Structure of a substituted 2-thiohydantoin (original) (raw)
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J. Chem. Soc., Perkin Trans. 1, 2001
Reaction between diethyl bromomalonate and 3-phenylpyrrolidine-2-thione yielded a vinylogous urethane by the Eschenmoser sulfide contraction. However, with 3-substituted piperidine-2-thiones, sulfur was retained in the products, and a range of bicyclic heterocycles, including bicyclic ketene S,N-acetals (2-alkylidene-1,3-thiazolidin-4ones) and stable thioisomünchnones, was isolated. A novel dimeric ketene S,N-acetal was characterised by X-ray crystallography.
On Formation of Thiohydantoins from Amino Acids under Acylation Conditions
The Journal of Organic Chemistry, 2006
Reactions of glycine, alanine, and phenylalanine with acetic anhydride and ammonium thiocyanate give the 1-acetyl-2thiohydantoins 2a-c. These results appear to contradict prior literature reports pertaining to this reaction. Supporting Information Available: NMR spectra (1 H, 13 C, and COSY) of compounds 1, 2a-c, 4a-c, and 5. This material is available free of charge via the Internet at http://pubs.acs.org. JO052576I
Tetrahedron, 1974
with compound (1) gave dibenzoyl, while 2 and 3 gave the corresponding 3_oxo(ZH)thiophenes 5. With copper-bronze I gave 2,2'-di-(thiobenzoate) (4), while 2 gave 2.7diphenylthiepin (6a) and 2,5_diphenylthiophene (7a), but 3 gave only 2,5-di-(pmethoxyphenyl)thiophene (7b). With Grignard reagents 1 gave the corresponding methanol derivative 14, while 2 gave the thiobenzoylethylenes 13s and b, but 3 gave 2.7 -di -(pmethoxyphenyl) -4,4,5.5tetraphenyl(4H)thiepin (IS). The reaction mechanisms are discussed.
ACS omega, 2022
In this study, a novel heterocyclic amide derivative, N-(3-cyanothiophen-2-yl)-2-(thiophen-2-yl)acetamide (I), was obtained by reacting 2-aminothiophene-3-carbonitrile with activated 2-(thiophen-2-yl)acetic acid in a N-acylation reaction and characterized by elemental analyses, FT-IR, 1H and 13C NMR spectroscopic studies, and single crystal X-ray crystallography. The crystal packing of I is stabilized by C–H···N and N–H···N hydrogen bonds. In addition, I was investigated computationally using the density functional theory (DFT) method with the B3LYP exchange and correlation functions in conjunction with the 6311++G(d,p) basis set in the gas phase. Fukui function (FF) analysis was also carried out. Electrophilicity-based charge transfer (ECT) method and charge transfer (ΔN) were computed to examine the interactions between I and DNA bases (such as guanine, thymine, adenine, and cytosine). The most important contributions to the Hirshfeld surface are H···H (21%), C···H (20%), S···H (19%), N···H (14%), and O···H (12%). An ABTS antioxidant assay was used to evaluate the in vitro antioxidant activity of I. The compound exhibited moderate antioxidant activity. The antimicrobial activity of the title molecule was investigated under aseptic conditions, using the microdilution method, against Gram-positive and Gram-negative bacterial strains, and it also demonstrated significant activity against yeasts (Candida glabrata ATCC 90030, Candida krusei ATCC 34135). The findings revealed that the molecule possesses significant antioxidant and antimicrobial properties.
Green Chemistry, 2008
The products obtained by the reaction of 1,3-disubstituted thioureas with chloroacetylchloride are actually 2-imino-4-thiazolidinone derivatives and not thiohydantoins as previously reported (M. Kidwai, R. Venkataraman and B. Dave, Green. Chem., 2001, 3, 278). A highly efficient method for the preparation of 2-imino-4-thiazolidinones has been achieved from both symmetrical and unsymmetrical thioureas in the absence of base. The reaction gives a regioselective product for unsymmetrical thiourea which is dependent on the pK a 's of the amines. For unsymmetrical thiourea, regioselective 2-imino-4-thiazolidinone formation takes place with the amine attached to the thiourea having lower pK a as part of the imino component and the amine having higher pK a contributes to the other heterocyclic nitrogen.
