Cinnamoylnitrile‐, pyran‐, and pyranopyrazole‐derivatives containing the salicylanilide moiety with anticipated molluscicidal activity

Abstract

The reaction of new cinnamonitriles containing the salicylyl moiety with active methylene reagents leads to the formation of the corresponding heterocycles. Their reaction with aniline yields the corresponding salicylanilide derivatives. The obtained pyrans and anilides were tested for molluscicidal activity.

Synthesis, reactions and applications of pyranotriazolopyrimidines

“…Treatment of 10-amino-10,11-dihydro-11-imino-3-methoxy-12-(p-tolyl)-12H-naphtho [2,1-b] Reaction of compounds 13a,b with acetyl chloride and ethyl cyano acetate at reflux the corresponding 2-methyl-14-(ptolyl or p-methoxyphenyl)-14H-naphtho- [2,1-b]pyrano [2,3-e] [1,2,4]triazolo [1,5-c] [1,5-c]pyrimidines (14e,f), respectively, were formed. Reaction of compounds 13a,b with diethyl oxalate and benzoyl chloride at reflux afforded the correspondding 2-ethoxycarbonyl 14g,h and 2-phenyl 14i,j derivatives.…”

“…In the next step, condensed the N 1 -tosylaminonaphtha pyrano [2,3- [1,2,4]triazolo [1,5-c]yrimidines (25a-m). The formation of compounds 21a and 25a-m can be explained by asequence of events via intermediates of type [C], formed in the reaction of N1-tosylaminonaphthopyrano [2,3-d]pyrimidines 24 with triethyl ortho-formate, followed by spontaneous ethyl 4-methyl benzenesulfonate elimination (Scheme 9).…”

“…When compound 60b was treated with methyl chloro formate for 30 min, the methoxycarbonyl derivative 66 was formed, while heating of compound 60b with methyl chloroformate under reflux for 6 h afforded [1,2,4] Refluxing of compound 75 with ethyl cyanoacetate in dioxane affords the pyranotriazolopyrimidine derivative 76c (Scheme 22).…”

“…The formation of 2-trichloromethyl 10-methyl-8,11 [1,2,4]triazolo [1,5-c]-pyrimidine (90) via the interaction of compound 84 with trichloroacetic acid in the presence of phosphoryl chloride under reflux, or trichloro-acetonitrile in absence of solvent under reflux was unsuccessful. But The pyrimidinium salt 89 only isolable product (Scheme 26).…”

“…Pyran derivatives have attracted a great deal of interest owing to their antimicrobial activity [1][2][3][4][5][6][7], inhibition of influenza, virus sialidase [8], mutagenic activity [9], activity as antiviral [10], anti-proliferaction agents [11], sex pheromones [12], antitumor [13] and anti-inflammatory agents [14].…”