Influence of structure on the isomerization of dialkylaminoalkylbenzotriazoles

Abstract

The N‐1 to N‐2 substituent isomerization in a series of 4‐methyl and 4,7‐dimethyl‐N‐(α‐morpholinoalkyl)benzotriazoles and in 1,5‐bis(morpholinomethyl)benzo [1,2‐d:4,5‐d′] bistriazole was studied and the influence of the structure on this process was evaluated.

Properties and Synthetic Utility ofN-Substituted Benzotriazoles

“…In contrast, the bulkier the (dialkylamino)alkyl (or aryl) substituent, the more abundant the 2 isomers, which in extreme cases can become the predominant components. Ring substitution at the 4 or 4,7 positions of the benzotriazole ring also favors the 2 isomer …”

Selective Synthesis of N-H and N-Aryl Benzotriazoles by the [3 + 2] Annulation of Sodium Azide with Arynes

“…FTIR (cm −1 ) 3387, 2913, 2243, 1708, 1430, 1204triazole (2e). 23 Colorless solid, 30 mg in 0.5 mmol scale, 41% yield. Melting point: 169−171 °C.…”

Amino(hetero)arylmethylation of Phenols with N-[α-Amino(hetero)arylmethyl]benzotriazoles

“…Benzotriazole methodology, using reagents of the type RCH(NR 1 2 )Bt (Bt = 1-benzotriazolyl), has allowed extensions of Mannich aminomethylation to the general α-aminoalkylation of ketones, 2a,b esters and aliphatic nitro compounds . The present paper describes our attempts to similarly extend the well-known Mannich aminomethylations of phenols to the analogous α-aminoalkylations.…”