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Here we report a metal‐free direct C−H trifluoromethylation of the imidazothiazoles 7(a–ad) using sodium triflouromethanesulfinate (Langlois' reagent) and tert‐butyl hydroperoxide (TBHP) as an oxidant. The control studies show that the protocol follows the radical reaction pathway and provides excellent yields of trifluoromethylated products 9(a–ad) with broad substrate scope and regioselective operation. Moreover, the newly synthesized compounds exhibit promising antimycobacterial activity. [ABSTRACT FROM AUTHOR]

4-(4-nitrophenyl)thiomorpholine, the title compound, has been used as a precursor for the corresponding 4-thiomorpholinoaniline, which is a useful building block in medicinal chemistry. The crystal and molecular structures of the title compound, however, have not been described thus far. We synthesized the title compound by means of a nucleophilic aromatic substitution reaction of 4-fluoronitrobenzene and thiomorpholine and structurally characterized it by X-ray crystallography, DFT calculations, and Hirshfeld surface analysis. In the crystal, the molecule exhibits an approximately CS-symmetric structure, with the nitrogen-bound 4-nitrophenyl group in a quasi axial position on the six-membered thiomorpholine ring in a low-energy chair conformation. The solid-state structure of the title compound is markedly different from that of its morpholine analogue. This can be ascribed to the formation of centrosymmetric dimers through intermolecular C–H···O weak hydrogen bonds involving the methylene groups adjacent to the sulfur atom and face-to-face aromatic stacking. [ABSTRACT FROM AUTHOR]

The development of new selective fluorogenic probes for monitoring microbiological objects and cellular compartments may help to determine the mechanism of pathogenesis of new pathogens in living cells. The easy and reliable synthetic strategy for the direct preparation of chemically pure styryl dye (E)-3-heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide is described. The photophysical properties in different solvents and in water medium neat and in the presence of the dsDNA and RNA of the dye is demonstrated and compared with that of the known structure analogue. The cellular uptake and the ability to bind cell organelles is determined. The introduction of a heptyl substituent attached to the quaternary nitrogen atom of the benzothiazole ring leads to an improvement in the photophysical properties of the dye. [ABSTRACT FROM AUTHOR]

(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical properties of the dye in a TE buffer in the absence and presence of double-stranded DNA (dsDNA) were elucidated. The low intrinsic fluorescence of 1 in TE buffer is followed by an increase in the fluorescence after dsDNA binding. The dye is nontoxic for stem cells from apical papilla and the most concentrated fluorescence is detected in the cell nucleoli. [ABSTRACT FROM AUTHOR]

A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs. [ABSTRACT FROM AUTHOR]

3-Aryl-2-bromopropanoic acid esters reacted with o-phenylenediamine, 2-sulfanylaniline, and L-cysteine to give quinoxaline, 1,4-thiazine, and thiomorpholine derivatives, respectively, containing an aryl-methyl substituent. Analogous 1,4-benzoxazine derivatives were synthesized by reactions of 3-aryl-2-bromo-propanoyl chlorides with 2-aminophenol or 2-methoxyaniline. [ABSTRACT FROM AUTHOR]

4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones reacted with morpholine and thiomorpholine in ethyl acetate to give in a few minutes 3-(morpholin-4-yl)- and 3-(thiomorpholin-4-yl)-substituted 4-halofuro-[3,4-c]pyridin-1(3H)-ones. [ABSTRACT FROM AUTHOR]

S,S- and S,S,S-substituted nitrodienes3a,3b, and4awere synthesized by reactions of 1,1,2,4,4-pentachloro-3-nitro-1,3-butadiene with some thiols 4-chlorobenzylmercaptan and 2-chlorobenzylmercaptan in ethanol in the presence of sodium hydroxide. Thiomorpholine ring substituted nitrodienes6cand6dand were obtained from the reactions of the mono(thio)substituted nitrodienes with thiomorpholine in dichloromethane. The single crystal X-ray structure of 4-(1-thiomorpholinyl)-4-(butylsulfanyl)-1,1,2-trichloro-3-nitro-1,3-butadiene (6c) is reported. In this present paper, the structures of new compounds were characterized by using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and Fourier transform infrared (FTIR) spectroscopy spectroscopic data. [ABSTRACT FROM AUTHOR]

It has been shown that various combinations of nucleophilic aromatic substitution of hydrogen (S), S and the microwave-assisted Suzuki cross-coupling reactions are a versatile method for the synthesis of 5-(het)aryl-2-(thio)morpholinopyrimidine and 4,5-di(het)aryl-2-(thio)morpholinopyrimidine derivatives. All synthesized pyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis HRv. [ABSTRACT FROM AUTHOR]

