Aluminum acetate azide

The properties of chlorine azide resemble those of bromine azide. Pon-sold has taken advantage of the stronger carbon-chlorine bond, i.e., the resistance to elimination, in the chloro azide adducts and thus synthesized several steroidal aziridines. 5a-Chloro-6 -azidocholestan-3 -ol (101) can be converted into 5, 6 -iminocholestan-3l -ol (102) in almost quantitative yield with lithium aluminum hydride. It is noteworthy that this aziridine cannot be synthesized by the more general mesyloxyazide route. Addition of chlorine azide to testosterone followed by acetylation gives both a cis- and a trans-2iddMct from which 4/S-chloro-17/S-hydroxy-5a-azidoandrostan-3-one acetate (104) is obtained by fractional crystallization. In this case, sodium borohydride is used for the stereoselective reduction of the 3-ketone... 

Lithium aluminum hydride reduced )J-azidoethylbenzene to j8-aminoethyl-benzene in 89% yield [600], The azido group was also reduced with aluminum amalgam (yields 71-86%) [149], with titanium trichloride (yields 54-83%) [601], with vanadous chloride (yields 70-95%) [217] Procedure 40, p. 215), with hydrogen sulfide (yield 90%) [247], with sodium hydrosulfite (yield 90%) [259], with hydrogen bromide in acetic acid (yields 84-97%) [232], and with 1,3-propanedithiol (yields 84-100%) [602]. Unsaturated azides were reduced to unsaturated amines with aluminum amalgam [149] and with 1,3-propane-dithiol [602]. 

Aluminum powder, Carbon tetrachloride Aluminum powder, Tetrachlorethylene CNTA, Hydrogen sulfide. Benzene, Lead 11 hydroxide Mercury-ll-nitrate, Sodium azide Mercury, Nitric acid. Alcohol Mercury, Nitric acid. Ethanol Ammonia, Mercury oxide. Nitric acid Nitric acid. Methylene diformamide. Acetic anhydride. Formic acid. Benzene... 

Benzene, Arsenic trichloride, Aluminum chloride. Hexanes Acetic anhydride. Nitric acid, Hexamine, Acetic acid, Methylene chloride. Sodium bicarbonate, Magnesium sulfate, Dioxane, Hydrogen chloride, Acetone, Sodium azide m-phenylenediamine, Methanol, Sodium carbonate, Ethyl chloromate, Ethylene glycol dimethyl ether, Sulfuric acid, Nitric acid... 

Later, it was also claimed that 3-(tetrazolyl)-4//-pyrido[ 1,2-u]pyrimidin-4-ones 159 were obtained in an one-step procedure by heating the appropriate 2-aminopyridine, ethyl (l//-tetrazol-5-yl)acetate, and triethyl orthoformate in dimethylformamide at 90°C for 1 hour, or in boiling tetra-hydrofuran for 6 hours followed by treatment with 1N potassium hydroxide at 50°C for 1 hour, or with anhydrous aluminum chloride under reflux for 6 hours (91EUP462834). 9-Methyl-3-( 1 //-tetrazolyl)-4//-pyrido[ 1,2-a]-pyrimidin-4-one 159 (R = 9-Me) could be prepared when 2-amino-3-meth-ylpyridine hydrochloride and sodium azide were suspended and stirred in dimethylformamide for 1 hour at room temperature, followed by the addition of ethyl ethoxymethylenecyanoacetate, ethoxymethylenemalo-nonitrile, ethyl cyanoacetate and triethyl orthoformate, or malononitrile and triethyl orthoformate and stirring at 90°C for 6-12 hours. Then the reaction mixture was treated with 1 N potassium hydroxide at 50°C for 1 hour, phosphoryl chloride at 90°C for 5 hours, or with concentrated hydrochloric acid at 110°C for 4 hours to give 26-62% yields. 

Silver trifluoroacetate, 327, 328 Silyl ethers, 477-478 Simmons-Smith reagent, 436-437 (3-Sinensal, 283 Sirenin, 424 Sodium, 246, 268, 437 Sodium acetate, 578 Sodium aluminum chloride, 438 Sodium aluminum diethyl dihydride, 438 Sodium aluminum hydride, 316 Sodium amalgam, 41,438-439 Sodium amide, 231, 305,403,439 Sodium amide-Sodium f-butoxide, 439-440 Sodium-Ammonia, 26, 32,134, 260,438 Sodium azide, 9, 77, 210, 323, 440-441 Sodium benzoxide, 111 Sodium bis-(2-methoxyethoxy)aluminum hydride, 164, 293, 360,441-442 Sodium bistrimethylsilylamide, 442-443,... 

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