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1 -Methyl-3- -1,2,4-triazole

Since HF calculations have a tendency to underestimate the N—N and the C—N bond lengths in triazoles [98JPC(A)620, 98JPC(A) 10348], the structural parameters should be computed at least at the DFT or MP2 levels. This is particularly true if electron-donating substituents are attached to the ring. Nitrogen NMR shielding tensors were computed for a set of methylated triazoles and tetrazoles but will be discussed in the context of tetrazoles (cf. Section IV,B). [Pg.28]

The nitrogen NMR shieldings in methylated triazoles and tetrazoles were computed at the GIAO/HF/6-31-I--I-G level and more recently using multireference... [Pg.31]

Acyl hydrazides are useful precursors for the synthesis of 1,2,4-triazoles. Reaction of acyl hydrazides 149 with imidoylbenzotriazoles 148 in the presence of catalytic amounts of acetic acid under microwave irradiation afforded 3,4,5-trisubstituted triazoles 150 <06JOC9051>. Treatment of A-substituted acetamides with oxalyl chloride generated imidoyl chlorides, which reacted readily with aryl hydrazides to give 3-aryl-5-methyl-4-substituted[ 1,2,4]triazoles <06SC2217>. 5-Methyl triazoles could be further functionalized through a-lithiation and subsequent reaction with electrophiles. ( )-A -(Ethoxymethylene)hydrazinecarboxylic acid methyl ester 152 was applied to the one-pot synthesis of 4-substituted-2,4-dihydro-3//-1,2,4-triazolin-3-ones 153 from readily available primary alkyl and aryl amines 151 <06TL6743>. An efficient synthesis of substituted 1,2,4-triazoles involved condensation of benzoylhydrazides with thioamides under microwave irradiation <06JCR293>. [Pg.231]

Photolysis of 2-methyh5-phenyltetrazole gives 4,5-diphenyl-2-methyl-triazole. This may also be formed through a nitrilimine intermediate, although the mechanism has not been established. ... [Pg.62]

Theoretical calculations for the dipole moment of the 1H- (la) and 4H-tautomers (lb) gave values for the IH-tautomer that were closely in agreement with the observed value of triazole, whereas the calculated values for the 4H-tautomer were much higher. Ab initio calculations made at the 6.3IG level gave a good agreement with the observed dipole moment of 2.7ID for 3,5 bis(trifluoro-methyl)triazole (see Section 4.02.4.5). [Pg.130]

Two alternative routes lead to 2-alkyltriazole 1-oxides from a-dicarbonyl compounds (Scheme 50, routes A and B). Unsymmetrical dicarbonyl compounds frequently, but not invariably, give rise to two isomeric hydrazones and two isomeric oximes and hence two isomeric 1,2,3-triazole 1-oxides (81JCS(P1)503). 2-Phenyltriazole 1-oxide is obtained from glyoxal via route A. However, 2-methyl-triazole 1-oxide is prepared from glyoxal by route B in a one-pot process under neutral conditions. 2-Benzyltriazole 1-oxide is obtained similarly. 2,5-Dimethyltriazole 1-oxides are accessible through both routes (86ACS(B)262). [Pg.588]

Partial desilylation of BSMA derivatives has been reported to occur in low yields as the result of a side reaction either during their preparation or their reaction, for example, formation of trimethylsilyl-methyltriazole during the preparation of [bis(trimethylsilyl)-methyl triazole.71 It was conjectured that this could be the result of a nucleophilic attack on the disilyl compound. [Pg.242]

The preparation and reactions of the azine, phenylhydrazone, and phenyl-semicarbazone of 4-amino-5-formyl-2-methyltriazole proceeded normally. One acetal has been prepared as follows. 4-Amino-3-benzyl-5-formyltriazole and boron trifluoride (as diethyl ether complex), stirred in methanol, gave 4-amino-3-benzyl-5-dimethoxymethyltriazole (20°C, 6 hr, 53%) and a dimeric by-product, 4-amino-3-benzyl-5-(3-benzyl-5-dimethoxytriazol-4-ylimino-methyl)triazole [73JCS(P1)2037]. The amino group in 4-aminotriazole-5-carbaldehydes lends itself readily to the formation of amidines and imidates (Section III,B,1), but it resists acylation. [Pg.163]

C. Simons (2001). l-[(Benzofuran-2-yl)phenyl-methyl]triazoles as steroidogenic inhibitors Synthesis and in vitro inhibition of human placental CYP19 aromatase. Anticancer Drug Des. 16, 217-225. [Pg.320]

Cyclocondensation of aryl azides 4 with ethyl acetoacetate 5 in the presence of sodium ethoxide has been reported to lead to the corresponding l-aryl-4-carboxy-5-methyl triazoles 6 with moderate to good yields (Scheme 2) [25]. [Pg.188]

Aiylation of monosubstituted triazole 121 delivers 1,5-disubstituted compound as major product, with a small amount of diaiylated triazole 123. This regioselectivity is correlated by the DPT calculaticHi of electrostatic potential charges at C-4 and C-5 of N-methyl triazole 124 (Scheme 40). [Pg.210]

