The synthesis of the new compounds (7-chloroquinolin-4-yl)-N′-(1′-dimethylaminomethylferrocen-1-ylmethyl)-amine (4a) and N-(7-chloroquinolin-4-yl)-N′-(1′-dimethylaminomethylferrocen-1-ylmethyl)-ethane-1,2-diamine (6a) is reported. The key step in the synthesis is the cleavage of a ferrocene–Sn bond with n-BuLi to give a lithiumferrocenide species (10), which is then treated with an electrophile. Thus, 1′-dimethylaminomethyl-1-tri-n-butylstannyl-ferrocene (11) and subsequently 1′-dimethylaminomethylferrocene-1-carbaldehyde (7a) were synthesised from 1,1′-bis(tri-n-butylstannyl)ferrocene, employing [CH2 NMe2]I and DMF to introduce the amine and then the aldehyde functionalities. In addition, the compound 1′-dimethylaminomethyl-1-lithiumferrocenide was isolated and the 1H and 13C NMR data are reported. X-Ray crystal and molecular structures are reported for compound 4a and the related compound N-(7-chloroquinolin-4-yl)-N′-(2-dimethylaminomethylferrocen-1-ylmethyl)-ethane-1,2-diamine (5a). The antiplasmodial activity in vitro against chloroquine sensitive and resistant strains of Plasmodium falciparum is reported and compared to a series of ferrocene, ruthenocene and phenylene analogues.
It is widely accepted in the higher education literature that a student-centred approach is pedagogically superior to a teacher-centred approach. In this paper, we explore the notion of student-centredness as a threshold concept and the implications this might have for academic staff development. We argue that the term student-centred in the Rogerian sense implies a focus on the person of the student and is deeply resonant with Barnett's assertion that the emergent being of the student is as important as the development of skills and knowledge. To facilitate transformative learning in higher education an academic must know how to value the person of the student in the learning process. Academic staff development initiatives need to work with the person of the academic and take into account the level of personal development required for each academic to be able to facilitate this kind of learning.
25 August 2014 in Chemistry Education Research and Practice
This is a conceptual paper aimed at chemistry educators. The purpose of this paper is to illustrate the use of the semantic code of Legitimation Code Theory in chemistry teaching. Chemistry is an abstract subject which many students struggle to grasp. Legitimation Code Theory provides a way of separating out abstraction from complexity both of which provide substantial challenges to students. These are termed semantic gravity (degree of abstraction) and semantic density (degree of complexity). These ideas are then illustrated using chemical examples in order to demonstrate how they may aid the teaching of chemistry. There is a second pedagogical device which Maton, the developer of Legitimation Code Theory, calls ‘semantic waves’. This is also discussed in the context of chemistry education. The semantic code could be applied to chemistry at all levels.
The syntheses of the new compounds (7-chloroquinolin-4-yl)(2-dimethylaminomethylruthenocen-1-ylmethyl)amine 3 and N-(7-chloroquinolin-4-yl)-N′-(2-dimethylaminomethylruthenocen-1-ylmethyl)ethane-1,2-diamine 5 are reported. The reactions are compared to those previously reported for the preparation of the ferrocene analogues. The key step in the reaction is the regioselective synthesis of 2-dimethylaminomethylruthenocene carboxaldehyde 10 by deprotonation of dimethylaminomethylruthenocene with t-BuLi in diethyl ether, followed by the addition of DMF. In addition, 1′-dimethylaminomethylruthenocene carboxaldehyde 11 was also prepared leading to the unexpected synthesis of the 1,1′-isomers (7-chloroquinolin-4-yl)(1′-dimethylaminomethylruthenocen-1-ylmethyl)amine 17 and N-(7-chloroquinolin-4-yl)-N′-(1′-dimethylaminomethylruthenocen-1-ylmethyl)ethane-1,2-diamine 18. X-Ray crystal and molecular structures for compounds 3 and 17·H2O are reported. The 4-aminoquinoline complexes show high efficacy against the chloroquine sensitive and resistant strains of the Plasmodium falciparum parasite in vitro; these results are compared with those obtained for the analogous ferrocene compounds.
1 October 2007 in Bioorganic & Medicinal Chemistry