61795-72-0

Usage

Chemical class

Tetrazoles

Stability

Unstable and highly reactive

Occurrence

Not commonly found in nature

Uses

Building block or intermediate in the synthesis of pharmaceuticals and agrochemicals

Properties

Useful precursor for the synthesis of biologically active compounds

Applications

Development of new drugs and pesticides

Upstream product

• 75-36-5 acetyl chloride 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 320603-09-6 1-Methyl-5-p-tolyloxy-1H-tetrazole 
• 13183-79-4 1-methyl-1,4-dihydro-tetrazole-5-thione 
• 16681-79-1 5-bromo-1-methyl-1H-tetrazole 
• 5422-44-6 1-methyl-5-amino-1H-tetrazole 

Downstream Products

• 13576-20-0 5-oxo-1,4-dimethyl-1,4-dihydro-5H-tetrazole 
• 1067924-70-2 1-{2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]benzyl}-4-methyl-1,4-dihydro-5H-tetrazol-5-one 
• 1309832-24-3 3-(4,5-dihydro-4-methyl-5-oxotetrazol-1-yl)-5-nitrobenzonitrile 

Relevant academic research and scientific papers

Novel Type Elimination Reactions of Sulfoxides Bearing Several Heteroaromatics: Trapping of Sulfines with 2,3-Dimethyl-1,3-butadiene

Previously we reported the novel thioaldehydes generation via thermolyses of phenacyl sulfoxides bearing some heteroaromatics. Thermolysis of sulfoxides (1a,b and 2a-4a) bearing other heterocycles such as thiadiazole, triazole, and tetrazole in the presence of 2,3-dimethyl-1,3-butadiene in dioxane at 100 °C led to the unexpected products 6-substituted-5,6-dihydro-3,4-dimethyl-2H-thiapyran 1-oxide (5a,b). These products were considered to be formed by the Diels-Alder reaction of the diene with the sulfines formed initially by the thermal decomposition of the sulfoxides. The rate acceleration and the improvement of the yield by addition of 1.5 equiv of triethylamine, especially in the case of ethoxycabonylmethyl sulfoxide 1c, was observed. The cis-trans selectivity for sulfine cycloadducts was also studied by NMR spectrometry. The reactions of α-substituted phenacyl sulfoxides 1d-f bearing a phenyl-substituted tetrazolyl group in the presence of the same diene were also studied.

Process for the preparation of 1-4-disubstituted-5 (4H)-tetrazolinones

1,4-Disubstituted-5(4H)-tetrazolinones of the formula (I) STR1 wherein R1, R2 and R3 have the meanings given in the specification), which are known to be useful as herbicides, can be obtained in very good yields by reacting the corresponding 1-substituted-5(4H)-tetrazolinones with the corresponding carbamoyl chlorides in the presence of 4-dimethylaminopyridine.

Process for the preparation of 1-substituted-5(4H)-tetrazolinones

A process for the preparation of a 1-substituted-5(4H)-tetrazolinone of the formula STR1 wherein R1 is defined in the specification n is 0, 1, 2, 3 or 4, which comprises reacting a 1-substituted-5(4H)-tetrazolinethione of the formula STR2 with an ethylene oxide of the formula STR3 wherein R2 represents hydrogen, methyl or ethyl, in the presence of a base and in the presence of water, an alcohol or a mixture thereof.

METAL-ASSISTED REACTIONS-13. RAPID, SELECTIVE REDUCTIVE CLEAVAGE OF PHENOLIC HYDROXYL GROUPS BY CATALYTIC TRANSFER METHODS

Previous work has shown that, after converting phenols into suitable phenolic ethers, the aromatic C-O bond of the original phenol can be reductively cleaved heterogeneously to give a C-H bond through the use of molecular hydrogen or hydrogen donors together with a transition metal catalyst.The present work provides a method for selectively replacing a phenolic OH group by H in just a few minutes, compared with the 2 to 4 hr required previously using a hydrogen donor and the several hours under pressure required for molecular hydrogen.Various kinds of groups are suitable for preparing the required phenolic ethers from phenols, but the best ones are strongly electronwithdrawing heteroaromatic entities.Solvent appears to play an important role in this heterogeneous reaction, the mechanism of which is discussed.