0000000000419190
AUTHOR
M. El Messaoudi
Formation of Pyrazol-1,3,4-Thiadiazoles through 1,3-Dipolar Cycloadditions of 3-Thioxo-[1,2,4]-Triazepin-5-one with Nitrilimines: An Experimental and Computational study
In this work the results of experimental and computational study of the title compounds and some ancillary compounds are reported. Two bicyclic pyrazol-1,3,4-thiadiazole derivatives were synthesized by reaction between 6-dimethylaminomethylene-3-thioxo-[1,2,4]- triazepin-5-one 1 and several nitrilimines 2a-f to give corresponding spirocycloadducts 3a-f, which undergo a rapid rearrangement leading to the new bicyclic compounds, 4a-f and 5a-f. These obtained bicyclic products were characterized by 1H and 13C NMR spectroscopy and finally by X-ray crystallography. Theoretical calculations have been carried out using DFT methods to rationalize the formation of the two new bicyclic compounds. Two…
A combined experimental and theoretical study of the alkylation of 3,5-dithioxo-[1,2,4]triazepines
The chemo- and regioselective alkylation reactions of 3,5-dithioxo[1,2,4]triazepine 1 in a basic medium with α,ω-dibromoalkanes 2a–c, Br(CH2)nBr (n = 1–3), are studied experimentally and theoretically. These alkylations, which occur at the thioxo sulfur atom in position 5, afford mainly 5-bromomethylthio-2,7-dimethyl- 2,3-dihydro- 4H[1,2,4]triazepin-3-one 3 for n = 1, 6,8-dimethyl-5-thioxo-2,3,4,5-tetrahydro-6H[1,3]thiazolo[4,5-d][1,2,4]triazepine 4 for n = 2 and 7,9-dimethyl-6-thioxo-2,3,4,5,6,7-hexahydro[1,3]thiazino [4,5-d][1,2,4]triazepine 5 for n = 3. Theoretical calculations have been carried out at the B3LYP/6-31G* and B3LYP(benzene)/6-311+G*//B3LYP/6-31G* levels, in order to rationa…
CCDC 206075: Experimental Crystal Structure Determination
Related Article: S.Azzouzi, R.Jalal, M.El Messaoudi, L.R.Domingo, M.Esseffar, M.J.Aurell|2007|J.Phys.Org.Chem.|20|245|doi:10.1002/poc.1145
CCDC 210903: Experimental Crystal Structure Determination
Related Article: S.Azzouzi, M.El Messaoudi, M.Esseffar, R.Jalal, F.H.Cano, M.del Carmen Apreda-Rojas, L.R.Domingo|2005|J.Phys.Org.Chem.|18|522|doi:10.1002/poc.892
CCDC 206077: Experimental Crystal Structure Determination
Related Article: S.Azzouzi, M.El Messaoudi, M.Esseffar, R.Jalal, F.H.Cano, M.del Carmen Apreda-Rojas, L.R.Domingo|2005|J.Phys.Org.Chem.|18|522|doi:10.1002/poc.892