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Organic Chemistry Including Heteroatoms

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 November 2020) | Viewed by 35458

Special Issue Editor

Special Issue Information

Dear Colleagues,

This Special Issue of Molecules on organic chemistry including heteroatoms accommodates reviews/original papers on the fields of organic chemistry and applied organic chemistry related to some kinds of heteroatom, such as N, O, S, as well as P and metals including also the corresponding heterocycles. The hot topics may embrace new synthetic methods and bioorganic chemistry connected to heteroatomic derivatives, N-, O-, and S-heterocycles, as well as organometallic and organophosphorus species. Natural product chemistry (alkaloids and flavonoids) and macrocycles including crown ethers and calixarenes are also points of interest, along with suitable aspects of catalytic and green chemistry, organocatalysis, biocatalysis, phase transfer catalysis, heterogeneous and homogeneous catalysis, P-ligands, C–C and P–C coupling reactions, click reactions, microwave chemistry, ionic liquids, flow chemistry, selective and asymmetric syntheses, as well as optical resolutions. Bioactivity studies and theoretical aspects including mechanisms also belong to the scope of the Special Issue.

Prof. Dr. György Keglevich
Guest Editor

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Keywords

  • heteroatomic organic chemistry
  • N-, O-, and S-heterocycles
  • natural products (e.g., alkaloids and flavonoids)
  • organometallic chemistry
  • organophosphorus chemistry
  • macrocycles
  • catalysts and catalysis
  • green chemistry
  • microwave chemistry
  • ionic liquids
  • coupling reactions
  • optically active species
  • flow chemistry
  • biologically active compounds
  • theoretical studies
  • mechanisms

Published Papers (11 papers)