Synthesis and characterization of various amino acid derived thiohydantoins
Proceedings of The 22nd International Electronic Conference on Synthetic Organic Chemistry
Hydantoins and their sulfur containing analogues, thiohydantoins, are cyclic ureides that have attracted huge attention ever since their discovery. Most of them are biologically active compounds and several points of structural diversity have made them very synthetically attractive. Although substituents can be introduced to the hydantoin nucleus, most substituted hydantoins are synthesized from substrates already containing these groups, while forming the hydantoin nucleus. This is a common route to the synthesis of hydantoins and one of them is employed in this study. A series of 3-allyl-2-thiohydantoins is synthesized from various α-amino acids in a reaction with allyl isothiocyanate. The substitution of the acquired thiohydantoin depends on the structure of the starting α-amino acid. The residual group of the α-amino acid becomes the substituent at the C5-position, while N-monosubstituted amino acids give rise to a substituent in the N1-position. The reaction is carried out in a...
Reactions with 2-methyl- and 2-styryl-4-thiochromones
Liebigs Annalen der Chemie, 1984
Diazoalkanes react with 2-methyl-and 2-styryl-4-thiochromones to yield the 1.3-dithiolanes 1 and/or ethylenes 2-4. The latter are cleaved with thionyl chloride to give the corresponding ketones, while on fusion with sulfur they afford the corresponding thioketones. By condensation with compounds containing active hydrogen, such as malononitrile and ethyl cyanoacetate, the 2-methyl-and 2-styryl-4-thiochromones yield the compounds 5. Oxidation of 2-methyl-and 2-styryl-4-thiochromones was accomplished by yellow mercury(l1) oxide as well as with tetrahaloo-benzoquinones to give the corresponding ketones. The biological activity of some selected compounds prepared during this work has been tested towards Gram-positive and Gram-negative bacteria. Reaktionen mit 2-Methyl-und 2-Styryl-4-thiochromonen Diazoalkane reagieren mit 2-Methyl-und 2-Styryl-4-thiochromonen zu 1,3-Dithiolanen 1 und/ oder Ethylencn 2-4. Letztere werden mit Thionylchlorid zu den entsprechenden Ketonen gespalten wahrend beim Schmelzen rnit Schwefel die entsprechenden Thioketone entstehen. 2-Methylund 2-Styryl-4-thiochromone kondensieren mit CH-aciden Verbindungen wie Malononitril und Cyanessigsaure-ethylester zu 5. Oxidation der 2-Methyl-und 2-Styryl-4-thiochromone rnit gelbem Quecksilber(I1)-oxid oder mit Tetrahalogen-o-benzochinon ergibt die entsprechenden Ketone. Die biologische Aktivitat ausgewahlter Verbindungen gegenuber Gram-positiven und Gramnegativen Bakterien wurde untersucht. 2 Verlag Chemie GmbH, D-6940 Weinhelm, 1984 0170-2041/84/0101-0186 S 02.50/0 6 h. The reaction mixture was filtered while hot, and the black residue was extracted several times with the appropriate solvent. The extract was concentrated, left to cool, and the solid obtained (Sad) was crystallized from ethanol to give colourless crystals. 2-(2-Methyl-4H-1-benzopyran-4-ylidene)malononitrile (Sa): m. p. 332-334"C, yield 62%. C13H8N,0 (208.2) Calc. C 74.99 H 3.87 N 13.45 Found C 75.2 H 3.8 N 13.0 2-[2-(2-Phenylethenyl)-4H-I-benzopyran-4-ylidene]malononitrile (5 b): m. p. 234-235 "C, yield 64%. C20H,,N20 (296.3) Calc. C 81.07 H 4.08 N 9.45 Found C 81.4 H 4.1 N 9.5 Ethyl 2-eyano-2-(2-methyl-4H-l-benzopyran-4-ylidene]aceiate (Sc): m. p. 125 "C, yield 61 Vo.