7477-13-6

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
Tetrazolo[1,5-a]pyridine-6-carboxylic acid is utilized as a key intermediate in the development of pharmaceuticals and agrochemicals due to its inherent biological activity and potential therapeutic benefits. Its unique structure and reactivity contribute to the creation of new compounds with a range of applications in these fields.
Used in Antiviral, Antibacterial, and Antifungal Applications:
In the medical and healthcare industry, Tetrazolo[1,5-a]pyridine-6-carboxylic acid is employed as an antiviral, antibacterial, and antifungal agent. Its potential in these areas is attributed to its ability to target and inhibit the growth of various pathogens, thereby offering therapeutic solutions for a range of infectious diseases.
Used in Material Science and Organic Synthesis:
Tetrazolo[1,5-a]pyridine-6-carboxylic acid also finds applications in material science and organic synthesis. Its versatile reactivity and unique structural features make it an ideal building block for the development of new compounds with diverse properties, contributing to advancements in various material and chemical applications.

InChI:InChI=1/C6H4N4O2/c11-6(12)4-1-2-5-7-8-9-10(5)3-4/h1-3H,(H,11,12)

Upstream product

• 351324-62-4 6-azidopyridine-3-carboxylic acid 
• 6311-35-9 6-bromonicotinic acid 
• 3510-66-5 2-Bromo-5-methylpyridine 

Relevant academic research and scientific papers

Dual Reactivity of 1,2,3,4-Tetrazole: Manganese-Catalyzed Click Reaction and Denitrogenative Annulation

A general catalytic method using a Mn-porphyrin-based catalytic system is reported that enables two different reactions (click reaction and denitrogenative annulation) and affords two different classes of nitrogen heterocycles, 1,5-disubstituted 1,2,3-triazoles (with a pyridyl motif) and 1,2,4-triazolo-pyridines. Mechanistic investigations suggest that although the click reaction likely proceeds through an ionic mechanism, which is different from the traditional click reaction, the denitrogenative annulation reaction likely proceeds via an electrophilic metallonitrene intermediate rather than a metalloradical intermediate. Collectively, this method is highly efficient and offers several advantages over other methods. For example, this method excludes a multi-step synthesis of the N-heterocyclic molecules described and produces only environmentally benign N2 gas a by-product.

Iron(II)-Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation

A unique concept for the intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by using a catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.

NMR studies of the equilibria produced by 6- and 8-substituted tetrazolo [1,5-a] pyridines

1H, 13C and 15N NMR data are reported for nine tetrazoles. Five of these compounds are found to exhibit valence tautomeric equilibrium between the tetrazole and azide forms. The position of this equilibrium at 298 K is found to be dependent on the solvent and the position and nature of the substituent. More polar solvents favour the tetrazole form. Protonation studies on the two forms using TFA as a solvent are reported. The favoured site of protonation is found to be N-4 for the azide form and N-1 for the tetrazole form.