Nucleophile Substitutionen am 2‐Phenyl‐5‐chlormethyl‐tetrazol

Synthesis of 2-aryl-2H-tetrazoles via a regioselective [3+2] cycloaddition reaction

“…Lippmann et al . has developed a regioselective method for the construction of 2-aryl tetrazoles employing 2-(2-arylhydrazono)acetic acid and 1-azido-2,4,6-tribromobenzene 1 . Ito’s synthesis employs arylsulfonylhydrazones and arene diazonium salts but both of these strategies afford 2-aryl-5-carboxylatetetrazole and must be decarboxylated at 160 °C 2 .…”

Synthesis and Evaluation of Photoreactive Tetrazole Amino Acids

“…Since the synthesis of 2-phenyl-5-carboxylatetetrazole has been reported in the literature, we decided to employ this type of monoaryltetrazole to derive three tetrazole-containing alkyl halides (Scheme ). Starting from ethyl glyoxalate, Kakehi’s method rapidly gave rise to ethyl 2-phenyltetrazole-5-carboxylate ( 4a ) and ethyl 2-tolyl-tetrazole-5-carboxylate ( 5a ) in 60% and 41% yield, respectively.…”

“…For the type II tetrazole amino acid side chains, benzyl bromide 5b was derived in 91% yield by treating 5a with N -bromo succinimide (NBS) and benzoyl peroxide (BPO) in a straightfoward manner. Because simple 2-phenyltetrazole was shown to be photoreactive toward methyl acrylate in benzene, we decided to remove the ester group in 5a through decarboxylation and obtained the second benzyl bromide 6b in 49% yield by following an identical procedure as 5b (Scheme ).…”