2-cyano-3-hydroxypyridine

The synthesis of the tetracyclic pyrido[3,2- >]furo [3,2-6Jbenzo[l,4j-diazepinone (47) starting with 2-cyano-3-hydroxypyridine (42) and 3-... 

Reaction of anthranilic acid and 2-chloro-5-cyano-4-hydroxypyridin-6(l//)-one in glacial acetic acid for 18 h gave 8-cyano-7-hydroxy-5,9-dihydro-11 //-pyrido[2,l-6]quinazoline-9,l 1-dione (45). When the reaction was carried out in dimethylformamide under Ullmann conditions, 5-cyano-2-dimethylamino-4-hydroxypyridin-6-one also formed as a by-product... 

The molecular structure of B after irradiation is shown in Fig. 21. Only the 1-cyanoethyl group was changed after irradiation. The inverted 1-cyanoethyl group takes a different conformation from those observed in the piperidine and pyrrolidine crystals the methyl group is replaced with the cyano group in the alaninate crystal, whereas the methyl group is replaced with the hydrogen atom in the piperidine and pyrrolidine crystals. Such an inversion mode has been found only in a crystal of (l-cyanoethyl)(3-hydroxypyridine)cobaloxime [42]. 

C8H8N20 3-cyano-4,6-dimethyl-2-hydroxypyridine 769-28-8 25.00 1.1781 2 13469 C8H803 methyl 4-hydroxybenzoate 99-76-3 47.17 1.2172 2... 

Bifunctional catalysis. Some time ago Swain and Brown1 observed that 2-hydroxypyridine catalyzed the mutarotation of tetramethylglucose by a concerted base-acid catalysis and that it is more effective than pyridine plus phenol. A few years later Beyerman and van den Brink2 showed that 2-hydroxypyridine and other bifunctional compounds catalyze the reaction of amines with cyano-methyl esters (reactive esters) as well as low-energy esters in peptide synthesis. Pyrazole and 1,2,4-triazole (1,1188), were equally effective. 

If the oxazole contains cyano or alkoxy groups in the 5-position, or if the dienophile possesses appropriate leaving groups, then these groups can be eliminated and 3-hydroxypyridines are formed. The industrial synthesis of pyridoxine 27 (vitamin B, see p 305) is based on these reactions. 

High level production of 3-cyano-6-hydroxypyridine from... 

Comments on the diazotization of aminopyridines and their 1-oxides have been made in connection with nucleophilic substitutions leading to cyano-(p. 226), halogeno- (p. 229) and hydroxy-pyridines (p. 239). The formation of a diazotate from 2-aminopyridine (p. 229), and of diazo oxides from 3-amino-2- and -4-hydroxypyridine (p. 270) has also been noted. 

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