On triazoles. V. Synthesis of 1‐ and 2‐R1‐3‐R2,R3‐amino‐5‐amino‐1,2,4‐triazoles

Reiter, J.; Pongo, L.; Somorai, Tamás; Dvortsak, P.

doi:10.1002/jhet.5570230218

Cited by 45 publications

(9 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The values of the chemical shifts of the triazole ring carbon atoms in the 13 C NMR spectra of compounds 2b,c,f-h (C-3 155-158 and C-5 154 ppm) are close to those of other 1-R-3,5-diamino-1,2,4-triazoles [8,15]. In the proton-coupled 13 C NMR spectra the signal for the C-3 atom is split due to spin-spin coupling interaction through three bonds with the alkyl group protons to a triplet in compounds 2b,c,f,h (J = 3.5-4.1) and to a quartet in the methyl derivative 2g (J = 2.9 Hz) while the signal for the C-5 atom is a singlet (spin-spin interaction of the carbon nucleus with amino group protons not being observed due to rapid exchange of these protons with the solvent [15,16]).…”

mentioning

confidence: 64%

“…The C (3) N (4) C (4) O (1) C (5) fragment is planar to within ± 0.01 Å and the torsional angle C (4) -N (4) -C (1) -N (2) is 7.9(4)º. Angle The C (6) N (5) C (7) O (2) C (8) fragment is also planar to within ± 0.05 Å but it is twisted relative to the triazole ring plane as a result of a repulsive interaction between the acetyl group and the benzene ring (torsional angle C (7) -N (5) -C (2) -N (3) -68.2(4) Å). A shortened intramolecular contact for H(C (8) )···C (9) of 2.60 Å is observed in the molecule.…”

Section: Dmsomentioning

confidence: 98%

“…Angle The C (6) N (5) C (7) O (2) C (8) fragment is also planar to within ± 0.05 Å but it is twisted relative to the triazole ring plane as a result of a repulsive interaction between the acetyl group and the benzene ring (torsional angle C (7) -N (5) -C (2) -N (3) -68.2(4) Å). A shortened intramolecular contact for H(C (8) )···C (9) of 2.60 Å is observed in the molecule. Hence the acyl and sulfonyl fragments in the molecules 1a-c and 3 take the role of activating groups and this results in a regioselective alkylation of the N-anions formed in basic medium from the amide (sulfamide) group.…”

Section: Dmsomentioning

confidence: 98%

“…In the proton-coupled 13 C NMR spectra the signal for the C-3 atom is split due to spin-spin coupling interaction through three bonds with the alkyl group protons to a triplet in compounds 2b,c,f,h (J = 3.5-4.1) and to a quartet in the methyl derivative 2g (J = 2.9 Hz) while the signal for the C-5 atom is a singlet (spin-spin interaction of the carbon nucleus with amino group protons not being observed due to rapid exchange of these protons with the solvent [15,16]). Hence one can exclude a 4-alkyl-substituted alternative structure since a splitting of the C-5 signal due to 437 interaction with alkyl group protons would be observed [8,16]. In addition, compounds 2d,h are identical to those synthesized in the study [12].…”

mentioning

confidence: 99%

See 3 more Smart Citations

Alkylation of acyl and sulfonyl derivatives of 3,5-diamino-1-phenyl-1,2,4-triazole

Чернышев

Rakitov

Blinov

et al. 2009

Chem Heterocycl Comp

View full text Add to dashboard Cite

structural analysis, structure.Alkylation of C-amino-1,2,4-triazoles by alkyl halides and alkyl sulfates usually occurs at the nitrogen atom of the heterocycle to give the aminotriazoles or iminotriazolines substituted in the ring [1][2][3][4][5][6]. Such an alkylation route is typical of the majority of amino azoles and azines in which the amino group is conjugated with the pyridine type nitrogen atom of the heterocycle [7]. Thus alkylamino-1,2,4-triazoles are usually prepared by cyclization of alkyl substituted acyclic precursors [3, 8-10], hydrogenation of arylideneamino-or acylamino-1,2,4-triazoles [11][12][13], or ammonolysis of halo-substituted 1,2,4-triazoles [4].We have proposed that the alkylation reaction route for the amino-1,2,4-triazoles can be altered by initial acylation or sulfonation of the amino group. In the presence of base an electron acceptor acyl (sulfonyl) group can facilitate deprotonation and give a conjugated N-anion, alkylation of which can give the N-acyl(sulfonyl)-N-alkylamino-1,2,4-triazoles.

show abstract

mentioning

confidence: 64%

Section: Dmsomentioning

confidence: 98%

Section: Dmsomentioning

confidence: 98%

mentioning

confidence: 99%

See 2 more Smart Citations

Alkylation of acyl and sulfonyl derivatives of 3,5-diamino-1-phenyl-1,2,4-triazole

