Efficient electrosynthesis of 1,2,4-triazino[3,4-b]-1,3,4-thiadiazine derivatives

Fotouhi, Lida; Mosavi, M.; Heravi, Majid M.; Nematollahi, Davood

doi:10.1016/j.tetlet.2006.09.137

Cited by 33 publications

(23 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Electrochemical oxidation of catechols (1) in water containing phosphate buffer (pH = 7.0) in the presence of 4-amino-6-methyl-1,2,4-triazine-3-thion-5-one (79) [89], 4-amino-3-thio-1,2,4-triazole (80) [90] and 2-thiouracil (81) [91] as nucleophiles are other examples of an ECEC mechanism with C-S and C-N bond formation (see Table 4). Also the oxidation of C-3 substituted catechols in the presence of 2- [24] mercapto-4-(3H)-quinazolinone (17) proceeds via an ECEC mechanism [24].…”

Section: C-n C-s Bond Formationmentioning

confidence: 99%

“…Electrochemical oxidation of catechols (1) in the presence of barbituric acid (87a), 1,3-dimethylbarbituric acid (87b) and 1,3-diethyl-2-thiobarbituric (87c) is an example of ECEC 2 mechanism, in which the starting materials are converted to dispiropyrimidine derivatives (89). The electrochemical synthesis of products has been successfully performed in an undivided cell in good yield and purity.…”

Section: Ecec 2 Mechanismmentioning

confidence: 99%

See 1 more Smart Citation

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Nematollahi

Rafiee

Fotouhi

2009

JICS

Self Cite

View full text Add to dashboard Cite

The electrochemical oxidation of catechols was described and has shown that these compounds can be oxidized to related obenzoquinones. The electrochemically generated o-benzoquinones are quite reactive and can be attacked by a variety of nucleophiles under various mechanistic disciplines such as CE, EC, EC ' , ECE, ECEC, ECEC 2 , ECECE, ECECEC, ECECECE and trimerization, in which E represents an electron transfer at the electrode surface, and C represents a homogeneous chemical reaction. The mechanistic pathways and final products are depending on some parameters such as electron withdrawing or donating properties of nucleophile, electrolysis medium (solvent, acidity or pH) and nature of catechol.

show abstract

Section: C-n C-s Bond Formationmentioning

confidence: 99%

Section: Ecec 2 Mechanismmentioning

confidence: 99%

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Nematollahi

Rafiee

Fotouhi

2009

JICS

Self Cite

View full text Add to dashboard Cite

show abstract

“…Most of them have been shown to possess diverse biological activities [2][3][4][5], such as antibacterial, antifungal, antithyroid, hypoglycaemic and antidepressant Schiff bases also constitute a good type of biologically active substructure. Studies of pyrazole Schiff base-type fungicides and triazole compounds containing the hydrazonecarbonyl group have been reported [6].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-4-(benzylideneamino)-3-(2-ethoxyphenyl)1H-1,2,4-triazole-5(4H)-thione, C17H16N4OS

Ding¹,

Huangi²,

Sun³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

C17H16N4OS, monoclinic, P\2\k\ (no. 14), a = 7.9578(9) Â, b = 15.466(2) Â, c = 13.964(2) k,ß = 92.177(2)°, V= 1717.3 Â 3 , Ζ = 4, R gt (F) = 0.073, = 0.168, Γ =273 Κ. Source of materialThe title compound was prepared by the reaction of 4-amino-3-(2-ethoxyphenyl)-liM,2,4-triazole-5(4//)-thione (0.002 mol) and benzaldehyde (0.002 mol) with a little concentrated hydrochloric acid in ethanol (20 ml). The mixture was refluxed for 3 h and the solid obtained on cooling was filtered, washed with cold water, dried and recrystallized from ethanol to give the title compound. The purified product was dissolved in ethanol and single crystals were obtained after 5 days by slow evaporation of the ethanol solution at room temperature. The key intermediate triazole was prepared from 2-ethoxybenzoic acid hydrazide (prepared from 2-ethoxybenzoic acid), following the literature method of [1]. Experimental detailsThe HI atom was refined subject to the restraint d{Ν-Η) = 0.85(3) Â. The other H atoms were positioned geometrically and alio wed to ride on their parent atoms at distances of d(Csp 2 -H) = 0.93 Â with i/iso = 1.2 i/eq(parent atom), and d(Csp 3 -H) = 0.96 or 0.97 Â with i/iso =1.5 l/eq(parent atom). The huge R values may be attributed to the weak diffraction intensity of the sample crystal. DiscussionHeterocyclic compounds containing a 1,2,4-triazole group have attracted considerable attention over the past two decades. Most of them have been shown to possess diverse biological activities [2][3][4][5], such as antibacterial, antifungal, antithyroid, hypoglycaemic and antidepressant Schiff bases also constitute a good type of biologically active substructure. Studies of pyrazole Schiff base-type fungicides and triazole compounds containing the hydrazonecarbonyl group have been reported [6]. In the title crystal structure, the bond lengths and angles are usual. The five-membered triazole ring and two benzene rings are each essentially planar. The triazole and the benzene ring (C1-C6) make a dihedral angle of 57.3(1)°, and the dihedral angle between the triazole and the benzene ring (C10-C15) is 34.3 (2)°. Both the S-C and C-Ν bond lengths are in good agreement with the values observed in related compounds. The short C-Ν bond lengths of 1.294(3) A for NI-C7 and 1.251(3) Â for N4-C9 [7][8][9], respectively, suggest partially localized double bonds.

show abstract

“…Clean synthesis, use of electricity as energy instead of oxidative reagents, use of aqueous media instead of organic solvents, one step reactions, operation at room temperature and pressure, technical feasibility, and especially high atom economy are among preeminent green advantages [1]. Electrosynthesis can lead to efficient and sometimes unexpected synthesis of compounds, which cannot be easily prepared by conventional organic synthesis [2].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical study of catechols in the presence of 2-thiazoline-2-thiol: application to electrochemical synthesis of new 4,5-dihydro-1,3-thiazol-2-ylsulfanyl-1,2-benzenediol derivatives

et al. 2008

View full text Add to dashboard Cite

Electrochemical oxidation of catechols (1a-d) has been studied in the presence of 2-thiazoline-2-thiol (3) as a nucleophile in aqueous solution, using cyclic voltammetry and controlled potential coulometry. The results indicate that the quinones derived from catechols (1a-d), participate in Michael addition reactions with 2-thiazoline-2-thiol and via an EC mechanism pathway, convert to the corresponding catechols derivatives (4a-d and 4 0 d). The electrochemical synthesis of compounds (4a-d and 4 0 d) has been successfully performed at a carbon rod electrode and in an undivided cell with good yield and high purity. The products have been characterized by IR, 1 H NMR, 13 C NMR and MS.

show abstract

Efficient electrosynthesis of 1,2,4-triazino[3,4-b]-1,3,4-thiadiazine derivatives

Cited by 33 publications

References 13 publications

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Mechanistic study of homogeneous reactions coupled with electrochemical oxidation of catechols

Crystal structure of (E)-4-(benzylideneamino)-3-(2-ethoxyphenyl)1H-1,2,4-triazole-5(4H)-thione, C17H16N4OS

Electrochemical study of catechols in the presence of 2-thiazoline-2-thiol: application to electrochemical synthesis of new 4,5-dihydro-1,3-thiazol-2-ylsulfanyl-1,2-benzenediol derivatives

Contact Info

Product

Resources

About