1458712-46-3Relevant academic research and scientific papers
Tuning the ring-chain tautomerism of a tetrahydroquinazoline/Schiff base system with unexpected methanol oxidation
Sanmartín-Matalobos, Jesús,Portela-García, Cristina,García-Deibe, Ana M.,Fondo, Matilde,Briones-Miguéns, Lucía
, p. 181 - 186 (2013)
The ring-chain tautomerism of a tetrahydroquinazoline/Schiff base (H 2Lring/H2Lchain) system can be controlled by metal coordination through varying ligand stoichiometry of the reaction H2L + M2+ [H2Lring: 2-(3-tosyl-1,2,3,4-tetrahydroquinazolin-2-yl)quinolin-8-ol; H2L chain: N-{2-[(8-hydroxyquinolin-2-yl)methyleneamino]benzyl}-4- methylbenzenesulphonamide and M: Co2+ and Cd2+]. The ring tautomer H2Lring undergoes a ring-opening reaction upon formation of dinuclear complexes M2(Lchain)2, while Co2+ and Cd2+ stabilise the tetrahydroquinazoline ligand in their mononuclear complexes M(HLring)2. The detection of 3-tosyl-1,2,3,4-tetrahydroquinazoline on the methanolic mother liquors of Co2(Lchain)2 revealed the acid-catalysed hydrolysis of the Schiff base ligand and the cobalt-mediated aerobic oxidation of methanol to formaldehyde.
Serendipitous formation of 3-tosyl-1,2,3,4-tetrahydroquinazoline
Sanmartin-Matalobos, Jesus,Garcia-Deibe, Ana M.,Briones-Miguens, Lucia,Lence, Emilio,Gonzalez-Bello, Concepcion,Portela-Garcia, Cristina,Fondo, Matilde
, p. 3043 - 3049 (2013)
Both experimental and computational studies were undertaken to elucidate the formation process of 3-tosyl-1,2,3,4-tetrahydroquinazoline from methanolic mother liquors of Pd(LBS)·3H2O, where L BS is the dianionic form of th
Dual role of 2-tosylaminomethylaniline as a ligand and a nucleophile in the copper-mediated oxidation of methanol
Sanmartin-Matalobos, Jesus,Garcia-Deibe, Ana M.,Briones-Miguens, Lucia,Gonzalez-Bello, Concepcion,Portela-Garcia, Cristina,Fondo, Matilde
, p. 722 - 728 (2014)
Some reactivity in the oxidation of methanol to formaldehyde has been spectroscopically detected on the methanolic mother liquors of a copper(ii) complex of a Schiff base ligand derived from the condensation of 8-hydroxyquinoline-2-carboxaldehyde and 2-tosylaminomethylaniline. An investigation has shown that 2-tosylaminomethylaniline (HATS) plays a dual role in the oxidative process acting as a N-donor ligand and reacting in situ with formaldehyde, which leads to 3-tosyl-1,2,3,4-tetrahydroquinazoline (1). This was characterized by using both spectroscopic and X-ray diffraction techniques. The influence of 8-hydroxyquinoline derivatives, water and ligand stoichiometry on the yield of 1 was studied.
