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Journal articles on the topic 'Oxirane derivatives'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Petrosyan, Artyom V., Astghik A. Shahkhatuni, Andranik M. Davinyan, et al. "Thiol-Epoxy Click Chemistry: The Synthesis of Vicinal Amino Alcohols Containing a 1,2,4-Triazole Ring." Chemistry 7, no. 2 (2025): 53. https://doi.org/10.3390/chemistry7020053.

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As examples of “Click Chemistry”, the reaction of 1-(oxiran-2-ylmethyl)piperidine with several 1,2,4-triazoles derivatives was studied. As a result, the reaction shows that the oxirane ring opens regiospecifically, according to Krasusky’s rule, without using a catalyst. The basic nitrogen present in 1-(oxiran-2-ylmethyl)piperidine has a catalytic (anchimer) effect.

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2

Fernandes, Maria José G., David M. Pereira, Renato B. Pereira, A. Gil Fortes, Elisabete M. S. Castanheira, and M. Sameiro T. Gonçalves. "Synthesis and Insecticidal Activity of O-alkylated Oxirane Eugenol Derivatives." Chemistry Proceedings 3, no. 1 (2020): 36. http://dx.doi.org/10.3390/ecsoc-24-08335.

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The synthesis of three O-alkylated eugenol derivatives, bearing a hydroxypropyl chain and propyl esters, were synthesized and further converted into the corresponding oxiranes. Oxirane derivatives were then evaluated against their effect upon the viability of the insect cell line Sf9 (Spodoptera frugiperda), in comparison with the starting O-alkylates. The results pointing to their potential as bioinsecticides, with structural changes eliciting significant effects in terms of potency.

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3

Khalili, Gholamhossein, Patrick McCosker, Timothy Clark, and Paul Keller. "Synthesis and Density Functional Theory Studies of Azirinyl and Oxiranyl Functionalized Isoindigo and (3Z,3’Z)-3,3’-(ethane-1,2-diylidene)bis(indolin-2-one) Derivatives." Molecules 24, no. 20 (2019): 3649. http://dx.doi.org/10.3390/molecules24203649.

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The design and synthesis of functionalized isoindigo compounds by reaction of isoindigo with (S)-glycidyl tosylate, epibromohydrin, 2-(bromomethyl)-1-(arylsulfonyl)aziridine, and 2-(bromomethyl)-1-(alkylsulfonyl)aziridine in the presence of MeONa proceed under mild conditions in moderate yields. (3Z,3’Z)-3,3’-(Ethane-1,2-diylidene)bis(1-(oxiran-2-ylmethyl)indolin-2-one), with an extended central olefin π-conjugated moiety was also reacted with methyl-oxiranes to give the corresponding N,N’-disubstituted derivative. Calculations with DFT and TD-DFT of hypothetical isoindigo-thiophene DA molecul

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4

Sedenkova, Kseniya N., Olga V. Ryzhikova, Svetlana A. Stepanova, et al. "Bis(oxiranes) Containing Cyclooctane Core: Synthesis and Reactivity towards NaN3." Molecules 27, no. 20 (2022): 6889. http://dx.doi.org/10.3390/molecules27206889.

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Reactions of oxirane ring opening provide a powerful tool for regio- and stereoselective synthesis of polyfunctional and heterocyclic compounds, widely used in organic chemistry and drug design. Cyclooctane, alongside other medium-sized rings, is of interest as a novel molecular platform for the construction of target-oriented leads. Additionally, cyclooctane derivatives are well known to be prone to transannular reactions, which makes them a promising object in the search for novel approaches to polycyclic structures. In the present work, a series of cyclooctanediones was studied in Corey-Cha

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5

Barmaki, Mohammad, Gulgaz Valiyeva, Abel A. Maharramovm, and Mirze M. Allaverdiyev. "Synthesis of 2,3-Dihydro-6-methyl-2-thiopyrimidin-4(1H)-one (6-Methylthiouracil) Derivatives and Their Reactions." Journal of Chemistry 2013 (2013): 1–6. http://dx.doi.org/10.1155/2013/176213.

