190257-84-2Relevant articles and documents
Using iSUSTAIN to validate the chemical attributes of different approaches to the synthesis of tacn and bridged (bis)tacn ligands
Coghlan,Campi,Jackson,Hearn
, p. 5477 - 5484 (2016)
Using green chemistry principles, alternative approaches for the synthesis of commercially important aza-macrocyclic tacn and (bis)tacn derivatives have been investigated to determine the step average and overall efficiency of these synthetic methods. Based on analytical metrics derived from the iSUSTAIN toolkit, the Richman-Atkins route for the synthesis of tacn (1) was found to be the more efficient; however an alternate route was shown to be preferable for the synthesis of (bis)tacn (2) compounds. The outcome of this study documents the importance of rigorous analysis of synthetic procedures for such aza-macrocyclic compounds in terms of their green chemistry attributes, in order to delineate how alternative synthetic methods can be ranked, more innovative procedures selected to improve productivity and yield, and synthetic methods deployed to achieve greater levels of waste reduction, reduced use of hazardous chemicals and lower environmental impact.
An efficient route to symmetrically and unsymmetrically substituted azamacrocyclic ligands
Pulacchini, Sonia,Watkinson, Michael
, p. 4233 - 4238 (2007/10/03)
An extremely efficient cyclisation protocol has been developed for the synthesis of symmetrically (6) and unsymmetrically substituted (7) derivatives of 1,4,7-triazacyclononane (2). The optimised conditions can be successfully applied to the synthesis of larger macrocycles 15a and 18a. In contrast, the protocol is not generally applicable with benzylamine, and the cyclic carbamates 16 and 19, rather than larger azamacrocycles, are formed, indicating that cyclisation in CH3CN using K2CO3 is highly specific to the formation of 7.