Чернышев

Rakitov

Blinov

et al. 2009

Chem Heterocycl Comp

View full text Add to dashboard Cite

show abstract

“…According to the data of [8,9] the 1 H NMR spectra of 3,5-diamino-1-R-1,2,4-triazoles in DMSO-d 6 have broad discernible singlets for the protons of the 3-NH 2 and 5-NH 2 groups in the region of 5 and 6 ppm respectively. The chemical shifts of 5.08 and 4.75 (3-NH 2 ), 6.15 and 6.05 ppm (5-NH 2 ) correspond to the protons of the amino groups of compounds 1a,b.…”

mentioning

confidence: 98%

Acyl and Sulfonyl Derivatives of 3,5-Diamino-1-R-1,2,4-triazoles

Чернышев

Rakitov

Taranushich

et al. 2005

Chem Heterocycl Compd

View full text Add to dashboard Cite

Depending on the reaction conditions, acylation of unsubstituted 3,5-diamino-1,2,4-triazole leads to the formation of acylation products at both the ring N (1) atom and at the exocyclic amino groups [1][2][3][4]. The direction of acylation of 3,5-diamino-1-R-1,2,4-triazole 1 has not been established precisely up to the present time. It has been shown that brief heating of 3,5-diamino-1-phenyl-1,2,4-triazole (1a ) with acetic anhydride leads to the formation of a monoacetyl derivative, but refluxing in an excess of anhydride leads to the formation of a diacetyl derivative, the structures of which were not determined [5]. The product of the interaction of 1a with acetoacetic ester was assigned the structure of 1-acetoacetyl-3,5-diimino-2-phenyl-1,2,4-triazole [6], but with cyanates and thiocyanates the carbamoyl and thiocarbamoyl derivatives at one of the exocyclic amino groups were formed [7]. The problem of the reaction direction remained open.The aim of the present work is the determination of the direction of acylation and sulfonation reactions of 3,5-diamino-1-R-1,2,4-triazoles 1a,b.It was established that the interaction of compounds 1a,b with an equimolar quantity of anhydrides 2a-c, carboxylic acid chlorides 2d-f,i, and sulfonyl chlorides 2g,h proceeds regioselectively and gives 3-acylamino-5-amino-1-R-1,2,4-triazoles 3a-f,i,j and 5-amino-3-sulfonylamino-1-R-1,2,4-triazoles 3g,h,k in good yield (Scheme 1, Table 1).According to the data of [8,9] the 1 H NMR spectra of 3,5-diamino-1-R-1,2,4-triazoles in DMSO-d 6 have broad discernible singlets for the protons of the 3-NH 2 and 5-NH 2 groups in the region of 5 and 6 ppm respectively. The chemical shifts of 5.08 and 4.75 (3-NH 2 ), 6.15 and 6.05 ppm (5-NH 2 ) correspond to the protons of the amino groups of compounds 1a,b. In the 1 H NMR spectra of compounds 3a-k the 3-NH 2 signal has disappeared, but a signal for an amide proton appears at 9.8-12.5 ppm. The singlet of the 5-NH 2 protons is displaced a little towards low field and appears in the range 6.25-6.60 ppm (Table 2). These values of the __________________________________________________________________________________________ South

show abstract

Design of Inhibitors of Photosystem II using a Model of the D1 Protein

Egner¹,

Gerbling²,

Hoyer³

et al. 1996

Pestic. Sci.

View full text Add to dashboard Cite

Several inhibitors belonging to structurally different chemical classes were used to analyze the predictive power of an initial model of the herbicide binding niche of the D1 protein belonging to photosystem I1 (PS 11) from plants.In the case of small PS I1 inhibitors, the estimation of relative activities was hampered by uncertainty about the binding modes. To overcome this problem, a bulky substituent was introduced into the inhibitors to act as a hook, resulting in an unambiguous orientation in the model. The comparison of the modelling results and the experimentally determined IC,, values of different triazines suggested that the previously assumed volume of the binding niche had to be reduced by 20%. After refinement of the model, it was possible to estimate qualitatively, the relative in-vitro activity for inhibitors belonging to different families, as long as an unambiguous binding mode could be deduced either from steric demands or from IC,, values of mutant DI proteins. The usefulness of the refined model is demonstrated by the successful de-nooo design of a potent class of herbicides, the triazolopyrimidines.

show abstract

On triazoles. V. Synthesis of 1‐ and 2‐R¹‐3‐R²,R³‐amino‐5‐amino‐1,2,4‐triazoles

Cited by 45 publications

References 6 publications

Alkylation of acyl and sulfonyl derivatives of 3,5-diamino-1-phenyl-1,2,4-triazole

Alkylation of acyl and sulfonyl derivatives of 3,5-diamino-1-phenyl-1,2,4-triazole

Acyl and Sulfonyl Derivatives of 3,5-Diamino-1-R-1,2,4-triazoles

Design of Inhibitors of Photosystem II using a Model of the D1 Protein

Contact Info

Product

Resources

About