New methods for the synthesis of substituted 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazines (microreview)

Tupychak, M.; Обушак, Н. Д.

doi:10.1007/s10593-021-03037-8

Cited by 2 publications

(16 citation statements)

References 19 publications

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“…The dipolarophilic group for the Huisgen-1,3-dipolar cycloaddition to construct the [1,2,3]triazolo [1,5-a]pyrazin-6(7H)-one system could also be involved in the Ugi reaction via the aldehyde moiety. First, 3-phenylpropiolaldehyde was tested in the Ugi reaction with 2-azido-3-arylpropionic acids.…”

Section: Paper Synthesismentioning

confidence: 99%

“…In addition, compounds of this class were found to possess antitumor activity. 9 Therefore, the development of suitable methods to obtain 4,5,6,7-tetrahydro [1,2,3]triazolo [1,5a]pyrazines is an important area of research. [1,2,3]triazolo [1,5-a]…”

Section: -98%mentioning

confidence: 99%

“…A general approach to the simultaneous formation of 1,2,3-triazole and pyrazine rings is the 1,3-dipolar cyclization of -azido-N-(prop-2-ynyl)amides. A previously described two-step approach to obtain [1,2,3]triazolo [1,5a]pyrazines proceeded via a sequential Ugi reaction involving an -azidoacetic acid or an -azidophenylacetic acid and propargylamine, followed by a Huisgen cyclization In the present work, we have developed a convenient method for the synthesis of 2-azido-3-arylpropanoic acids based on the Meerwein arylation and have utilized the obtained adducts in a tandem Ugi-Huisgen sequence for the synthesis of new 4,5,6,7-tetrahydro [1,2,3]triazolo [1,5a]pyrazines.…”

Section: Pyrazinesmentioning

confidence: 99%

“…13 C NMR (126 MHz, DMSO-d 6 ):  = 166.33 (CON), 165.03 (CON), 161.93 (d,1 J C-F = 244.2 Hz, C Ar -3), 155.61, 137.10 (d,3 J C-F = 8.0 Hz, C Ar -1), 133.65, 132.97, 131.72, 131.05, 130.80, 130.05 (d, 3 J C-F = 8.3 Hz, CH Ar -5), 129.17, 128.88, 128.42, 125.34 (d, 4 J C-F = 2.4 Hz, C Ar -6), 124.99, 120.79 (2 C), 116.25 (d, 2 J C-F = 21.1 Hz, CH Ar -4), 114.00 (2 C), 113.92 (d, 2 J C-F = 20.9 Hz, CH Ar -2), 61.56, 59.81, 55.23, 38.71, 38.09. MS (APCI): m/z = 564, 566 [M + H] + .…”

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The Synthesis of Novel 7-(Substituted benzyl)-4,5-dihydro[1,2,3]triazolo[1,5-a]pyrazin-6(7H)-ones via Tandem Ugi–Huisgen Reactions

et al. 2022

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A convenient method for the synthesis of 2-azido-3-arylpropanoic acids via the Meerwein halogenoarylation reaction of acrylic acid esters with diazonium salts, subsequent nucleophilic substitution of the halogen by an azide, and saponification is developed. The newly formed 2-azido-3-arylpropanoic acids react under the conditions of non-catalytic four-component Ugi reactions, leading to the formation of α-azidoamides in good yields. The use of propargylamine as the amine component allows the formation of Ugi adducts with azide and acetylene motifs ready for intramolecular 1,3-dipolar Huisgen cycloaddition to give the [1,2,3]triazolo[1,5-a]pyrazine annulated system. The Ugi reaction is found to give 2-azido-3-aryl-N-(2-oxo-1,2-disubstituted ethyl)-N-(prop-2-yn-1-yl)propanamides at room temperature without azide–alkyne cycloaddition. These dipeptides are converted into 4,5-dihydro[1,2,3]triazolo[1,5-a]pyrazin-6(7H)-ones in near quantitative yields by heating in toluene. However, when the Ugi reaction is carried out by heating, it results in a one-pot Ugi–Huisgen tandem reaction leading to 4,5-dihydro[1,2,3]triazolo[1,5-a]pyrazin-6(7H)-ones in excellent yields. Moreover, the possibility of the incorporation of a bromovinyl fragment (the synthetic equivalent of an acetylene fragment) via the aldehyde component of the Ugi reaction is demonstrated in an alternative preparation of the [1,2,3]triazolo[1,5-a]pyrazine system.

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Section: Paper Synthesismentioning

confidence: 99%

Section: -98%mentioning

confidence: 99%

Section: Pyrazinesmentioning

confidence: 99%

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The Synthesis of Novel 7-(Substituted benzyl)-4,5-dihydro[1,2,3]triazolo[1,5-a]pyrazin-6(7H)-ones via Tandem Ugi–Huisgen Reactions

et al. 2022

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“…Therefore, this section is organized into the syntheses of benzo-fused structures (e.g., 1,2,3-triazolo[1,5- a ]pyrazines containing quinoxaline or quinoxalinone), and those that are bicyclic 1,2,3-triazolo[1,5- a ]pyrazines. A recent brief review of 4,5,6,7-tetrahydro[ 1 , 2 , 3 ]triazolo[1,5- a ]pyrazines has been published [ 31 ]. An earlier review detailed aspects of the chemistry of 1,2,3-triazolo[1,5- a ]pyrazines [ 32 ].…”

Section: Synthetic Approachesmentioning

confidence: 99%

Syntheses and Applications of 1,2,3-Triazole-Fused Pyrazines and Pyridazines

Hoffman

Schoffstall

2022

Molecules

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Pyrazines and pyridazines fused to 1,2,3-triazoles comprise a set of heterocycles obtained through a variety of synthetic routes. Two typical modes of constructing these heterocyclic ring systems are cyclizing a heterocyclic diamine with a nitrite or reacting hydrazine hydrate with dicarbonyl 1,2,3-triazoles. Several unique methods are known, particularly for the synthesis of 1,2,3-triazolo[1,5-a]pyrazines and their benzo-fused quinoxaline and quinoxalinone-containing analogs. Recent applications detail the use of these heterocycles in medicinal chemistry (c-Met inhibition or GABAA modulating activity) as fluorescent probes and as structural units of polymers.

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New methods for the synthesis of substituted 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazines (microreview)

Cited by 2 publications

References 19 publications

The Synthesis of Novel 7-(Substituted benzyl)-4,5-dihydro[1,2,3]triazolo[1,5-a]pyrazin-6(7H)-ones via Tandem Ugi–Huisgen Reactions

The Synthesis of Novel 7-(Substituted benzyl)-4,5-dihydro[1,2,3]triazolo[1,5-a]pyrazin-6(7H)-ones via Tandem Ugi–Huisgen Reactions

Syntheses and Applications of 1,2,3-Triazole-Fused Pyrazines and Pyridazines

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