87597-26-0

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMOIMIDAZO[1,2-A]PYRAZINE is used as a key building block for the synthesis of various pharmaceuticals. Its unique structure and reactivity allow for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 5-BROMOIMIDAZO[1,2-A]PYRAZINE serves as a crucial component in the creation of pesticides and other crop protection agents. Its incorporation into these products enhances their effectiveness in managing pests and diseases.
Used in Organic Chemistry Research:
5-BROMOIMIDAZO[1,2-A]PYRAZINE is utilized as an intermediate in the production of a wide range of organic compounds. Its versatility makes it a valuable asset in advancing the field of organic chemistry, facilitating the discovery and synthesis of novel compounds with diverse applications.
Used in Chemical Synthesis Education:
As a model compound, 5-BROMOIMIDAZO[1,2-A]PYRAZINE is employed in educational settings to illustrate the principles of chemical synthesis and the properties of heterocyclic compounds, providing students with hands-on experience in organic chemistry techniques.

InChI:InChI=1/C6H4BrN3/c7-5-3-8-4-6-9-1-2-10(5)6/h1-4H

Upstream product

• 274-79-3 imidazo[1,2-a]pyrazine 

Relevant academic research and scientific papers

Visible-light-promoted oxidative halogenation of (hetero)arenes

Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.

Aryl halide and synthesis method and application thereof

The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

Synthesis of 5-bromo-6-methyl imidazopyrazine, 5-bromo and 5-chloro-6-methyl imidazopyridine using electron density surface maps to guide synthetic strategy

Small heteroaromatic rings are valuable monomers in drug discovery that can enable rapid access to novel and desirable chemical space. Installation of a synthetic handle on a heteroaromatic core may be difficult if steric and electronic factors are not in alignment with the desired transformation. Described are practical routes for the construction of 5-bromo-6-methyl imidazopyrazine (1) as well as 5-bromo and 5-chloro-6-methyl imidazopyridines (2a and 2b), which were developed using electron density surface maps encoded with ionization potential to guide synthetic strategy.

Imidazopyrazine, Bromo and Methoxy Derivatives: a 13C N.M.R. Determination Applied to Nucleophilic Substitution Studies

The 13C chemical shifts and coupling constants of imidazopyrazine and some of its derivatives are reported and compared with those of other series.These data enable us to study the nucleophilic substitution of 3,5-dibromoimidazopyrazine and 6,8-dibromoimidazopyrazine by a methoxy group.

Synthesis of imidazo[1,2-a]pyrazine derivatives with uterine-relaxing, antibronchospastic, and cardiac-stimulating properties

A series of imidazo[1,2-a]pyrazine derivatives was synthesized by condensation of α-halogenocarbonyl compounds and aminopyrazines. Various compounds resulted from competitive reactions or reagent isomerization and demonstrated in vitro uterine-relaxing and in vivo antibronchospastic activities. On isolated atria, 5-bromoimidazo[1,2-a]pyrazine showed positive chronotropic and inotropic properties; the latter was associated with an increase in the cyclic AMP tissue concentration. Potentiation of the isoproterenol positive inotropic effect of 5-bromoimidazo[1,2-a]pyrazine and the lack of blockade of the 5-bromoimidazo[1,2-a]pyrazine positive inotropic effect by propranolol suggested phosphodiesterase-inhibiting properties.