *itn formaldehyde in alcoholic potassium hydroxide. 5-Aryl-3-chlara-4-rnethylpyridazines (57a—c) were similarly prepared by the action of phosphorus oxychloride on 6—aryl-2,3-dihydro-4-methyl-pyridazin-3—ones (56a-c), the infrared and ultraviolet spectra of the i-chloropyridazines obtained were discussed. 3-Chloropyridazines (53a & b) and (57a) reacted with sodium azide in n-butanol to give 6—aryl—tetrazolo ( 1, S-b ] pyridazines (60a & b) and c—(j,4—damethylphenylj-S-nnethyl-tetrazala [ 1, 5-b ]pyridazine (60c). The sane products (SOa-c) were prepared from the reaction of 3—chloropyrida— zines (53a & b) and (57a) with hydrazine hydrate, followed by nitrosa-tion of the unstable hydrazinopyridazines obtained (64a-c) to give the cyclic tetrazoles (60a-c). When 6-aryl-3-chloropyridazines (53a & b) and 3—chlora—6-(3,4—di— methylphenyl)-4-methylpyridazines (57a) reacted with sodium methoxi.de, tney gave 3-fnethoxypyridazines (65a-c). |