Synthesis of novel benzo‐substituted macrocyclic schiff bases containing two triazole rings

Abstract

A synthesis of a series of novel macrocyclic Schiff bases containing two triazole rings 10a,b, 11a,b, 34-37 in good yields by heating the appropriate bis-amines 1f, 6a,b, 31 with the corresponding bis-aldehydes 2, 9a,b, 29 in refluxing acetic acid under high dilution conditions was described. Attempts to synthesize macrocyclic Schiff bases containing pyridine and two triazole rings were also described.

Synthesis, Structural Characterization and Metal Inclusion Properties of 18‐, 20‐ and 22‐Membered Oxaazacyclophanes and Oxaazacalix[4]arene Analogues: Macrocyclic Amine and Schiff Base Receptors with Variable NxOy Donor Sets

“…[18][19][20] From the synthetic point of view, these compounds can be obtained by a variety of methods, which typically involve either the high-dilution principle or the template effect, in order to increase the yield of the cyclization step. [21][22] In the metal template synthesis approach, however, stable metal-complexed macrocycles can be generated, and removal of the metal can be a problem in this case. [23] A third synthetic method for macrocyclic enclosure is the high-pressure procedure.…”

Efficient Routes for the Synthesis of Novel Bis(s‐triazolo[3,4‐b][1,3,4]thiadiazines)

“…In connection with these findings and in continuation of our interest in the synthesis of bis(hetrocycles) [38][39][40][41][42][43][44][45][46], we describe herein simple and efficient routes for the synthesis of novel bis(s-triazolo [3,4-b] [1,3,4]thiadiazines) in which the triazolothiadiazines are linked to arene core either directly or via alkyl, ether, thioether, or amine linkages.…”

Synthesis of New Macrocyclic Schiff Bases Containing Pyrazole and Triazole as Subcyclic Units

“…Moreover, macrocyclic derivatives were also reported to possess diverse biological and pharmacological activities such as inhibitors of hepatitis C virus, feline immunodeficiency virus and HIV proteases, human cytomegalovirus and ß‐secretase , and other analogs were exhibited to be anti‐inflammatory and antibacterial properties . Among them, macrocyclic Schiff bases formed an important class of macrocyclic host systems, which was easily obtained by condensation of a diamine with a diformyl or diketo compounds, and the presence of the basic imine functionality offered an additional coordination or hydrogen‐bonding site .…”