40060-76-2

Upstream product

• 532-28-5 (RS)-mandelonitrile 
• 127843-38-3 4-Tetrazol-2-ylmethyl-morpholine 
• 100-52-7 benzaldehyde 
• 208122-80-9 (1-Benzyloxymethyl-1H-tetrazol-5-yl)-phenyl-methanol 
• 164589-82-6 1-(1-benzyl-1H-tetrazol-5-yl)(phenyl)methanol 
• 119718-87-5 cyano(phenyl)methyl acetate 

Downstream Products

• 18489-25-3 5-benzyl-1H-tetrazole 
• 43134-03-8 diphenyl(1H-tetrazol-5-yl)methanol 
• 132778-86-0 1,2-diphenyl-1,2-bis-(1H-tetrazol-5-yl)-ethane-1,2-diol 
• 14506-41-3 phenyl(1H-tetrazol-5-yl)methanone 

Relevant academic research and scientific papers

N-Morpholinomethyl-5-lithiotetrazole: A Reagent for the One-Pot Synthesis of 5-(1-Hydroxyalkyl)tetrazoles

An efficient, one-pot method for the preparation of 5-(1-hydroxyalkyl)tetrazoles is reported. N-Morpholinomethyl-5-lithiotetrazole, generated by the deprotonation of 4-(N-tetrazolylmethyl)morpholine with LiHMDS, undergoes addition to ketones and aldehydes (both aromatic and aliphatic) to form 5-(1-hydroxyalkyl)tetrazoles in a high yield, after acidic workup. The reported protocol displays a broad substrate scope and functional group tolerance, avoids the use of cyanide- or azide-based reagents, and provides access to sterically congested and unsaturated tetrazoles, which are difficult to access by other means.

Antibacterial assessment of heteroaryl, Vinyl, Benzyl, and Alkyl tetrazole compounds

Background: In previous reports, the antibacterial properties of certain tetrazole derivatives have been described. We have previously reported the antibacterial properties of aryl 1H-tetrazole compounds. Objective: To study the antibacterial activity of 5-substituted heteroaryl, vinyl, benzyl, and alkyl 1H-tetrazole derivatives. Methods: The antibacterial properties of heteroaryl, vinyl, benzylic, and aliphatic tetrazole derivatives were investigated against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. The activity was assessed by determining the minimum inhibitory concentration of these tetrazole derivatives and comparing them to the known antibiotics amoxicillin, trimethoprim and sulfamethoxazole. Results: The tetrazole compounds were prepared utilizing cerium(III) chloride heptahydrate catalysis at 160o C for 1-4 h in a microwave reactor using an aqueous solvent mixture. The most active derivatives exhibited minimum inhibitory concentration values between 125-250 μg/mL against Escherichia coli. More importantly, these compounds were considerably more active when used in combination with trimethoprim and a significant synergistic effect was observed (MIC = 0.98-7.81 μg/mL) against E. coli and S. aureus. Conclusion: The tetrazole derivatives were synthesized in high yield and short reaction times in water. Several of the tetrazole compounds showed a significant synergistic antibacterial effect when used with trimethoprim.

Microwave Synthesis of 5-Substituted 1 H-Tetrazoles Catalyzed by Bismuth Chloride in Water

(Chemical Equation Presented). Bismuth chloride was used to catalyze the [2 + 3] cycloaddition between sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles. A number of 5-substituted 1H-tetrazoles were synthesized in water or isopropano

1,3-Dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles

Cheap and safe: Conventional methods to prepare tetrazoles employ dangerous, toxic reagents. A new route to these heterocycles (see scheme) uses inexpensive and nontoxic dialkyl aluminum azides. The cycloaddition occurs under mild conditions and tolerates a variety of functional groups. The low cost and ecocompatibility make this process attractive for large-scale preparation. (Chemical Equation Presented).

Homologation of 1-(benzyloxymethyl)-1H-tetrazole via lithiation

Lithiation of 1-(Benzyloxymethyl)-1H-tetrazoIe, prepared by alkylation of 1H-tetrazole with benzyl chloromethyl ether, followed by treatement with a variety of electrophiles afforded its homologation products. Hydrogenation or acid hydrolysis gave the corresponding free tetrazoles.

Application of of 5-Lithiotetrazoles in Organic Synthesis

Lithiation of 1-benzyl and 1-p-methoxybenzyltetrazole at the 5-position with n-butyllithium followed by treatment with electrophiles gave functionalized 1-benzylic tetrazoles, which were converted into the 1-unsubstituted derivatives by debenzylation.