Synthesis from hydrogen cyanide derivatives

Synthesis of Heterocycles from Hydrogen Cyanide Derivatives D. S. Donald and O. W. Webster... 

Synthesis of imidazoles from hydrogen cyanide derivatives 87-AHC(41)1. 

Homolytic substitution of heteroaromatic compounds, 16, 123 Hydantoins, chemistry of, 38, 177 Hydrogen cyanide derivatives, synthesis of heterocycles from, 41, 1 Hydrogen exchange base-catalyzed, 16, 1 one-step (labeling) methods, 15, 137 Hydrogenated porphyrin derivatives hydroporphyrins, 43, 73 Hydroxamic acids, cyclic, 10, 199 1 -Hydroxyindoles, 1 -hydroxytryptophans, and 1-hydroxytryptamines,... 

These reactions have a general relevance in organic synthesis, as they allow the performance of X-methylation reactions such as cyano-, thio-, amidomethylations, etc. starting from hydrogen cyanide, amides, etc. When, in particular, the abovemen-tioned methylol derivatives are allowed to react with amine (R —YH = primary or secondary amine), a Mannich base is produced. 

The preparation of a formyl-substituted aromatic derivative 3 from an aromatic substrate 1 by reaction with hydrogen cyanide and gaseous hydrogen chloride in the presence of a catalyst is called the Gattermann synthesis This reaction can be viewed as a special variant of the Friedel-Crafts acylation reaction. 

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