2009
DOI: 10.1055/s-0029-1217398
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Synthesis of a Novel Class of Azacrown Macrocycles and Lariat Crown Ethers Containing Two 1,2,4-Triazole Rings as Subunits

Abstract: S y n t h e s i s o f A z a c r o w n M a c r o c y c l e s a n d L a r i a t C r o w n E t h e r s Abstract: Azacrown macrocycles were prepared in 70-76% yield by the condensation reaction of 1,2-, 1,3-, and 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)alkanes with bisaldehydes in acetic acid under reflux. Reaction of two of these azacrown macrocycles with iodomethane and benzyl chloride furnished exclusively the target lariat macrocycles in good yields.

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Cited by 17 publications
(7 citation statements)
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“…17 Moreover, it has been indicated in several reports that bisheterocyclic compounds displayed much better antibacterial activity than mono-heterocyclic compounds. [18][19][20][21] In view of these observations, and also in continuation of our previous work on the synthesis of bis-heterocyclic compounds, [22][23][24][25] we now report the synthesis of some novel pyridine bis-1,2,4-triazoles and bis-1,3,4-thiadiazoles.…”
supporting
confidence: 53%
“…17 Moreover, it has been indicated in several reports that bisheterocyclic compounds displayed much better antibacterial activity than mono-heterocyclic compounds. [18][19][20][21] In view of these observations, and also in continuation of our previous work on the synthesis of bis-heterocyclic compounds, [22][23][24][25] we now report the synthesis of some novel pyridine bis-1,2,4-triazoles and bis-1,3,4-thiadiazoles.…”
supporting
confidence: 53%
“…Prompted by these observations and as a continuation of our research program on the synthesis of 1,2,4-triazole derivatives [17][18][19][20][21], herein we wish to disclose synthesis of some novel five memberd heterocycle derivatives via intramolecular cyclization reactions in good yield.…”
Section: Introductionmentioning
confidence: 99%
“…In continuation of our interst to develop the synthesis of new azathiacrown macrocycles and lariat ether [3,18], we report herein, a simple and efficient method for the regioselective synthesis of novel BiBLES 4a-e. In this article, we demonstrate a novel method to introduce 1,2,4-triazolo [3,4-b] [1,3,4]thiadiazines rings into macrocycles.…”
Section: Resultsmentioning
confidence: 99%