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The synthesis and characterization of 2,3-dihydro-6-methyl-2-thioxopyrimidin-(1H)-one (I) and some of its derivatives has been performed in our lab. Ring-closing cyclization, as a result of the condensation of ethyl-3-oxobutanoate with thiourea in KOH in an ethanol medium produced 2,3-dihydro-6-methy -2-thioxopyrimidin-(1H)-one (I). The reaction of compound (I) with 2- chloroacetic acid in an alkaline KOH solution produced the carboxylate derivative, 2-(2,6-dihydro-4-methyl-6-oxopyrimidin-2-yl-thio)ethanoic acid (II). The reaction of the resulted derivative of carboxylate (II) with the salt of

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6

Janeba, Zlatko, Antonín Holý, and Milena Masojídková. "Transformation of 8-[(2-Hydroxyalkyl)sulfanyl]adenines to 6-Amino-7H-purin-8(9H)-one Derivatives." Collection of Czechoslovak Chemical Communications 66, no. 9 (2001): 1393–406. http://dx.doi.org/10.1135/cccc20011393.

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Alkylation of 6-amino-7H-purin-8(9H)-thione (8-sulfanyladenine, 1) with one equivalent of (R)-[(trityloxy)methyl]oxirane gave its S-alkyl derivative 2, which was converted to the 6-amino-7H-purin-8(9H)-one (3), while alkylation of 1 with two equivalents of (S)-[(trityloxy)methyl]oxirane afforded a mixture of N3,S-dialkylated product 4a, N9-monoalkyl and N7,N9-dialkyl derivatives of 6-amino-7H-purin-8(9H)-one, 5a and 6a, respectively. This approach can be used for rapid and easy transformation of 8-[(2-hydroxyalkyl)sulfanyl]adenines to the derivatives of 6-amino-7H-purin-8(9H)-one (8-hydroxyade

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7

K., H. Popat, H. Purohit D., T. Chovatia P., and S. Joshi H. "Synthesis of some thiosemicarbazone and oxirane derivatives as potent antitubercular agents." Journal of Indian Chemical Society Vol. 82, Oct 2005 (2005): 940–41. https://doi.org/10.5281/zenodo.5827255.

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Department of Chemistry, Saurashtra University, Rajkot-360 005, India <em>E-mail</em> : drhsjoshi@yahoo.com                            <em>Fax</em>: 91-281-2578512 <em>Manuscript received 13 August 2004, revised 7 July 2005, accepted 14 July 2005</em> Condensation of thiosemicarbazide with 1-aryl-3-(3'-chlorophenyl)-2-propene-1-ones (la-j) afforded corresponding 4-α( 3'-chlorostyryl)-benzylidene-thiosemicarbazones (2a-j) and the compounds (1a-j) on reaction with alkaline H<sub>2</sub>O<sub>2</sub> gave 3-(3&#39

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8

Kuş, Melih, Cenk Omur, Sıla Karaca, and Levent Artok. "Iron-Promoted 1,5-Substitution Reaction of Endocyclic Enyne Oxiranes with MeMgBr: A Stereoselective Method for the Synthesis of Exocyclic 2,4,5-Trienol Derivatives." Chemistry 5, no. 4 (2023): 2682–99. http://dx.doi.org/10.3390/chemistry5040173.

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The iron-promoted 1,5-substitution reaction of endocyclic oxiranes with MeMgBr yields exocyclic 2,4,5-trienols with high diastereomeric ratios of up to 100:0. However, for the method’s success, the oxirane ring must have a trans-configuration. The reactions exhibit strong stereoselectivity concerning the methylation mode and the configuration of the resulting exocyclic double bond. Enantiomerically pure enyne oxiranes can be synthesized through Sharpless asymmetric dihydroxylation and subsequent manipulations. With these reagents, it has been possible to produce exocyclic 2,4,5-trienols in ena

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9

Okopi, S. O., and L. M. Affiku. "Synthesis and Olfactory Characteristics of Hydroxyether Derivatives of Methyl Eugenol." Journal of Applied Sciences and Environmental Management 24, no. 9 (2020): 1503–7. http://dx.doi.org/10.4314/jasem.v24i9.3.

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Methyl eugenol is a naturally occurring substance found in the essential oils of several plant species. It is a cheap and abundant material with a rather limited interest as perfuming ingredient. This research investigated the structure-odour relationship of methyl eugenol and its derivatives, focusing on the chemical transformation of the double bond to hydroxyether derivatives in a controlled manner. Two derivatives 2-(4-ethyl- 3-methoxybenzyl)oxirane (68.8% yield) and 1-(3,4-dimethoxyphenyl)-3-ethoxypropan-2-ol (63.58% yield), were synthesized from methyl eugenol. This research found that t

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10

Askerov, O. V., A. F. Mamedova, and D. R. Nurullayeva. "SYNTHESIS AND PROPERTIES OF ORGANOSILICON EPISULFIDES." Azerbaijan Chemical Journal, no. 4 (December 8, 2021): 43–48. http://dx.doi.org/10.32737/0005-2531-2021-4-43-48.

