155431-49-5Relevant academic research and scientific papers
Interaction of aryl tetrazolones with anions: proton transfervs.hydrogen bonding
Nord, Erika,Rayat, Sundeep,Zhou, Hanyang
supporting information, p. 14184 - 14192 (2021/08/16)
In this study, the interaction of two monosubstituted aryl tetrazolones, namely 1-(4-nitrophenyl)-1,4-dihydro-tetrazol-5-one1aand 1-(4-trifluoromethylphenyl)-1,4-dihydro-tetrazol-5-one1b, with anions of varying basicitye.g.hydrogen sulfate (HSO4?), bromide (Br?), nitrate (NO3?), thiocyanate (NCS?), chloride (Cl?) and acetate (AcO?) was investigated in acetonitrile and DMSO. UV and NMR titrations indicated that tetrazolones interact through hydrogen bonding or weak electrostatic interactions with HSO4?, Br?, NO3?, NCS?, and Cl?. The association constants (Ka) were found to be in the order Cl?> Br?> NO3?> NCS?> HSO4?. Tetrazolones1a,bexhibited almost 9 times higher selectivity towards Cl?compared to Br?which may be attributed to the higher basicity of the former. The affinity of1atowards most anions was higher than1b, except for HSO4?. This was attributed to the higher electron withdrawing ability of the -NO2group compared to -CF3that renders the N-H proton more acidic for interaction with anions resulting in higherKavalues. Significant UV changes were observed upon addition of the AcO?anion to the solution of1a,bin acetonitrile as new bands formed and isosbestic points were observed indicating the formation of a new species. NMR titrations in DMSO-d6further confirmed that1a,bunderwent deprotonation with AcO?owing to its higher basicity.
A facile route for the synthesis 1,4-disubstituted tetrazolone derivatives and evaluation of their antimicrobial activity
Santhoshi, Amlipur,Sadhu, Partha Sarathi,Sriram, Rekulapally,Sai Pavan Kumar, Chebolu Naga Sesha,Mahendar, Budde,Sarangapani, Manda,Rao, Vaidya Jayathirtha
, p. 3329 - 3340 (2013/07/19)
A facile route for the synthesis of 20 new 1,4-disubstituted tetrazolone derivatives from allyl bromides of Baylis-Hillman adducts and various 1-substituted tetrazolones is described. All the synthesized compounds were screened for in vitro antibacterial
Process for the preparation of 1-4-disubstituted-5 (4H)-tetrazolinones
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, (2008/06/13)
1,4-Disubstituted-5(4H)-tetrazolinones of the formula (I) STR1 wherein R1, R2 and R3 have the meanings given in the specification), which are known to be useful as herbicides, can be obtained in very good yields by reacting the corresponding 1-substituted-5(4H)-tetrazolinones with the corresponding carbamoyl chlorides in the presence of 4-dimethylaminopyridine.
Process for the preparation of 1-substituted-5(4H)-tetrazolinones
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, (2008/06/13)
A process for the preparation of a 1-substituted-5(4H)-tetrazolinone of the formula STR1 wherein R1 is defined in the specification n is 0, 1, 2, 3 or 4, which comprises reacting a 1-substituted-5(4H)-tetrazolinethione of the formula STR2 with an ethylene oxide of the formula STR3 wherein R2 represents hydrogen, methyl or ethyl, in the presence of a base and in the presence of water, an alcohol or a mixture thereof.
Optically active antifungal azoles. VI. Synthesis and antifungal activity of N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones and 5(1H,4H)-tetrazolones
Kitazaki, Tomoyuki,Tamura, Norikazu,Tasaka, Akihiro,Matsushita, Yoshihiro,Hayashi, Ryogo,Okonogi, Kenji,Itoh, Katsumi
, p. 314 - 327 (2007/10/03)
A new series of optically active antifungal azoles, N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl) propyl]-N′-(4-substituted phenyl)-3(2H,4H)-1,2,4-triazolones (1,2) and 5(1H,4H)-tetrazolones (3), were prepared from the triflate derivative of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (13) by an SN2 displacement reaction with the union of an azolone (17-19) and subsequent ring-opening reaction with 1H-1,2,4-triazole. The optically active oxiranylethanol 13 was synthesized from methyl (R)-lactate in a stereocontrolled manner. The azolones 1-3 prepared showed potent antifungal activities in vitro and in vivo.
Azole compounds, their production and use
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, (2008/06/13)
An azole compound represented by the formula (I): STR1 wherein Ar is a substituted phenyl group; R1 and R2 independently are a hydrogen atom or a lower alkyl group, or R1 and R2 may combine together to form a lower alkylene group; R3 is a group bonded through a carbon atom; R4 is a hydrogen atom or an acyl group; X is a nitrogen atom or a methine group; and n Y and Z independently are a nitrogen atom or a methine group which may optionally be substituted with a lower alkyl group, or a salt thereof, which is useful for prevention and therapy of fungal infections of mammals as antifungal agent.