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Research

Jump to: Review

12 pages, 1154 KiB  
Article
Novel Ring Systems: Spiro[Cycloalkane] Derivatives of Triazolo- and Tetrazolo-Pyridazines
by Csilla Sepsey Für, Gergő Riszter, Áron SzigetvárI, Miklós Dékány, György Keglevich, László HazaI and Hedvig BölcskeI
Molecules 2021, 26(8), 2140; https://doi.org/10.3390/molecules26082140 - 08 Apr 2021
Cited by 3 | Viewed by 2019
Abstract
In orderto synthesize new pyridazine derivatives anellated with different nitrogen heterocyclic moieties, spiro[cycloalkane]pyridazinones were transformed into the corresponding thioxo derivatives via a reaction with phosphorus pentasulfide. The reaction of the formed 2,3-diazaspiro[5.5] undec-3-ene-1-thiones with hydrazine provided the corresponding 1-hydrazono-2,3-diazaspiro[5.5] undec-3-ene, whose diazotization led [...] Read more.
In orderto synthesize new pyridazine derivatives anellated with different nitrogen heterocyclic moieties, spiro[cycloalkane]pyridazinones were transformed into the corresponding thioxo derivatives via a reaction with phosphorus pentasulfide. The reaction of the formed 2,3-diazaspiro[5.5] undec-3-ene-1-thiones with hydrazine provided the corresponding 1-hydrazono-2,3-diazaspiro[5.5] undec-3-ene, whose diazotization led to the desired spiro[cyclohexane-1,8-tetrazolo[1,5-b]pyridazines. The reaction of dihydropyridazinethiones with benzhydrazide afforded the corresponding 7H-spiro[[1,2,4]triazolo[4,3-b]pyridazin-8,1-cyclohexanes]. As a result of our work, seven new pyridazinethione intermediates were prepared, which served as starting materials for the synthesis of two kinds of new ring systems: tetrazolo-pyridazines and triazolo-pyridazines. The six new annulated derivatives were characterized by physicochemical parameters. The new N-heterocycles are valuable members of the large family of pyridazines. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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13 pages, 1699 KiB  
Article
2,3-Dihydroferroceno[3,4]pyrrolo[2,1-b]thiazol-5(8b)-ones: Synthesis, Structure and DFT Study on the Mechanism of Chemo- and Diastereoslective Annulations of (Sp)-2-Formylferrocenecarbonyl Fluoride and (Sp)-2-Formylferrocenecarboxylic Acid
by Zoltán Kovács and Antal Csámpai
Molecules 2021, 26(5), 1420; https://doi.org/10.3390/molecules26051420 - 05 Mar 2021
Cited by 2 | Viewed by 1892
Abstract
By means of the annulation of easy-to-handle yet sufficiently reactive (Sp)-2-formylferrocenecar- bonyl fluoride with the hydrochlorides of cysteamine and the methyl esters of enentiomer cysteines conducted in dichloromethane at room temperature in the presence of pyridine, the first members of [...] Read more.
By means of the annulation of easy-to-handle yet sufficiently reactive (Sp)-2-formylferrocenecar- bonyl fluoride with the hydrochlorides of cysteamine and the methyl esters of enentiomer cysteines conducted in dichloromethane at room temperature in the presence of pyridine, the first members of 2,3-dihydroferroceno[3,4]pyrrolo[2,1-b]thiazol-5(8bH)-ones with the elements of planar- and central chirality were prepared as single enantiomers. An atom economic procedure was also elaborated for the synthesis of these organometallic heterocycles directly exploring (Sp)-2-formylferrocenecarboxylic acid in situ activated by CDI and TFA, sequentially added to the reaction mixture. The relative and consequently, the absolute, configuration of the isolated diastereomers was determined by NMR measurements supported by DFT structural optimization. On the basis of the results of synthetic control experiments and a series of further DFT modelling studies, including energetic and MO analysis of the iminium intermediates, we propose a mechanism for the thiazolidine-forming annulations that proceed via primary N-acylation followed by proton-mediated cyclocondensation and subsequent diastereoselective sulfhydryl-attack on the resulting iminium center. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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21 pages, 3766 KiB  
Article
Synthesis, In Silico Prediction and In Vitro Evaluation of Antitumor Activities of Novel Pyrido[2,3-d]pyrimidine, Xanthine and Lumazine Derivatives
by Samar El-Kalyoubi and Fatimah Agili
Molecules 2020, 25(21), 5205; https://doi.org/10.3390/molecules25215205 - 09 Nov 2020
Cited by 18 | Viewed by 2558