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A study was made of the interaction of thiourea with saturated and unsaturated organosilicon oxiranes in absolute methyl alcohol in a medium of potassium hydroxide, and methods were developed for the synthesis of unsaturated and unsaturated organosilicon silicides with a yield of 65–75%.The studies carried out revealed that the synthesized organosilicon episulfides are very reactive compounds and can react with nucleophilic and electrophilic reagents, while forming the corresponding silicon derivatives. The IR- spectra of the products were studied. It should be noted that, when comparing the I

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11

Eshtukova-Shcheglova, E. A., K. A. Perevoshchikova, A. V. Eshtukov-Shcheglov, D. A. Cheshkov, and M. A. Maslov. "Amination of epoxides as a convenient approach for lipophilic polyamines synthesis." Fine Chemical Technologies 17, no. 4 (2022): 323–34. http://dx.doi.org/10.32362/2410-6593-2022-17-4-323-334.

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Objectives. Alkylated derivatives of polyamines are able to block the growth of cancer cells due to their embedding into the polyamine biosynthesis mechanisms. The study aimed to synthesize lipophilic derivatives of norspermine or triethylenetetramine based on the formation of a C–N bond during the opening of the oxirane ring by primary amines to expand a number of synthetic polyamine derivatives with antitumor activity.Methods. The starting compounds—glycidol alcoholate or epichlorohydrin—were reacted with hexadecyl bromide or sodium hexadecanolate to give glycidyl hexadecyl ether. The key re

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12

Skachko, Stanislav, Orest Hevus, and Larysa Dolynska. "Novel Functional Derivatives of Methyl-cis-9,10-Epoxy-Octadecanoate." Chemistry & Chemical Technology 4, no. 3 (2010): 167–70. http://dx.doi.org/10.23939/chcht04.03.167.

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The synthesis of functional derivatives of epoxystearic acid methyl ester by oxirane ring opening and transesterification of ester group has been described. Some novel surface-active and peroxide-containing compounds have been obtained. Major features of the process have been investigated and main characteristics have been determined.

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13

El-Sayed, Amira A., Maher A, El Hashash, and Sameh A. Rizk. "Ultrasonic and solvent free Synthesis of Regioselective Diastereomeric Adducts and Heterocyclic Products as antibacterial agent." JOURNAL OF ADVANCES IN CHEMISTRY 13, no. 2 (2017): 5977–88. http://dx.doi.org/10.24297/jac.v13i12.6152.

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Oxirane ring containing the carboxylic group in the Î±,Î²-position are useful intermediates in the synthesis of biologically active compounds. Epoxidation of 4-(4-acetylamino and/or bromophenyl)-4-oxo-but-2-enoic acids via ultrasound condition afforded Î±-oxirane carboxylic acid followed by regioselective diastereomeric adducts of camphor. The steric factor plays an important role in regioselectivity. Formation of oxirane and furan derivatives via ultrasonic condition was considered as key steps for synthesis of some important heterocyclic compounds. The structure of new synthesized compounds

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14

Mammadov, El Sh. "SELENOLANES, SELENATRANS AND ESTERS OF SELENIC ACID." Azerbaijan Chemical Journal, no. 4 (December 8, 2022): 95–101. http://dx.doi.org/10.32737/0005-2531-2022-4-95-101.

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It is known that selenic acid and selenium dioxide act as oxidizing agents in reactions with α-oxides when heated. The proposed paper presents data on the synthesis of organoselenium compounds based on reactions of α-oxides with selenic acid and its anhydride, where the latter act as selenation agents. It was found that in the presence of catalytic amounts of boron trifluoride esterate in the reactions of oxiranes with acid the oxirane ring opens both according to the rule and against the Krasussky rule with the formation of a mixture of α- and β- isomers of selenic acid esters. In contrast to

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15

Shen, Chuang, Xiang Guo, Jun Yu, et al. "Synthesis of 2-(phenoxymethyl)oxirane derivatives through unexpected rearrangement of oxiran-2-ylmethyl benzenesulfonates." Synthetic Communications 47, no. 4 (2017): 273–78. http://dx.doi.org/10.1080/00397911.2016.1258579.

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16

Chalupová, Šárka, Antonín Holý, and Milena Masojídková. "Synthesis of Some N4-Substituted Derivatives of 1-[(S)-3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine (HPMPC, Cidofovir)." Collection of Czechoslovak Chemical Communications 70, no. 12 (2005): 2053–65. http://dx.doi.org/10.1135/cccc20052053.

