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Usage

Uses

Used in Organic Chemistry:
7-Chloro-tetrazolo[1,5-a]pyridine is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows for the formation of diverse chemical entities, making it a valuable building block in the synthesis of complex molecules.
Used in Medicinal Chemistry:
7-Chloro-tetrazolo[1,5-a]pyridine is used as a key component in the development of new pharmaceuticals. Its potential biological activity and structural properties make it a promising candidate for the creation of novel drug molecules, particularly in the context of medicinal applications.
Used in Drug Design:
7-Chloro-tetrazolo[1,5-a]pyridine is used as a molecular scaffold in the design of new drugs. Its presence in the molecular structure can influence the pharmacological properties of the resulting compounds, such as their potency, selectivity, and bioavailability, ultimately contributing to the development of more effective therapeutic agents.
Used in Research and Development:
7-Chloro-tetrazolo[1,5-a]pyridine is used as a research tool in the exploration of new chemical reactions and mechanisms. Its reactivity and structural features make it an ideal candidate for studying the fundamental principles of organic and medicinal chemistry, furthering our understanding of chemical processes and their applications in drug discovery.

Upstream product

• 16110-09-1 2,5 dichloropyridine 
• 4214-79-3 5-chloro-2-pyridinol 
• 1851-22-5 3-chloropyridine-N-oxide 

Downstream Products

• 1606181-83-2 6-chloro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine 

Relevant academic research and scientific papers

One-step conversion of pyridine N-oxides to tetrazolo[1,5-a]pyridines

(Chemical Equation Presented) Pyridine N-oxides were converted to tetrazolo[1,5-a]pyridines in good to excellent yield by heating in the presence sulfonyl or phosphoryl azides and pyridine in the absence of solvent. Various sulfonyl and phosphoryl azides were screened for reactivity under a standard set of conditions. Diphenyl phosphorazidate was the most convenient reagent and gave high yields. Reaction optimization, scope, and scalability are discussed.

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.

SNAr azidation of phenolic functions utilizing diphenyl phosphorazidate

A useful method for the synthesis of aryl azides via SNAr reaction of phenol derivatives using diphenyl phosphorazidate (DPPA) as an azidation reagent was developed. Various phenol derivatives bearing electron-withdrawing groups were converted into the corresponding aryl azides in a single step. This method is easy to perform and enables the preparation of aryl azides without the use of explosive azide sources.

1H, 13C and 15N NMR and IR studies of halogen-substituted tetrazolo[1,5-a]pyridines

The tetrazole-azide tautomerization of some halogen-substituted tetrazolo[1,5-a]pyridines was examined by IR spectroscopy at ambient temperature and by 1H, 13C and 15N NMR spectroscopy at various temperatures. The tetrazolopyridines can exhibit equilibrium between the azide and the tetrazole forms. For some of them slow exchange occurs on the NMR time-scale, such that it is possible to estimate equilibrium constants. The position and nature of the substituent in the pyridine ring result in stabilization or destabilization of the tetrazole form and exert a strong influence on the values found for the equilibrium constants. A saturation transfer experiment was carried out for 5-bromotetrazolo[1,5-a]pyridine and the rate constants were estimated. Moreover, based on the van't Hoff equation, the enthalpy ΔHo and entropy ΔSo for the tautomerization were calculated. Ab initio calculated energies and charge distribution are in good agreement with differences observed in the tetrazole-azide equilibrium constants. Copyright