Alkylation and Related Electrophilic Reactions at Endocyclic Nitrogen Atoms in the Chemistry of Tetrazoles

Acid Catalyzed tert‐Butylation and Tritylation of 4‐Nitro‐1,2,3‐triazole: Selective Synthesis of 1‐Methyl‐5‐nitro‐1,2,3‐triazole via 1‐tert‐Butyl‐4‐nitro‐1,2,3‐triazole

“…It should be noted that this reaction is a new example of selective alkylation of azoles with alcohols in acidic medium. Previously regioselectivity was also observed under alkylation of 5‐ R ‐tetrazoles and some 1,2,4‐triazoles in analogous conditions . Parent 1,2,3‐triazole was found to react with isopropanol in concentrated sulfuric acid giving only 1‐isopropyl‐1,2,3‐triazole as reaction product .…”

“…It should be noted that this reaction is a new example of selective alkylation of azoles with alcohols in acidic medium. Previously regioselectivity was also observed under alkylation of 5-R-tetrazoles and some 1,2,4-triazoles in analogous conditions [7,8].…”

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

“…Similar analysis for 12 indicated no such correlation. In order to try and improve the N 1 -PMB/N 2 -PMB ratio, converting 5 to a triethylammonium salt form in 94% yield was adopted [18]. Subsequent reaction with PMBCl gave 11 and 12, but in a largely unchanged ratio (N 1 -PMB/N 2 -PMB = 1:1.1).…”

Microwave-assisted efficient one-pot synthesis of N2-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

“…They play an important role not only as a bioisostere of the carboxylic acid group but also as flexible ligands which easily adopt to different binding modes [12,13]. Tetrazole derivatives exhibit a wide spectrum of biological activities as antibacterial [14], anticancer [15], anti-inflammatory [16], antidiabetic [17], antitubercular [18], and analgesic [19] agents. It is well established that many medical disorders can be caused as a result of defects at more than one specific biological target such as a receptor or an enzyme.…”