Synthesis of N,N-Disubstituted 3-Amino-1,2,4-triazoles

Katritzky, Alan R.; Rogovoy, Boris V.; Vvedensky, Vladimir Y.; Kovalenko, Katherine V.; Steel, Peter J.; Марков, В. И.; Forood, Behrouz

doi:10.1055/s-2001-13400

Cited by 33 publications

(21 citation statements)

References 1 publication

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“…Acyl derivatives of benzotriazole-1-carboximidamides 215 [165,166] reacted readily with monosubstituted urea to give 1,3,5-triazin-2-ones 320 in the presence of three equivalents of potassium tert-butoxide (Scheme 120) [217]. In the case of N-phenyl urea, only the substitution of the benzotriazole occurred under the same reaction conditions giving stable intermediates 321.…”

Section: Triazinesmentioning

confidence: 95%

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Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Beagle

2015

Topics in Heterocyclic Chemistry

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Application of benzotriazole methodology for the preparation of nitrogen-containing heterocyclic compounds is summarized in this review. The characteristic advantages of benzotriazole are first briefly considered followed by an overview of its use in the synthesis of heterocycles organized by the ring size. Finally, the use of benzotriazole in the synthesis of bicyclic systems is showcased in only selected examples.

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Section: Triazinesmentioning

confidence: 95%

“…In contrast, phenyl or benzyl hydrazine reacted with acyl derivatives 215 with the competitive formation of 216 and 3-benzotriazole-substituted triazole 217. The lower the electron-donating character of the substituent of the hydrazine, the more of the side product 217 is formed (Scheme 77) [165].…”

Section: Triazolesmentioning

confidence: 99%

Benzotriazole-Mediated Synthesis of Nitrogen-Containing Heterocycles

Beagle

2015

Topics in Heterocyclic Chemistry

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“…8 Only a few methods have been developed for the synthesis of 1,5-disubsituted 3-amino-1H-triazoles in the literature. 2,[9][10][11] For example, the reaction of (benzotriazolyl)methanimines and substituted hydrazines readily generates N,N-disubstituted 3-amino-1H-1,2,4-triazoles; 9,10 however, this chemistry is unable to produce N,N-unsubstituted triazole compounds (Scheme 1, A). Condensation of resin-bound S-methyl-N-acylisothioureas with hydrazines led to the desired 1,5-disubstituted 3-aminotriazles after acid-promoted resin cleavage (Scheme 1, B).…”

mentioning

confidence: 98%

A Safe Synthesis of 1,5-Disubstituted 3-Amino-1H-1,2,4-triazoles from 1,3,4-Oxadiazolium Hexafluorophosphates

Wong¹,

Stumpf²,

Carrera³

et al. 2013

Synthesis

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Hexafluorophosphoric acid promotes 1,3,4-oxadiazolium hexafluorophosphate formation from N′-acyl-N-aroyl-N-arylhydrazides or N′-acyl-N-acyl-N-arylhydrazides under mild conditions. These 1,3,4-oxadiazolium hexafluorophosphates can be treated with cyanamide in propan-2-ol in the presence of triethylamine to generate 1,5-disubstituted 3-amino-1H-1,2,4-triazoles in good yields. This safe and scalable protocol displays a broad scope with respect to N-substitutions and N′-acyl protecting groups.

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“…1 H NMR and HPLC of products demonstrated the presence of a single isomer and the cyclization are regioselective as previously reported. 6c, 11 It is expected that the lower yield found was due to substitution of the methyl thio group by hydrazine, followed by cyclization and concomitant cleavage upon reaction of the hydrazino group with the urethane carbonyl. Figure 1 illustrates a typical LC-MS spectrum of crude product of 5b.…”

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confidence: 99%