2-(Azolyl)anilines: methods of synthesis, cyclocondensations, and biological properties

Abstract

This review offers summary and analysis of the data on the synthesis of 2-(azolyl)anilines published from 1942 to 2016. It is shown, that they act as effective 1,5-nucleophiles in cyclocondensation reactions. Besides, biological activity data on 2-(azolyl)anilines and their derivatives are reported.

Tandem heterocyclization of 2‐(azolyl‐(azinyl‐))anilines as an efficient method for preparation of substituted pyrrolo[1,2‐a]azolo‐(azino‐)[c]quinazolines

“…In the same time, the reaction of compounds 1‐3 with ethyl chloroformate, N , N ′‐carbonyldiimidazol, carbon disulfide, and sodium (potassium) O‐methyl carbonodithioates yielded dihydroazolo‐(azino‐)[ c ]quinazoline‐ones(thiones) . The usage of carbonyl‐containing compounds and their synthetic equivalents (aldehydes, ketones, paraform, acetals, and aldehydo acids) as electrophiles allowed to obtain partially hydrogenated or spiro‐condensed analogues . Similar results, namely, formation of 6,7‐dihydro‐2 H ‐[1,2,4]triazino[2,3‐ c ]quinazolines, were observed in the reaction of substituted 3‐(2‐aminophenyl)‐6‐ R ‐1,2,4‐triazin‐5(2 H )‐ones with DMAD, whereas reaction of 3‐(2‐aminophenyl)‐6‐ R ‐1,2,4‐triazin‐5(2 H )‐ones with о‐formylbenzoic and opianic acid occurred as tandem formation of pyrimidine and isoindole fragments that yielded corresponding isoindolo[2,1‐ a ][1,2,4]triazino[2,3‐ c ]quinazolines .…”

“…The structures of heterocycles resulting from modification of the abovementioned initial compounds depend on the nature of electrophilic reagents as well as on the reaction conditions. Thus, compounds 1‐3 in [5 + 1]‐cyclocondensation with acylating agents yielded aromatic tricyclic systems . In the same time, the reaction of compounds 1‐3 with ethyl chloroformate, N , N ′‐carbonyldiimidazol, carbon disulfide, and sodium (potassium) O‐methyl carbonodithioates yielded dihydroazolo‐(azino‐)[ c ]quinazoline‐ones(thiones) .…”

“…Thus, compounds 1‐3 in [5 + 1]‐cyclocondensation with acylating agents yielded aromatic tricyclic systems . In the same time, the reaction of compounds 1‐3 with ethyl chloroformate, N , N ′‐carbonyldiimidazol, carbon disulfide, and sodium (potassium) O‐methyl carbonodithioates yielded dihydroazolo‐(azino‐)[ c ]quinazoline‐ones(thiones) . The usage of carbonyl‐containing compounds and their synthetic equivalents (aldehydes, ketones, paraform, acetals, and aldehydo acids) as electrophiles allowed to obtain partially hydrogenated or spiro‐condensed analogues .…”

“…Considering the originality of mentioned reaction, the study of 2‐(azolyl‐(azinyl‐))anilines reactivity relative to such electrophiles as 4‐ R ‐4‐oxocarboxylic acids is quite interesting. Moreover, obtained polycyclic products are promising as bioactive agents with anticancer, antibacterial, antiviral, hypoglycemic, hypolipidemic, anticonvulsant, etc activities …”

Directed Search of Biologically Active Compounds among Hydrogenated Isoindolylalkyl(alkylaryl-,aryl-)carboxylic Acids with Quinazoline Fragment that Modify the Carbohydrate Metabolism: Design, Synthesis and Modification

“…Quinazoline derivatives and their condensed analogues have always attracted the attention of medicinal chemists as objects of advanced research, aimed at the elaboration of new drugs. This fact is explained by the high biological activity of natural, [1][2][3] as well as synthetic quinazolines [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] and, undoubtedly, their wide ability to chemical modification. [10][11][12][13]18 In recent years, the interest for this heterocyclic system has increased greatly since the introduction of in silico approaches to the drug search strategy, combinatorial chemistry and high-throughput screening.…”