Fatiha Belferdi, Naima Merabet, L. Belkhiri
Aug 15, 2016
Citations
0
Influential Citations
7
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract Demethylation of compound 2,7-dimethoxyquinoline-3-carbaldehyde 1 , is carried out using BBr 3 . However, all attempts led, either to the starting material or to the regioselective demethylation at position 2 affording the product 4a . The nature (donor or acceptor) and the position of the R (CHO or CN) group is likely to play a role in the preventing the demethylation at position 7. To address this phenomena, the demethylation of 2-chloro-7-methoxyquinoline-3-carbaldehyde 2 and 2,7-dimethoxyquinoline-3-carbaldehyde 3 has been carried out. To support the results obtained, theoretical computations at DFT level (vide infra) have been carried out upon compound 1 . The exploration of how the gas-phase demethylation process on Quinoline can be affected at a position 7 center by stepwise substation effects using different electro-donor and attractor groups, show that demethylation process seems to be more favorable when substituent is an electro-donor. This is sustained by bond energy and thermodynamic analyses (vide infra).