160290-40-4

Upstream product

• 61-82-5 3-amino-1,2,4-triazole 
• 61-82-5 3⁽⁵⁾-amino-1,2,4-triazole 
• 1122-91-4 4-bromo-benzaldehyde 
• 121-44-8 triethylamine 
• 73387-60-7 1-(4-bromophenyl)-3-(dimethylamino)prop-2-en-1-one 

Relevant academic research and scientific papers

Vinylation of α-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-a]pyrimidines with a Nonsubstituted Ethylidene Fragment

A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon.

Synthesis method of [1, 2, 4] triazolo [1, 5-a] pyrimidine compound

The invention discloses a synthesis method of a [1, 2, 4] triazolo [1, 5-a] pyrimidine compound, and belongs to the technical field of organic synthesis. According to the technical scheme, the preparation method is characterized by comprising the following steps: dissolving an aldehyde compound, a 3-amino-1, 2, 4-triazole compound and triethylamine in a solvent toluene, then adding ammonium iodide and di-tert-butyl peroxide, and then reacting at 130 DEG C to prepare the target product [1, 2, 4] triazole [1, 5-a] pyrimidine compound. The synthesis process is simple and efficient, the [1, 2, 4] triazolo [1, 5-a] pyrimidine compound is directly prepared in one step through the one-pot cascade reaction without transition metal catalysis, the synthesis process is convenient to operate, the raw materials are simple, the reaction conditions are mild, the yield is high, the method has a very good application prospect, and meanwhile, the production cost is greatly reduced by taking triethylamine as the raw material.

Ultrasound irradiation promotes the synthesis of new 1,2,4-triazolo[1,5-a] pyrimidine

Ultrasonic irradiation was used in the synthesis of a series of novel 1,2,4-triazolo[1,5-a]pyrimidines. The products were synthetized from the cyclocondensation reaction of 1,1,1-trifluoro-4-metoxy-3-alken-2-one [CF 3C(O)CHC(R)OMe, where R = Ph, 4-F-C6H4, 4-Br-C6H4, 4-I-C6H4, 4-CH 3-C6H4, 4-CH3O-C6H 4, Thien-2-yl, Biphen-4-yl] or β-enaminones [RC(O)CHCHNMe 2, where R = Ph, 4-F-C6H4, 4-Br-C 6H4, 4-I-C6H4, 4-CH 3-C6H4, 4-CH3O-C6H 4, 4-NO2-C6H4, Thien-2-yl, Biphen-4-yl, Naphth-2-yl, Pyrrol-2-yl, CCl3] with 5-amino-1,2,4-triazole in acetic acid at 99 C with 5-17 min of ultrasound irradiation. This methodology has shown several advantages, such as shorter reaction times, mild conditions, high regioselectivity, and excellent yields, when compared with conventional thermal heating (oil bath).

The application of unsymmetrical vinylogous iminium salts and related synthons to the preparation of monosubstituted triazolo[1,5-a]pyrimidines

The reaction of vinylogous iminium salts and related analogs with 3-amino-1,2,4-triazole to yield 7-substituted and 5-substituted triazolo[1,5-a]pyrimidines is described.