@article {828, title = {A one-pot synthesis and X-ray crystallographic and computational analyses of methyl-2,4-dimethoxysalicylate - a potential anti-tumour agent}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {82}, number = {7}, year = {2004}, note = {ISI Document Delivery No.: 861XBTimes Cited: 5Cited Reference Count: 34}, month = {Jul}, pages = {1179-1185}, type = {Article}, abstract = {The thermal decarboxylation of 2-methoxycarbonyl-5-(4{\textquoteright}-nitrophen-oxy)tetrazole (1a) with the electron-rich, aromatic compounds (anisole, N,N-dimethylaniline, 1,4-dimethoxybenzene, and 1,3,5-trimethoxybenzene), neat or in polar solvents (DMSO, DMF, and CH3CN), is investigated. The solid phase thermal decomposition of a mixture of 1a, 1,3,5-trimethoxybenzene, and a Lewis acid (AlCl3) produces methyl-2,4-dimethoxysalicylate (8) in good yield, instead of the expected 2,4,6-trimethoxybenzoic acid. The X-ray structure of 8 shows intramolecular hydrogen bonds between the carbonyl oxygen and hydrogens of Me and OH groups. A measured pK(a) value of 6.8 compares well with a value of 6.4 estimated using the [C=O...H...O] hydrogen bond distances.}, keywords = {2{\textquoteright}, 6{\textquoteright}-DIMETHOXYFLAVONE, ACID, anti-tumor, computational analysis, hydrogen bonds, HYDROGEN-BOND DATA, novel synthesis, PK(A), TETRAZOLES, X-ray structure}, isbn = {0008-4042}, url = {://000224450800007}, author = {Dabbagh, H. A. and Noroozi-Pesyan, N. and Patrick, B. O. and James, Brian R.} }