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N4-Substituted derivatives of HPMPC were synthesized in four-step synthesis which included treatment of 4-methoxypyrimidin-2(1H)-one (1) with (S)-[(trityloxy)methyl]oxirane in DMF. Condensation of intermediary 1-[2-hydroxy-3-(trityloxy)propyl]-4-methoxypyrimidin-2(1H)-one (2) with (diisopropoxyphosphoryl)methyl tosylate in the presence of sodium hydride resulted in fully protected 4-methoxypyrimidin-2(1H)-one derivative 3 which gave on reaction with an appropriate primary amine in dioxane N4-substituted products 4a-4i. The reaction with bromotrimethylsilane simultaneously cleaved the trityl gr

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17

Krečmerová, Marcela, Antonín Holý, and Milena Masojídková. "Pyrimidine Acyclic Nucleotide Analogues with Aromatic Substituents in C-5 Position." Collection of Czechoslovak Chemical Communications 72, no. 7 (2007): 927–51. http://dx.doi.org/10.1135/cccc20070927.

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NH2-protected 5-phenylcytosine and its derivatives 2a-2d were treated with (2S)-2-[(trityloxy)methyl]oxirane (3) followed by etherification with diisopropyl [(tosyloxy)methyl]phosphonate (5) in the presence of sodium hydride. The intermediary phosphonate esters 6 were debenzoylated and subsequently transformed to free phosphonic acids, i.e. (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-phenylcytosine (5-phenyl-HPMPC) derivatives (8a-8d) by the action of bromotrimethylsilane and subsequent hydrolysis. Deamination of these compounds with 3-methylbutyl nitrite afforded corresponding (S)-1-[3-hyd

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18

Solomek, Tomas, Peter Stacko, Aneesh Tazhe Veetil, Tomas Pospisil, and Petr Klan. "Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives." Journal of Organic Chemistry 75, no. 21 (2010): 7300–7309. http://dx.doi.org/10.1021/jo101515a.

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19

MANDIC, Z., A. NARANDA, N. LOPOTAR, LJ DUIC, D. IVEKOVIC, and M. TKALCEC. "Tylosin Derivatives. V. Electrochemical Opening of Oxirane Ring." Journal of Antibiotics 52, no. 12 (1999): 1143–45. http://dx.doi.org/10.7164/antibiotics.52.1143.

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20

Grabowsky, S., T. Pfeuffer, M. Weber, et al. "Electronic situation in the oxirane ring – charge density and ELF study on several oxirane derivatives." Acta Crystallographica Section A Foundations of Crystallography 64, a1 (2008): C567. http://dx.doi.org/10.1107/s0108767308081774.

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21

Dzedulionytė, Karolina, Melita Veikšaitė, Vít Morávek, et al. "Convenient Synthesis of N-Heterocycle-Fused Tetrahydro-1,4-Diazepinones." Molecules 27, no. 24 (2022): 8666. http://dx.doi.org/10.3390/molecules27248666.

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A general approach towards the synthesis of tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one, tetrahydro[1,4]diazepino[1,2-a]indol-1-one and tetrahydro-1H-benzo[4,5]imidazo[1,2-a][1,4]diazepin-1-one derivatives was introduced. A regioselective strategy was developed for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylates from easily accessible 3(5)-aryl- or methyl-1H-pyrazole-5(3)-carboxylates. Obtained intermediates were further treated with amines resulting in oxirane ring-opening and direct cyclisation—yielding target pyrazolo[1,5-a][1,4]diazepin-4-ones. A straightforward tw

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22

Saputri, Dita Ayu, Dedy Suhendra, Erin Ryantin Gunawan, and Murniati Murniati. "Effect of Acid Catalyst on Epoxydation Reaction of Nyamplung Seed Oil." Jurnal Pijar Mipa 20, no. 1 (2025): 135–40. https://doi.org/10.29303/jpm.v20i1.6338.

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Epoxy is a cyclic ether compound that contains an oxirane group and has been widely applied as a stabilizer, plasticizer in polyvinyl chloride (PVC), surfactant, pesticide raw material, and as a polymer resin coating. The raw materials in epoxy synthesis come from petroleum derivatives, which are non-renewable natural resources. Therefore, there is a need for alternative raw materials that can be renewed, such as vegetable oil. In this study, nyamplung seed oil was used. Epoxy synthesis is usually carried out using carboxylic acid epoxidation with the help of an acid catalyst. This research ai

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23

Pal’chikov, V. A. "2-(4-nitrophenyl)oxirane amino derivatives in heterocyclization reactions." Russian Journal of Organic Chemistry 51, no. 8 (2015): 1114–18. http://dx.doi.org/10.1134/s1070428015080096.

