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Quinoline synthesis - Organic chemistry
In addition to the employment of diazonium salts in colour making, these reactive compounds are utilized in many synthetic operations both in the laboratory and in the works. Their appli cation to synthesis depends on the fact that through the diazo reaction the amino-group originally present in an aromatic amine becomes replaceable by other elementary or compound radicals.
The coupling of diazonium salts with active methylene compounds is known as the Japp-Klingemann reaction, a process applicable to nucleoside synthesis. On the other hand, -amination of simple esters is achieved through the hydrogenation of azo or hydrazono esters formed from ketene silyl acetals (eq 9). The reaction with enamines likewise leads to -iminio hydrazones which readily rearrange to heterocycles (eq 10). The nucleophilic addition of also results in cyclization, affording triazoles. In addition, lithium enolates of -substituted ketones, Grignard reagents,, organozinc reagents,, and allylsilanes produce corresponding azo or hydrazono compounds.
Synthesis of amides - Organic chemistry
Catalysis by rhodium phosphine complexes in DMF does not seem very effective.Benzeneselenol is a unique reagent for producing arylhydrazines from diazonium fluoroborates (eq 28); the reaction is applicable to the synthesis of indazolone from -carbamoyl diazonium salts.Diazonium fluoroborates can be used as radical initiators.
AROMATIC DIAZONIUM SALTS In diazotizing aniline and other aromatic amines the base is first converted into its salt, usually the hydrochloride, by the addition of excess of acid (3 molecular proportions of hydro chloric acid). The solution or suspension is cooled and aqueous sodium nitrite is added with stirring, when the nitrous acid liber ated substitutes one nitrogen atom for three hydrogen atoms present in the molecule of the organic salt : It is on account of this replacement of hydrogen by nitrogen, which becomes attached to the nitrogen atom already present in the molecule, that the products now containing a double portion of nitrogen (azote) are termed diazo-compounds. Benzenediazon ium chloride, represented by the above formula, is an extremely soluble salt of explosive character, and for ordinary synthetic and industrial purposes it is not necessary to isolate it. This and other diazonium salts have, however, been prepared in an an hydrous condition by diazotizing the amine salt in alcohol or glacial acetic acid with methyl, ethyl or amyl nitrite, when the diazonium salt is precipitated on the addition of ether (E. Knoevenagel, E. Bamberger, A. Hantzsch).
Volume 94 (2017) Preface Scott E
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