Polyhalogenated-2-nitro-1, 3-butadienes are important synthetic precursors for a variety of polyfunctionalized bioactive heterocycles. Herein, we report the reactions of 1, 1, 3, 4, 4-pentachloro-2-nitro-1, 3-butadiene 1 and 4-bromo-1, 1, 3, 4-tetrachloro-2-nitro-1, 3-butadiene 2 with amino and thiol containing nucleophiles to obtain highly functionalized (E)-polyhalodiene-2-nitro-1, 3-butadiene derivatives. Most of these reactions were found to be highly selective resulting in good to high yields of the products. All new compounds have been characterized by nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS) and Fourier transform infrared spectroscopy (FT-IR) spectroscopic data. Single crystal X-ray structure analysis of compound 8c is reported. [Figure not available: see fulltext.] [ABSTRACT FROM AUTHOR]

Die Umwandlung von Aldehyden in N ‐ unsubstituierte 3 ‐ Thiomorpholine bildet eine einfache Alternative zu metallkatalysierten Kreuzkupplungen, die zur Funktionalisierung gesättigter N ‐ Heterocyclen im Allgemeinen ungeeignet sind. Eine kupfervermittelte radikalische Cyclisierung ist der Schlüssel für die milden Bedingungen, die hohe Verträglichkeit mit funktionellen Gruppen und den großen Substratbereich, den diese Reagentien bieten. [ABSTRACT FROM AUTHOR]

N,S-Substituted nitrobutadienes 3a-g were synthesized from the reaction of the thiosubstituted derivatives 1a-g with thiomorpholine 2. The N,S-substituted nitrobutadienes 5a-g were obtained from the reaction of the thiosubstituted butadienes 1a-g with N-diphenylmethyl piperazine 4. The structure of butadiene 3c was elucidated by single crystal X-ray diffraction. [ABSTRACT FROM AUTHOR]

A screening of lignin-degrading basidial fungi that can grow in the presence of thiomorpholine derivatives (the mixture of 1,4-perhydrothiazines) has been performed. Strain Bjerkandera adusta VKM F-3477 was shown to have the maximal rate of growth in the presence of these compounds, and its capacity for thiomorpholine degradation was studied. The methods of quantitative analysis of thiomorpholine and its degradation products on the basis of thin layer chromatography and high-performance liquid chromatography were developed. It was shown that the B. adusta strain did not utilize thiomorpholine as a carbon source but transformed it into thiomorpholine sulfoxide that accumulated in the medium. Mn peroxidase produced by B. adusta in the course of thiomorpholine transformation is not directly involved in its oxidation. [ABSTRACT FROM AUTHOR]

Compound 3 and 5a , b were obtained from the reaction of 1,3,4,4-tetrachloro-1-thioallyl-2-nitro-1,3-butadiene ( 1 ) with thiomorpholine ( 2 ) and piperazine derivatives 4a , b in dichloromethane. The reaction of compound 1 and bromine gave compound 6 . Compounds 8 and 10 were obtained from the reaction of 6 with 1-(diphenylmethyl)piperazine ( 7 ) and piperidine ( 9 ) in dichloromethane. The derivative 13 was synthesized from the reaction of 4-bromo-1,1,3,4-tetrachloro-2-nitro-1,3-butadiene ( 11 ) and allylmercaptane ( 12 ). Compounds 15 and 16a , b were obtained from the reaction of 1-allyl-4-bromo-1,3,4-trichloro-2-nitro-1,3-butadiene ( 13 ) with morpholine ( 14 ) and the piperazine derivatives 16a , b , in dichloromethane, respectively. [ABSTRACT FROM AUTHOR]

Spectrophotometric assays of Mycobacterium aurum MO1 cells extracts gave evidence of a soluble cytochrome P450, involved in the degradative pathway of morpholine, a waste product from the chemical industry.In order to get further information, the kinetics of the biodegradation of the sulfur analogue thiomorpholine was monitored by using in situ nuclear magnetic resonance (NMR). This technique allowed the identification of two intermediates: the sulfoxide of thiomorpholine resulting from S-oxidation and thiodiglycolic acid owing to ring cleavage. The S-oxidation (S r SO) represents one of the well-known reactionscatalyzed by cytochromes P450. The inhibitory effect of metyrapone, a cytochrome P450 inhibitor, on the thiomorpholine and morpholine degradative abilities of M. aurum MO1 confirmed the involvement of a cytochrome P450. These results and the decrease of the rate of formationof the first intermediate during the morpholine degradation, 2-(2-aminoethoxy) acetate, proved the key role of the cytochrome P450 in theearly events of the biodegradation, i.e., in the C--N bond cleavage. [ABSTRACT FROM AUTHOR]