Abstract
Ethyl 5-arylpyridopyrimidine-6-carboxylates 3ad were prepared as a one pot three component reaction via the condensation of different aromatic aldehydes and ethyl acetoacetate with 6-amino-1-benzyluracil 1a under reflux condition in ethanol. Additionally, condensation of ethyl 2-(2-hydroxybenzylidene) acetoacetate with 6-amino-1-benzyluracil in DMF afforded [...] Read more.
Ethyl 5-arylpyridopyrimidine-6-carboxylates 3ad were prepared as a one pot three component reaction via the condensation of different aromatic aldehydes and ethyl acetoacetate with 6-amino-1-benzyluracil 1a under reflux condition in ethanol. Additionally, condensation of ethyl 2-(2-hydroxybenzylidene) acetoacetate with 6-amino-1-benzyluracil in DMF afforded 6-acetylpyridopyrimidine-7-one 3e; a facile, operationally, simple and efficient one-pot synthesis of 8-arylxanthines 6af is reported by refluxing 5,6-diaminouracil 4 with aromatic aldehydes in DMF. Moreover, 6-aryllumazines 7ad was obtained via the reaction of 5,6-diaminouracil with the appropriate aromatic aldehydes in triethyl orthoformate under reflux condition. The synthesized compounds were characterized by spectral (1H-NMR, 13C-NMR, IR and mass spectra) and elemental analyses. The newly synthesized compounds were screened for their anticancer activity against lung cancer A549 cell line. Furthermore, a molecular-docking study was employed to determine the possible mode of action of the synthesized compounds against a group of proteins highly implicated in cancer progression, especially lung cancer. Docking results showed that compounds 3b, 6c, 6d, 6e, 7c and 7d were the best potential docked compounds against most of the tested proteins, especially CDK2, Jak2, and DHFR proteins. These results are in agreement with cytotoxicity results, which shed a light on the promising activity of these novel six heterocyclic derivatives for further investigation as potential chemotherapeutics. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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10 pages, 2528 KiB  
Article
Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
by Nikoletta Harsági, Zita Rádai, Áron Szigetvári, János Kóti and György Keglevich
Molecules 2020, 25(17), 3793; https://doi.org/10.3390/molecules25173793 - 20 Aug 2020
Cited by 6 | Viewed by 1929
Abstract
The two-step acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. [...] Read more.
The two-step acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants. The fission of the second P-O-C bond was found to be the rate-determining step. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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17 pages, 1555 KiB  
Article
Synthesis and Structure of Iron (II) Complexes of Functionalized 1,5-Diaza-3,7-Diphosphacyclooctanes
by Yulia S. Spiridonova, Yulia A. Nikolaeva, Anna S. Balueva, Elvira I. Musina, Igor A. Litvinov, Igor D. Strelnik, Vera V. Khrizanforova, Yulia G. Budnikova and Andrey A. Karasik
Molecules 2020, 25(17), 3775; https://doi.org/10.3390/molecules25173775 - 19 Aug 2020
Cited by 4 | Viewed by 2388
Abstract
In order to synthesize new iron (II) complexes of 1,5-diaza-3,7-diphosphacyclooctanes with a wider variety of the substituents on ligands heteroatoms (including functionalized ones, namely, pyridyl groups) and co-ligands, it was found that these ligands with relatively small phenyl, benzyl, and pyridin-2-yl substituents on [...] Read more.
In order to synthesize new iron (II) complexes of 1,5-diaza-3,7-diphosphacyclooctanes with a wider variety of the substituents on ligands heteroatoms (including functionalized ones, namely, pyridyl groups) and co-ligands, it was found that these ligands with relatively small phenyl, benzyl, and pyridin-2-yl substituents on phosphorus atoms in acetonitrile formed bis-P,P-chelate cis-complexes [L2Fe(CH3CN)2]2+ (BF4)2, whereas P-mesityl-substituted ligand formed only monoligand P,P-complex [LFe(CH3CN)4]2+ (BF4)2. 3,7-dibenzyl-1,5-di(1′-(R)-phenylethyl)-1,5-diaza-3,7-diphosphacyclooctane reacted with hexahydrate of iron (II) tetrafluoroborate in acetone to give an unusual bis-ligand cationic complex of the composition [L2Fe(BF4)]+ BF4, where two fluorine atoms of the tetrafluoroborate unit occupied two pseudo-equatorial positions at roughly octahedral iron ion, according to X-ray diffraction data. 1,5-diaza-3,7-diphosphacyclooctanes replaced tetrahydrofurane and one of the carbonyl ligands of cyclopentadienyldicarbonyl(tetrahydrofuran)iron (II) tetrafluoroborate to form heteroligand complexes [CpFeL(CO)]+BF4. The structural studies in the solid phase and in solutions showed that diazadiphosphacyclooctane ligands of all complexes adopted chair-boat conformations so that their nitrogen atoms were in close proximity to the central iron ion. The redox properties of the obtained complexes were performed by the cyclic voltammetry method. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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14 pages, 2123 KiB  
