Nitroazines. 12 Reaction of 6-nitroazolo[1,5-a]pyrimidines with acetonitriles

Transformations of 5‐nitropyrimidines

“…The above transformation of 5-nitropyrimidines into pyridines was used [97,98] in the course of studying the possible re-cyclizations of pyrimidine ring in to bicyclic [1,2,4] The possibility of 5-nitropyrimidine 199 transformation into substituted nitropyrimidine under the action of enamine is described in a short publication [101]. The authors chose an unusual macrocyclic enamine 200 including a cyclodecene core (Scheme 66).…”

Cyanoacetamides and their thio- and selenocarbonyl analogues as promising reagents for fine organic synthesis

“…Thus the condensations of sodium salts of 2-hydroxymethylidenecycloalkanones 155 with amides 1b,c occur regioselectively to give only one of two possible isomers, viz., 5,6-annelated 3-cyanopyridine-2(1H)-thiones 156a and -selenones 156b. 85, 387, 400 ± 406 Yet another example of high regioselectivity is the reaction of sodium salt of 2-formylquinuclidone (157) with cyanothioacetamide (1b), which affords only bridged 3-cyano-1,5-naphthyridine-2(1H)-thione (158). 407 Cyanothioacetamide has been used in the synthesis of steroids annelated with the pyridine ring.…”

“…The latter are converted into 7nitro-9-oxo-4,9-dihydroazolo[1,5-a]pyrido [2,3-d]pyrimidines 124 on subsequent treatment with sodium carbonate in ethanol and acidification with HCl. 158,159 Synthesis of 5-amino-4-cyano-1,2,3-thiadiazole (126) by the reaction of tosyl azide 125 with cyanothioacetamide (1b) has been described. 160 Later, 161 1,2,3-thiadiazolium bromides 127 were obtained by bromination of arylhydrazonocyanothioacetamides 16.…”