Acetamide bromo-, derivatives

Nitration of pyrido[l,2-f>]cinnolin-6-ium hydroxide inner salt 17 (R = H) and its 2-acetamide derivative afforded its 2-nitro and 2-acetamido-3-nitro derivatives, respectively. The reaction of 17 (R = H) with iodine monochloride afforded the 2-iodo derivative. The 2-cyano derivative was obtained from the 2-bromo derivative of 17 (R = H) with Cu(I)CN. Treatment of 17 (R = H) with P4S10 afforded the 11-mercapto derivative 41 (74JHC125). 

It is prepared by brominating adamantane and treating the resulting bromo derivative with acetonitrile in the presence of sulphuric acid to obtain N-(l-adamantanyl) acetamide. This on alkaline hydrolysis and treatment with hydrochloric acid affords the official compoimd. 

The earliest examples of such fluorine-18 labelling are 2- and 6-[ F]fluoronico-tinic acid diethylamide and 2- and 6-[ F]fluoronicotine (Fig. 5). All were obtained in up to 40-50% radiochemical yield from the corresponding 2- and 6-chloro-(or bromo-) pyridine derivatives and [ F]fluoride as its cesium salt, in melted acetamide or DMSO at about 200 °C for 30 min [226-229]. 

Usually, the cone isomer is formed in the presence of Na cations. Na2C03 in acetone or acetonitrile is often used for reactive alkylating agents such as bromo- or chloroac-etates, -acetamides or -ketones (XCH2COR, X = Cl, Br), while NaH in DMF or THF/DMF (sometimes MeCN) is the standard for alkyl bromides, iodides or tosylates Derivatives with four bulky residues such as Y = P(C6H5)2 or Y = CH(C02Et)2 have been obtained in the cone conformation. 

Polyamine chain extension, 48-56 by acrylamide 51, 52. 53 by aziridine 48,49 by l-bromo-3-chloropropane, 55 by (2-bromoethyl)phthalimide, 51 by 3-bromopropylphthalimide, 53 by chloroacetonitrilc, 51 by chloroacetyl chloride. 50 by lV-(2-chloroethyl)acetamide, 52 by derivatives of chloroacetic acid. 50 by dichloro(o)-bromoalkyl)boranes. 56 by IV-ethylchloroacetamide, 52 by 3-phthalimidopropyl tosylate, 54 by /V-tosyl-2-bromoethylamine, 49 by 2-(N-tosylamino)ethyl tosylate. 49 by Af-tosylaminoacetyl chloride, 50 Polyamino diols. 59 Polyaza-crown macrocycles. 349-367 alkyl-substituted. 364.365 from bis-sulfonamides, 358-361 from diacid dichlorides, 352-357 from diesters, 352-357 from dihalides, 362-366 from diols, 366 from ditosylates. 362-366 Polyaza-crown macrocycles (miscellaneous), table. 392... 

Acetanilide (i.e., the acetyl derivative of aniline) on being subjected to bromination (with Bvg) in a medium of glacial acetic acid gives rise to the /jura-bromoacetanilide with the liberation of a mole of HBr. The acetamide (—NHCOCHg) is an ortho, para director function hence, the incoming bromo moiety shall yield both ortho- and para-isomers. The latter is produced predominantly (upto 90%) as a white solid. 

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