Article
The Chiral 1:2 Adduct (S)S(S)C(−)589-Ethyl 2-Phenylbutyl Sulphide-Mercury (II) Chloride:(−)589[(S)S(S)C-Et(2-PhBu)S.(HgCl2)2]. Stereoselective Synthesis, Asymmetric Oxidation, Crystal and Molecular Structure and Circular Dichroism Spectra
by Paolo Biscarini, Ivano Bilotti, Francesco Ferranti, Alessia Bacchi, Giancarlo Pelizzi, Marian Mikołajczyk and Jozef Drabowicz
Molecules 2020, 25(15), 3398; https://doi.org/10.3390/molecules25153398 - 27 Jul 2020
Viewed by 1973
Abstract
Optically active (−)589ethyl (S)-2-phenylbutyl thioether, (−)(S)C-Et(PhBu)S (I), and its new diastereoisomeric mercury (II) chloride adduct, 1:2, (−)[(S)S(S)C-Et(PhBu)S.(HgCl2)2]2, (II [...] Read more.
Optically active (−)589ethyl (S)-2-phenylbutyl thioether, (−)(S)C-Et(PhBu)S (I), and its new diastereoisomeric mercury (II) chloride adduct, 1:2, (−)[(S)S(S)C-Et(PhBu)S.(HgCl2)2]2, (II) were stereoselectively synthesized; the absorbance (UV) and circular dichroism (CD) spectra were measured and the crystal and molecular structure of complex (II) was determined by single-crystal X-ray diffraction. Two different Hg centres are present whose coordination environments are built by two short bonds to chloride ligands in one case, and to one chloride and one sulphur in the other one. These originate digonal units. Electroneutrality is achieved by a further chlorine, which can be considered prevalently ionic and bonded to the two Hg centres, forming square bridging systems nearly perpendicular to the digonal molecules. The coordination polyhedra can be interpreted as 2 + 4 tetragonally-compressed octahedra with the four longer contacts lying in the equatorial plane. IR spectroscopic data are consistent with the presence of one bent and one linear Cl–Hg–Cl moiety. The absolute configurations at both stereogenic centres of the formed diastereoisomeric complex (II) are (S). The (S)S absolute configuration at the stereogenic sulphur atom bonded to the mercury(II) atom in complex (II) has been related with the negative Cotton effect assigned in its circular dichroism (CD) spectrum to a charge-transfer transition at ca. 230 nm. The stereoselective oxidation of (I) and (II) with hydrogen peroxide, induced by the stereogenic carbon atom (S)C of the enantiopure sulphide, gave (−)598ethyl (S)C-2-phenylbutyl(S)S-sulphoxide, (−)598[(S)S(S)C-Et(PhBu)SO], (III), having 18.1% de. Oxidations carried out in the presence of a 200 molar excess of mercury(II) chloride gave (−)598ethyl (S)C-2-phenylbutyl(R)S-sulphoxide, (−) 598[(R)S(S)C-Et(PhBu)SO], (IV) with 31% de, showing the cooperative influence of mercury(II) chloride on the selectivity of the oxidation reaction. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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21 pages, 5847 KiB  
Article
Novel Convenient Approach to 6-, 7-, and 8-Numbered Nitrogen Heterocycles Incorporating Endocyclic Sulfonamide Fragment
by Oleksandr Shalimov, Eduard Rusanov, Oksana Muzychka and Petro Onys’ko
Molecules 2020, 25(12), 2887; https://doi.org/10.3390/molecules25122887 - 23 Jun 2020
Cited by 3 | Viewed by 2982
Abstract
A new effective method for the construction of nitrogen heterocycles incorporating endocyclic pharmacophore sulfonamide fragment, based on the use of easy accessible N-(chlorosulfonyl)imidoyl chloride, CCl3C(Cl)=NSO2Cl (1), has been developed. Thus, a reaction of 1 as bielectrophilic [...] Read more.
