Unexpected alternative direction of a Biginelli-like multicomponent reaction with 3-amino-1,2,4-triazole as the urea component

Gorobets, Nikolay Yu.; Sedash, Yuriy V.; Ostras, Konstantin S.; Zaremba, Oleg V.; Shishkina, S. V.; Baumer, V. N.; Шишкин, Олег В.; Kovalenko, Sergiy M.; Десенко, С. М.; Eycken, Erik V. Van der

doi:10.1016/j.tetlet.2010.02.045

Cited by 55 publications

(37 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…If the reaction was performed at 40 °C in methanol, the diol product 246 would be obtained as main product in 60% yield. The structures confirmed by single crystal X-ray diffraction clearly showed that the condensation of 3-amino 1,2,4-triazole with aldehyde occurred in the exocyclic amino group not on the endocyclic nitrogen of triazole ring (Scheme 106) [308].…”

Section: Modification Of Amino Groupsmentioning

confidence: 93%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

View full text Add to dashboard Cite

Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

show abstract

Section: Modification Of Amino Groupsmentioning

confidence: 93%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

View full text Add to dashboard Cite

show abstract

“…2 Moreover, the introduction of an OHgroup in the ortho-position of an aromatic ring of the aldehyde additionally allows oxygen-bridged and several other types of final structure. 3,4 Multicomponent synthesis of oxygen-bridged pyrimidine systems has been described in several publications. 3e6 In most cases it was realized as three-component condensation of a nitrogencontaining binucleophile (urea and its derivatives, aminoazoles), ortho-salicylaldehyde, and CH-acid (ketones, 1,3-dicarbonyl compounds, b-ketoacids, and their derivatives etc.).…”

Section: Introductionmentioning

confidence: 99%

“…3e6 In most cases it was realized as three-component condensation of a nitrogencontaining binucleophile (urea and its derivatives, aminoazoles), ortho-salicylaldehyde, and CH-acid (ketones, 1,3-dicarbonyl compounds, b-ketoacids, and their derivatives etc.). Such heterocyclizations were carried out both under the classical conventional conditions and with the use of microwave irradiation, 3 as well as with application of different catalysts. 5,6 Application of sequential reactions of nitrogen-containing binucleophiles with preliminary obtained a,b-unsaturated ketones was also described for the synthesis of oxygen-bridged pyrimidine systems.…”

Section: Introductionmentioning

confidence: 99%

Features of switchable multicomponent heterocyclizations of salicylic aldehydes and 5-aminopyrazoles with pyruvic acids and antimicrobial activity of the reaction products

et al. 2013

Self Cite

View full text Add to dashboard Cite

“…[23][24][25][26] For instance, Gorobets et al 23 described a Biginelli-type three-component reaction between 3-amino-1,2,4-triazole, several carbonyl containing CH-acids and aldehydes. They showed that in the case of salicylic aldehyde depending on conditions applied the treatment yielded either 4,5,6,7- 24 in a very similar reaction observed the formation of spiro-compounds instead of bridged heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Behavior of 5-amino-3-methylisoxazole in multicomponent heterocyclizations with carbonyl compounds under thermal heating and non-classical conditions

Muravyova¹,

Тkachenko²,

Десенко³

et al. 2013

Arkivoc

Self Cite

View full text Add to dashboard Cite

Three-component heterocyclizations of 5-amino-3-methylisoxazole, cyclohexanedione derivatives, and aromatic aldehydes, including salicylic aldehydes, are studied under conventional thermal heating, microwave irradiation and ultrasonication. A dependence of the direction of the reaction on the structure of the aldehyde and the reaction conditions was found, which allowed selective synthesis of 6,7,8,9-tetrahydroisoxazolo[5,4-b]quinolin-5(4H)-ones and 2,3,4,9-tetrahydro-1H-xanthen-1-ones. Key stages of the reaction mechanisms are discussed.

show abstract

Unexpected alternative direction of a Biginelli-like multicomponent reaction with 3-amino-1,2,4-triazole as the urea component

Cited by 55 publications

References 20 publications

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Features of switchable multicomponent heterocyclizations of salicylic aldehydes and 5-aminopyrazoles with pyruvic acids and antimicrobial activity of the reaction products

Behavior of 5-amino-3-methylisoxazole in multicomponent heterocyclizations with carbonyl compounds under thermal heating and non-classical conditions

Contact Info

Product

Resources

About