The 3-amino group brings a second nucleophilic center in these structures thus 2-imino-3-amino-4-methyl-4-thia201ine (409) reacts with methyl diloroformate to give the bicyclic compound (410) (Scheme 234). Other thiazolo-s-triazoles of the [3.2-l>] type have been obtained by... [Pg.130]

C2N3 N N N — — l,3-Dimethyl-4-(l,2,3-triazolyl) sulfide 3-methyl-2-phenyl-l,2,3-triazol-l-ine-4-thione... [Pg.9]

For the NH azoles (Table 3), the two tautomeric forms are usually rapidly equilibrating on the NMR timescale (except for triazole in HMPT). The iV-methyl azoles (Table 4) are fixed chemical shifts are shifted downfield by adjacent nitrogen atoms, but more by a pyridine-like nitrogen than by a pyrrole-like iV-methyl group. [Pg.13]

Ring substituents can have a considerable effect on the acidity of the system. In the 1,2,4-triazole series a 3-amino group decreases the acidity to 11.1, a 3-methyl group to 10.7, whereas a 3-phenyl group Increases the acidity to 9.6, and 3,5-dlchloro substitution to 5.2 (71PMH(3)1). [Pg.51]

Despite the weak basicity of isoxazoles, complexes of the parent methyl and phenyl derivatives with numerous metal ions such as copper, zinc, cobalt, etc. have been described (79AHC(25) 147). Many transition metal cations form complexes with Imidazoles the coordination number is four to six (70AHC(12)103). The chemistry of pyrazole complexes has been especially well studied and coordination compounds are known with thlazoles and 1,2,4-triazoles. Tetrazole anions also form good ligands for heavy metals (77AHC(21)323). [Pg.51]

For both azole and benzazole rings the introduction of further heteroatoms into the ring affects the ease of quaternization. In series with the same number and orientation of heteroatoms, rate constants increase in the order X = 0requires stronger reagents and conditions methyl fluorosulfonate is sometimes used (78AHC(22)71). The 1-or 2-substituted 1,2,3-triazoles are difficult to alkylate, but methyl fluorosulfonate succeeds (7IACS2087). [Pg.52]

N-Unsubstituted 1,2,3-triazoles are methylated mainly in the 1-position with methyl iodide and silver or thallium salts, but mainly in the 2-position by diazomethane. There is also some steric control. For example, 4-phenyl-l,2,3-triazole with dimethyl sulfate gives the 2-methyl-4-phenyl (38%) and l-methyl-4-phenyl isomers (62%), but none of the more hindered 1-methyl-5-phenyltriazole (74AHC(16)33). JV-Unsubstituted 1,2,4-triazoles are generally alkylated at N-1. [Pg.53]

Halogeno-l-methyl-l,2,3-triazoles undergo substitution reactions with amines, but the 4-halogeno analogs do not. 5-Chloro-l,4-diphenyl-l,2,3-triazole with sodium cyanide in DMSO gives the cyano derivative (63JCS2032). 1-Substituted 3-chloro- and 5-chloro-l,2,4-triazoles both react with amines. [Pg.105]

Phenylisoxazolin-5-one condensed with anthranal to give a tricyclic isoxazolylquinoline (Scheme 72) <78CZ264). 3-Methyl-4-phenylazoisoxazoline-5-thione reacted with ethyl chloroacetate for form an intermediate isoxazolethiol, which on heating generated a 1,2,3-triazole (Scheme 73). [Pg.43]

The 1-azirines obtained from the vapor phase pyrolysis of 4,5-disubstituted 1-phthalimido-1,2,3-triazoles (157) have been found to undergo further thermal reactions (71CC1S18). Those azirines which contain a methyl group in the 2-position of the ring are cleaved to nitriles and phthalimidocarbenes, whereas those azirines which possess a phenyl substituent in the 2-position rearrange to indoles. [Pg.66]

Triazole, rrans-5-bromo-4,5-dihydro-4-methyl-l-(4-nitrophenyl)-... [Pg.75]


See other pages where 1 -Methyl-3- -1,2,4-triazole is mentioned: [Pg.289]    [Pg.42]    [Pg.146]    [Pg.119]    [Pg.269]    [Pg.269]    [Pg.887]    [Pg.289]    [Pg.106]    [Pg.108]    [Pg.74]    [Pg.74]    [Pg.74]    [Pg.74]    [Pg.75]    [Pg.75]    [Pg.75]    [Pg.75]    [Pg.75]   


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1 -Methyl-5-hydroxy-1,2,3-triazole, solution

1,2,3 triazole benzyl methyl ketone

1.2.3- Triazole 2-methyl-4,5-dinitro

1.2.3- Triazole 2-methyl-4-nitro

1.2.3- Triazole 4-methyl-2-phenyl

1.2.4- Triazole 1-methyl-, ring synthesis

2- Substituted 1,2,3-triazoles, alkylation with methyl fluorosulfonate

4- Amino-3-methyl- 5-thione-1,2,4-triazole

Methylated triazoles and tetrazoles

Methylated triazoles and tetrazoles computed nitrogen NMR shieldings

Triazoles methylation

Triazoles methylation

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