6773-32-6Relevant academic research and scientific papers
Reaction of 5-aryloxytetrazoles with dimethyl sulfoxide and DMSO-acetic anhydride. Structure and quantum-chemical calculations of 1- methylsulfanylmethyl-5-(4-nitrophenoxy)tetrazole
Dabbagh,Noroozi Pesyan,Bagheri,Takemo,Hayashi
, p. 1055 - 1063 (2005)
Decomposition of methyl 5-(4-nitrophenoxy)tetrazole-2-carboxylate in dimethyl sulfoxide at room temperature yields a mixture of 1- methylsulfanylmethyl-5-(4-nitrophenoxy)tetrazole, 1- and 2-methyl-5-(4- nitrophenoxy)tetrazoles, and 5-(4-nitrophenoxy)tetrazole. Methyl 5-aryloxytetrazole-2-carboxylates containing electron-donor substituents in the aryloxy group do not give rise to the corresponding products under analogous conditions. The reactions of 5-aryloxytetrazoles [Ar = 4-O2NC 6H4, C6H5, 2,6-(MeO) 2C6H3] with dimethyl sulfoxide in the presence of acetic anhydride lead to mixtures of 1- and 2-methylsulfanylmethyl-5- aryloxytetrazoles whose yield and ratio depend on the substituent in the aryloxy group. The structure of 1-methylsulfanylmethyl-5-(4-nitrophenoxy)tetrazole was studied by X-ray analysis, two-dimensional NMR spectroscopy (HSQC, HMBC, NOESY), and quantum-chemical methods (ab initio, AM1, PM3). A highly selective procedure was developed for the synthesis of 5-(4-nitrophenoxy)tetrazole.
CoFe2O4 nanoparticles as a magnetically recoverable and reusable catalyst for the synthesis of arylaminotetrazoles and 5-aryloxytetrazoles
Bahari, Siavash,Rezaei, Akbar
, p. 65 - 68 (2014/03/21)
An efficient and direct method is described for the synthesis of 5-arylamino-1H-tetrazoles (Isomer A) or 1-aryl-5-amino-1Htetrazoles (Isomer B) and 5-aryloxytetrazoles from arylcyanamides or cynates with nano CoFe 2O4 as a reusable a
A one-pot synthesis and X-ray crystallographic and computational analyses of methyl-2,4-dimethoxysalicylate - A anti-tumour agent
Dabbagh, Hossein A.,Noroozi-Pesyan, Nader,Patrick, Brian O.,James, Brian R.
, p. 1179 - 1185 (2007/10/03)
The thermal decarboxylation of 2-methoxycarbonyl-5-(4′-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 pKa value of 6.8 compares well with a value of 6.4 estimated using the [C=O...H...O] hydrogen bond distances.
Kinetics and mechanism of izomerization of N-alkoxycarbonyl-5-aroxytetrazoles
Dabbagh,Mansoori
, p. 1771 - 1781 (2007/10/03)
The kinetics and mechanism of the N2-N1-isomerization of 2-methoxycarbonyl-5-(p-X-phenoxy)-tetrazoles (X = H, CH3, NHCOCH3, Cl, Br, NO2) were studied by 1H NMR spectroscopy in a DMSO-d6-CDCl3 mixture (25: 75). The rate of isomerization of the N2-isomer into N1-isomer fit the first-order equation (after three half-conversion periods). The isomerization is accompanied by hydrolysis and decarboxylation. The Hammett plot of In(kXlkH) for the isomerization showed a good correlation with σ- values (p- = 1.33, r = 0.965). A poor correlation with σ values was obtained. The kinetic data, the effect of solvent polarity, the substituent effects, and the results of AM1 quantum-chemical calculations suggest an ionic mechanism of the isomerization in polar solvents and a concerted mechanism in nonpolar solvents.
