Reactivity of 2-amino-1,3,4-thiadiazoles. Methylation reactions of some 2-amino-5-benzoyl-1,3,4-thiadiazoles

doi:10.1002/JHET.5570120506

Paper

Reactivity of 2-amino-1,3,4-thiadiazoles. Methylation reactions of some 2-amino-5-benzoyl-1,3,4-thiadiazoles

Published 1975 · Giuseppe Werber, Francesco Buccheri, Nicolò Vivona

Journal of Heterocyclic Chemistry

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Abstract

Methylation reactions of 2-amino-5-benzoyl-1,3,4-thiadiazoles 1a-d are reported as a function of alkylating agents (methyl iodide, dimethyl sulfate-potassium carbonate, diazomethane, dimethyl-sulfate-sodium methoxide). Methylation occurs at both the ring nitrogen in position 3 and the exocyclic nitrogen atom.

Study Snapshot

Methylation reactions of 2-amino-5-benzoyl-1,3,4-thiadiazoles 1a-d show potential for synthesis of new compounds with potential applications in organic synthesis and catalysis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Reactivity of 2-amino-1,3,4-thiadiazoles. Methylation reactions of some 2-amino-5-benzoyl-1,3,4-thiadiazoles

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References

Position of methylation of 2,3-diaminopyridine and 3-amino-2-methyl-aminopyridine

Methylation of 2,3-diaminopyridine (V) is solvent-dependent, with steric and hydrogen-bonding effects influencing the position of methylation.

Citations

Synthesis of Novel 2‐Amino‐(2‐thioxo‐3‐alkyl‐4‐methyl‐3H‐thiazol‐5‐yl)‐[1,3,4]thiadiazole Derivatives and Their Growth Stimulant Activity

Novel 2-amino-(2-thioxo-3-alkyl-4-methyl-3H-thiazol-5-yl)-[1,3,4]thiadiazole derivatives show promising growth stimulant properties, with activity ranging from 65-1000% compared to heteroauxin.

Substituent effect on oxidative cyclization of aldehyde thiosemicarbazones with ferric chloride

Aldehyde thiosemicarbazones with methyl or phenyl groups on the N-2 nitrogen atom show improved oxidative cyclization with ferric chloride, yielding 1,2,4-triazoline and 1,3,4-thiadiazoline 5 heterocyclic rings.

13C NMR spectra of 1,3,4‐thiadiazole/thiadiazoline isomeric pairs

The 13C NMR spectra of 1,3,4-thiadiazole/thiadiazoline isomers can accurately identify the isomer present, with their IR and UV spectra in agreement with azole/azoline analogues.

Reactivity of 2‐amino‐1,3,4‐thiadiazoles. Nucleophilic behaviour of some 2‐amino‐1,3,4‐thiadiazoles: Model compounds

The ambident nucleophilic behavior of some 2-amino-5-H-1,3,4-thiadiazoles in alkylation, acylation, and nitrosation reactions has been confirmed.

Reactivity of the A-CH=N=NR-CX-B System. 1,3,4-thiadiazoles and Δ2 -thiadiazolines

The A-CH=N=NR-CX-B system is reactive towards ferric chloride, forming 2-amino-5-thenoyl-1,3,4-thiadiazoles and 4-methyl-5-imino-2-thenoyl-2-1,3,4-thi

The synthesis and reactivity of some 2-amino-5-bromo-],1,3,4-thiadiazoles and the corresponding Δ2-1,3,4-thiadiazolines

2-amino-5-bromo-1,3,4-thiadiazoles show amine-imine tautomerism with their corresponding 2-1,3,4-thiadiazolines, suggesting ambidenl nucleophile behavior in alkylation, aeylation, and nitro

Tosylation of 2-(monosubstituted)amino-1,3,4-thiadiazoles

Tosylation of 2-(monosubstituted)amino-1,3,4-thiadiazoles in the presence of triethylamine produces ring-sulfonylated products, which are later isomerized to exocyclic amino-sulfony

The radiosynthesis of a 11C-labelled carbonic anhydrase inhibitor—[carbonyl-11C]acetazolamide

This study presents a method for radiosynthetically labeling carbonic anhydrase inhibitor acetazolamide with carbon-11, enabling in vivo positron emission tomography studies.