A new effective method for the construction of nitrogen heterocycles incorporating endocyclic pharmacophore sulfonamide fragment, based on the use of easy accessible N-(chlorosulfonyl)imidoyl chloride, CCl3C(Cl)=NSO2Cl (1), has been developed. Thus, a reaction of 1 as bielectrophilic 1,3-C–N–S reagent with benzylamines that act as 1,4-N–C–C-C binucleophiles, affords respective 1,2,4-benzothiadiazepine-1,1-dioxides. On the other hand, 1 reacts with alkenyl amines with the formation of respective N-alkenyl amidines undergoing Lewis acids initiated intramolecular cyclization to afford derivatives of 1,2,4-thiadiazines and 1,2,4-thiadiazocines bearing a halomethyl group able for further functionalization. The first examples of electrophilic heterocyclization of the chlorosulfonyl group onto an alkenyl or alkynyl group have been revealed. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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19 pages, 2120 KiB  
Article
[1,5]-Hydride Shift-Cyclization versus C(sp2)-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4- and 1,5-Benzoxazepines
by Dóra Szalóki Vargáné, László Tóth, Balázs Buglyó, Attila Kiss-Szikszai, Attila Mándi, Péter Mátyus, Sándor Antus, Yinghan Chen, Dehai Li, Lingxue Tao, Haiyan Zhang and Tibor Kurtán
Molecules 2020, 25(6), 1265; https://doi.org/10.3390/molecules25061265 - 11 Mar 2020
Cited by 4 | Viewed by 4263
Abstract
Domino cyclization reactions of N-aryl-1,4- and 1,5-benzoxazepine derivatives involving [1,5]-hydride shift or C(sp2)-H functionalization were investigated. Neuroprotective and acetylcholinesterase activities of the products were studied. Domino Knoevenagel-[1,5]-hydride shift-cyclization reaction of N-aryl-1,4-benzoxazepine derivatives with 1,3-dicarbonyl reagents having active methylene group [...] Read more.
Domino cyclization reactions of N-aryl-1,4- and 1,5-benzoxazepine derivatives involving [1,5]-hydride shift or C(sp2)-H functionalization were investigated. Neuroprotective and acetylcholinesterase activities of the products were studied. Domino Knoevenagel-[1,5]-hydride shift-cyclization reaction of N-aryl-1,4-benzoxazepine derivatives with 1,3-dicarbonyl reagents having active methylene group afforded the 1,2,8,9-tetrahydro-7bH-quinolino [1,2-d][1,4]benzoxazepine scaffold with different substitution pattern. The C(sp3)-H activation step of the tertiary amine moiety occurred with complete regioselectivity and the 6-endo cyclization took place in a complete diastereoselective manner. In two cases, the enantiomers of the chiral condensed new 1,4-benzoxazepine systems were separated by chiral HPLC, HPLC-ECD spectra were recorded, and absolute configurations were determined by time-dependent density functional theory- electronic circular dichroism (TDDFT-ECD) calculations. In contrast, the analogue reaction of the regioisomeric N-aryl-1,5-benzoxazepine derivative did not follow the above mechanism but instead the Knoevenagel intermediate reacted in an SEAr reaction [C(sp2)-H functionalization] resulting in a condensed acridane derivative. The AChE inhibitory assays of the new derivatives revealed that the acridane derivative had a 6.98 μM IC50 value. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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19 pages, 1499 KiB  
Article
Synthesis and Cytotoxic Activity of New Vindoline Derivatives Coupled to Natural and Synthetic Pharmacophores
by András Keglevich, Leonetta Dányi, Alexandra Rieder, Dorottya Horváth, Áron Szigetvári, Miklós Dékány, Csaba Szántay, Jr., Ahmed Dhahir Latif, Attila Hunyadi, István Zupkó, Péter Keglevich and László Hazai
Molecules 2020, 25(4), 1010; https://doi.org/10.3390/molecules25041010 - 24 Feb 2020
Cited by 11 | Viewed by 4018
Abstract
New Vinca alkaloid derivatives were synthesized to improve the biological activity of the natural alkaloid vindoline. To this end, experiments were performed to link vindoline with various structural units, such as amino acids, a 1,2,3-triazole derivative, morpholine, piperazine and N-methylpiperazine. The structure of [...] Read more.
New Vinca alkaloid derivatives were synthesized to improve the biological activity of the natural alkaloid vindoline. To this end, experiments were performed to link vindoline with various structural units, such as amino acids, a 1,2,3-triazole derivative, morpholine, piperazine and N-methylpiperazine. The structure of the new compounds was characterized by NMR spectroscopy and mass spectrometry (MS). Several compounds exhibited in vitro antiproliferative activity against human gynecological cancer cell lines with IC50 values in the low micromolar concentration range. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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Review

