Polymer-Supported Benzotriazoles as Catalysts in the Synthesis of Tetrahydroquinolines by Condensation of Aldehydes with Aromatic Amines

Abstract

Four polymer-supported benzotriazoles were prepared by linkage of 5-(hydroxymethyl)benzotriazole and benzotrizaole-5-carboxylic acid with Wang resin, Merrifield resin, and (monomethoxy)poly(ethylene glycol). The solid-phase and liquid-phase syntheses of tetrahydroquinolines were achieved by two-pair coupling reactions of aldehydes and aromatic amines using these polymer-supported benzotriazoles as the promoters. The ether-type benzotriazole prepared by loading 5-(hydroxymethyl)benzotriazole onto Merrifield resin turned out to be the catalyst of choice. Thus, a series of tetrahydroquinoline products were obtained in high purity by simple filtration, and the resin was recovered for reuse without loss of activity.

Simple and rapid detection of aromatic amines using a thin layer chromatography plate

“…The development of a fast and sensitive colorimetric sensor or reagent for detection and identification of ions [1][2][3][4][5][6][7] and small molecules [8][9][10][11][12] has emerged as an actively investigated area of research in recent years. Aromatic amines are one of the most important compounds and are used widely, not only in the synthesis of drugs [13][14][15][16][17] and pesticides [18][19][20][21][22][23] as key structure units, but also in the field of polymer materials chemistry. [24][25][26][27][28] However, a number of aromatic amines have recently been found to be carcinogens [29][30][31][32][33] and have been polluting the human environment [34][35][36] including food and water.…”

Benzotriazole: An overview on its versatile biological behavior

“…Some authors have also reported the synthesis of stable nitrenium ions using BT as synthon [19]. Polymer-supported benzotriazoles were also used as catalysts for the generation of a tetrahydroquinoline library [20].…”

Simple and Efficient Method for the Synthesis of Highly Substituted Imidazoles Catalyzed by Benzotriazole

“…The use of organic molecules as catalysts has provided attractive alternatives to the more traditional metal‐catalyzed. In recent years, benzotriazole has wide application as a synthetic auxiliary in a multitude of synthetic endeavors , such as nitrogen ligand, reactive promotion reagents, or catalyst. But it has not been studied as a catalyst in the synthesis of imidazoles until now.…”