Synthesis of novel 2-aryl-3-(2-morpholinoethyl)-1,3-thiazinan-4-ones via ultrasound irradiation

This study describes the synthesis of fourteen thiazinanones from a multicomponent reaction of 2-morpholinoehtylamine (as primary amine), arenealdehydes (as carbonyl compound) and the mercaptopropionic acid using both conventional (thermal heating) and ultrasound methodologies. Through thermal heating methodology, the thiazinanones were obtained in 49 to 97% yields for 16 hours and through sonochemistry methodology, the reaction time was reduced for 25 minutes with yields 41 to 88%. The full identification and characterization of unpublished heterocycles were achieved by proton (1H) and carbon 13 (13C) nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry and infrared. Some of them were also characterized by elemental analysis27611091115CONSELHO NACIONAL DE DESENVOLVIMENTO CIENTÍFICO E TECNOLÓGICO - CNPQCOORDENAÇÃO DE APERFEIÇOAMENTO DE PESSOAL DE NÍVEL SUPERIOR - CAPESFUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE SÃO PAULO - FAPESPFUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DO RIO GRANDE DO SUL - FAPERGS307330/2012-5Sem informação2013/18203-511/2068-

4-(Pyrimidin-2-yl)-1-thia-4-aza­spiro­[4.5]decan-3-one

The title compound, C12H15N3OS, features an envelope conformation for the 1,3-thia­zolidin-4-one ring with the S atom as the flap atom. The pyrimidine ring is almost orthogonal to the 1,3-thia­zolidin-4-one ring as indicated by the N—C—C—N torsion angle of −111.96 (18)°. Supra­molecular dimers are formed in the crystal structure through the agency of C—H⋯O contacts occurring between centrosymmetrically related mol­ecules. These are linked into supra­molecular tapes along [100] via C—H⋯S contacts

(E)-1-(2,4-Dinitro­phen­yl)-2-pentyl­idenehydrazine

The title compound, C11H14N4O4, is essentially planar with an r.m.s. deviation for the 19 non-H atoms of 0.152 Å. The conformation about the C=N bond is E, and the mol­ecule has a U-shape as the butyl group folds over towards the aromatic system. An intra­molecular C—H⋯N inter­action occurs. The crystal packing is dominated by N—H⋯O hydrogen bonding and C—H⋯O contacts, leading to twisted zigzag supra­molecular chains along the c direction. The crystal packing brings two nitro O atoms into an unusually close proximity of 2.686 (4) Å. While the nature of this inter­action is not obvious, there are several precendents for such short nitro–nitro O⋯O contacts of less than 2.70 Å in the crystallographic literature

Aplicação de α-oxoceteno ditiocetais em síntese orgânica Reactivity of α-oxoketene dithiocetals in organic synthesis

<abstract language="eng">The synthesis and reactivity of &#945;-oxoketenes dithioacetals (S,S-acetals), general structure [(R¹C=OC(R²)=C(SR³)(SR4)], are reported. We also showed the application of S,S acetals as synthons for efficient synthesis of isoxazoles, pyrazoles, indazoles, thiophenes, dithiol thiones, pyridines, pyrimidines and other heterocycles. This work aims to review the importance of &#945;-oxoketenes dithioacetals in organic chemistry during the past few years

Synthesis of Novel 2-Aryl-3-(2-morpholinoethyl)-1,3-thiazinan-4-ones Via Ultrasound Irradiation

This study describes the synthesis of fourteen thiazinanones from a multicomponent reaction of 2-morpholinoehtylamine (as primary amine), arenealdehydes (as carbonyl compound) and the mercaptopropionic acid using both conventional (thermal heating) and ultrasound methodologies. Through thermal heating methodology, the thiazinanones were obtained in 49 to 97% yields for 16 hours and through sonochemistry methodology, the reaction time was reduced for 25 minutes with yields 41 to 88%. The full identification and characterization of unpublished heterocycles were achieved by proton ( 1 H) and carbon 13 ( 13 C) nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry and infrared. Some of them were also characterized by elemental analysis

Toxicological Evaluation of Anti-Scrapie Trimethoxychalcones and Oxadiazoles

An altered form of the cellular prion protein, the PrPScor PrPRes, is implicated in the occurrence of the still untreatable transmissible spongiform encephalopathies. We have previously synthesized and characterized aromatic compounds that inhibit protease-resistant prion protein (PrPRes) accumulation in scrapie-infected cells. These compounds belong to different chemical classes, including acylhydrazones, chalcones and oxadiazoles. Some of the active compounds were non-toxic to neuroblastoma cells in culture and seem to possess drugable properties, since they are in agreement with the Lipinski´s rule of 5 and present desirable pharmacokinetic profiles as predicted in silico. Before the evaluation of the in vivo efficacy of the aromatic compounds in scrapie-infected mice, safety assessment in healthy mice is needed. Here we used Swiss mice to evaluate the acute toxicity profile of the six most promising anti-prionic compounds, the 2,4,5-trimethoxychalcones (J1, J8, J20 and J35) and the 1,3,4-oxadiazoles (Y13 and Y17). One single oral administration (300 mg/kg) of J1, J8, J20, J35, Y13 and Y17 or repeated intraperitoneal administration (10 mg/kg, 3 times a week, for 4 weeks) of J1, J8 and J35, did not elicit toxicity in mice. We strongly believe that the investigated trimethoxychalcones and oxadiazoles are interesting compounds to be further analyzed in vivo against prion diseases