Jump to: Research

30 pages, 16156 KiB  
Review
The Usefulness of Trivalent Phosphorus for the Synthesis of Dendrimers
by Anne-Marie Caminade, Kathleen I. Moineau-Chane Ching and Béatrice Delavaux-Nicot
Molecules 2021, 26(2), 269; https://doi.org/10.3390/molecules26020269 - 07 Jan 2021
Cited by 4 | Viewed by 6337
Abstract
Dendrimers are hyperbranched macromolecules, which are synthesized step-by-step by the repetition of a series of reactions. While many different types of dendrimers are known, this review focusses on the use of trivalent phosphorus derivatives (essentially phosphines and phosphoramidites) for the synthesis of dendrimers. [...] Read more.
Dendrimers are hyperbranched macromolecules, which are synthesized step-by-step by the repetition of a series of reactions. While many different types of dendrimers are known, this review focusses on the use of trivalent phosphorus derivatives (essentially phosphines and phosphoramidites) for the synthesis of dendrimers. The first part presents dendrimers constituted of phosphines at each branching point. The other parts display the use of trivalent phosphorus derivatives during the synthesis of dendrimers. Different types of reactions have been applied to phosphines. The very first examples of phosphorus-containing dendrimers were obtained by the alkylation of phosphines. Then, several families of dendrimers were elaborated by reaction of phosphoramidites. Such a type of reaction is the base of the solid phase synthesis of oligonucleotides; it has been applied in particular for the synthesis of dendrimers constituted of oligonucleotides. Finally, the Staudinger reaction between phosphines and azides afforded different families of dendrimers, and was at the origin of accelerated methods of synthesis of dendrimers. Besides, the reactivity of the P=N-P=S linkages created by this reaction led to very original dendritic structures. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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54 pages, 18894 KiB  
Review
Chemistry of Substituted Thiazinanes and Their Derivatives
by Alaa A. Hassan, Stefan Bräse, Ashraf A. Aly and Hendawy N. Tawfeek
Molecules 2020, 25(23), 5610; https://doi.org/10.3390/molecules25235610 - 28 Nov 2020
Cited by 5 | Viewed by 3403
Abstract
Thiazinanes and its isomeric forms represent one of the most important heterocyclic compounds, and their derivatives represented a highly potent drug in disease treatment such as, 1,1-dioxido-1,2-thiazinan-1,6-naphthyridine, which has been shown to have anti-HIV activity by a mechanism that should work as anti-AIDS [...] Read more.
Thiazinanes and its isomeric forms represent one of the most important heterocyclic compounds, and their derivatives represented a highly potent drug in disease treatment such as, 1,1-dioxido-1,2-thiazinan-1,6-naphthyridine, which has been shown to have anti-HIV activity by a mechanism that should work as anti-AIDS treatment, while (Z)-methyl 3-(naphthalen-1-ylimino)- 2-thia-4-azaspiro[5 5]undecane-4-carbodithioate showed analgesic activity, cephradine was used as antibiotic and chlormezanone was utilized as anticoagulants. All publications were interested in the chemistry of thiazine (partially or fully unsaturated heterocyclic six-membered ring containing nitrogen and sulfur), but no one was dealing with thiazinane itself which encouraged us to shed new light on these interesting heterocycles. This review was focused on the synthetic approaches of thiazinane derivatives and their chemical reactivity. Full article
(This article belongs to the Special Issue Organic Chemistry Including Heteroatoms)
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