7465-48-7

Usage

InChI:InChI=1/C5H8N4/c1-2-4-9-5(3-1)6-7-8-9/h1-4H2

Upstream product

• 274-87-3 tetrazolo[1,5-a]pyridine 
• 21994-41-2 5-azidopentanenitrile 
• 660-88-8 5-aminopentanoic acid 
• 120-92-3 cyclopentanone 

Downstream Products

• 32847-45-3 N-(but-3-en-1-yl)cyanamide 
• 926290-89-3 acetic acid phenyl-(5,6,7,8-tetrahydro-tetrazolo[1,5-a]pyridin-8-yl)-methyl ester 
• 954154-12-2 8-benzylidene-5,6,7,8-tetrahydro-tetrazolo[1,5-a]pyridine 

Relevant academic research and scientific papers

Remodeling and Enhancing Schmidt Reaction Pathways in Hexafluoroisopropanol

The effect of carrying out two variations of the Schmidt reaction with ketone electrophiles in hexafluoroisopropanol (HFIP) solvent has been studied. When TMSN3 is reacted with ketones in the presence of triflic acid (TfOH) promoter, tetrazoles are obtained as the major products. This observation is in contrast to established methods, which usually lead to amides or lactams arising from formal NH insertion as the major products. The full product profiles of several examples of this reaction are also reported and found to include mechanistically interesting products (e.g., double ring expansion). Application of TfOH promoter in HFIP was also found to promote the reaction of a hydroxyalkyl azide with a ketone, which affords lactams following nucleophilic opening of initially formed iminium ether more efficiently than previously reported methods. (Chemical Equation Presented).

Convergent Three-Component Tetrazole Synthesis

A microwave-accelerated, simple, and efficient method for the construction of the 1,5-tetrazole scaffold was developed. It comprises a multicomponent reaction of an amine, a carboxylic acid derivative, and an azide source. On the basis of the availability of the archetypical starting materials, this method provided very versatile synthetic access to 1,5-disubstituted tetrazoles. The usefulness of this method was demonstrated in the synthesis of biologically important fused tetrazole scaffolds and the marketed drug cilostazol.

Proximity-assisted cycloaddition reactions - Facile Lewis acid-mediated synthesis of diversely functionalized bicyclic tetrazoles

(Chemical Equation Presented) Aliphatic azidonitriles separated by three or four carbon atoms undergo facile Lewis acid-induced cycloadditions to give bicyclic tetrazoles, even at 0 °C. Extension to 3-azido-2-aryl-1,3- dioxolanes and the corresponding 1,3-dioxanes in the presence of TMSCN and BF3·OEt2 leads to a series of diversely functionalized novel oxabicyclic tetrazoles. The reactions represent new aspects of proximity-assisted dipolar cycloadditions that afford thermodynamically controlled enantiopure products proceeding through discrete oxocarbenium ion intermediates.

Preparation of 1,5-fused tetrazoles under solvent-free conditions

A facile and efficient procedure is developed for a one-pot synthesis of fused 1,5-disubstituted tetrazoles from cyclic ketones and sodium azide in the presence of aluminum chloride in solvent-free media. Advantages of this method are chemoselectivity, with high yields in a simple operation, and short reaction time under solvent-free conditions. Copyright Taylor & Francis, Inc.

Improved Schmidt synthesis of 1,5-disubstituted 1H-tetrazoles from ketones

On treatment with an excess of sodium azide in the presence of titanium(IV) chloride in boiling acetonitrile, both aliphatic and aromatic ketones are smoothly converted to 1,5-disubstituted 1H-tetrazoles in high yields.

Selective Formation of Alkyl Azides Using Trimethylsilyl Azide and Carbonyl Compounds

Whereas tin(II) chloride, or zinc chloride, catalyzed reaction of trimethylsilyl azide (TMSA) with carbonyl compounds gave gem-diazides 3, a catalytic amount of sodium azide/15-crown-5 promoted an addition reaction of TMSA toward these compounds to give α-siloxy azides 2 exclusively.A stereoelectronic effect was found to be important for these reactions.

ADDITION REACTION OF TRIMETHYLSILYL AZIDE TOWARDS KETONES AND FACILE FORMATION OF TETRAZOLE DERIVATIVES

In the presence of Lewis acid such as SnCl2, the reactions of trimethylsilyl azide with ketones readily gave 1:1- or 1:2-adduct, which reacted with Lewis acid to afford tetrazole.