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24

Moroz, A. A., V. E. Zhulanov, M. V. Dmitriev, and A. N. Maslivets. "Synthesis of Oxirane Derivatives of 1H-Pyrrole-2,3-diones." Russian Journal of Organic Chemistry 56, no. 2 (2020): 193–96. http://dx.doi.org/10.1134/s1070428020020025.

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25

Liboska, Radek, Milena Masojídková, and Ivan Rosenberg. "Carbocyclic Phosphonate-Based Nucleotide Analogs Related to PMEA. I. Racemic trans-Configured Derivatives." Collection of Czechoslovak Chemical Communications 61, no. 2 (1996): 313–32. http://dx.doi.org/10.1135/cccc19960313.

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Racemic trans-N-(2-phosphonomethoxycycloalkyl) derivatives of heterocyclic bases, a novel type of nucleotide analogs related to 9-(2-phosphonomethoxyethyl)adenine (PMEA), are reported. The synthesis of fully protected adenine- (5), hypoxanthine- (7), guanine- (11), thymine- (13), uracil- (16) and cytosine-containing (18) carbocyclic nucleotide analogs is based on the reaction of trans-2-hydroxycycloalkyl derivatives of N-protected nucleobases (2, 10, 12, 14, 17) with diisopropyl tosyloxymethanephosphonate. Deprotection of these compounds afforded the title nucleotide analogs. The starting nucl

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26

Trtek, Tomáš, Miloslav Černý, Miloš Buděšínský, Tomáš Trnka та Ivana Císařová. "New Heterocyclic Derivatives of 2-Amino-1,6-anhydro-2-deoxy-β-D-glucopyranose Containing 1,4-Oxazepane or Azepane Ring". Collection of Czechoslovak Chemical Communications 70, № 4 (2005): 466–78. http://dx.doi.org/10.1135/cccc20050466.

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Two heterocyclic derivatives of D-glucosamine, 2-amino-1,6-anhydro-2-deoxy-2-N,4-O-(ethane1,2-diyl)-β-D-glucopyranose (13) and 2-amino-1,6-anhydro-2,4-dideoxy-2-N,4-(propane-1,3-diyl)-β-D-glucopyranose (14) were prepared from 1,6-anhydro-β-D-glucopyranose (levoglucosan) in ten steps via O-4 or C-4 substituted 1,6:2,3-dianhydro-β-D-mannopyranose derivatives 2 and 4. Selective oxirane-ring cleavage with sodium azide at C-2 followed by tosylation afforded 2-azido-2-deoxy derivatives 7 and 8 of D-gluco configuration. These were reduced to amines and, after tosylation, azepane and oxazepane N-tosyl

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27

Šála, Michal, Hubert Hřebabecký, Milena Masojídková, and Antonín Holý. "Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Pyrimidine C-Nucleoside Analogues." Collection of Czechoslovak Chemical Communications 69, no. 4 (2004): 918–32. http://dx.doi.org/10.1135/cccc20040918.

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The oxirane ring opening of 3-[(benzyloxy)methyl]-7-oxabicyclo[4.1.0]heptane with sodium salt of diethyl malonate followed by treatment with TsOH gave (3aR*,6R*,7aS*)-6-[(benzyloxy)methyl]hexahydro-1-benzofuran-2(3H)-one (3a) and (3aR*,5R*,7aS*)-5-[(benzyloxy)methyl]hexahydro-1-benzofuran-2(3H)-one (3b). Lactones 3a and 3b were formylated and then treated with thiourea or guanidine to give, after deprotection, racemic 5-[2-hydroxy-4- and 2-hydroxy-5-(hydroxymethyl)cyclohexyl]-2-thiouracil (5a and 5b) or -isocytosine (12a and 12b). Simple transformations of the 2-thiouracil derivative led to ur

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Čapek, Karel, Tomáš Vydra, and Petr Sedmera. "Oxirane-oxetane-1,4-dioxane anhydro-ring migration in sucrose derivatives." Carbohydrate Research 168, no. 1 (1987): C1—C4. http://dx.doi.org/10.1016/0008-6215(87)80021-6.

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29

Galia, M., J. C. Ronda, A. Mantecon, A. Serra, and V. Cadiz. "Synthesis and oxirane ring-opening polymerization of tetrahydrophthalimide glycidyl derivatives." European Polymer Journal 28, no. 2 (1992): 175–81. http://dx.doi.org/10.1016/0014-3057(92)90304-k.

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30

Pandya, Dhananjay, and Yogesh Naliapara. "Synthesis and Anti Lung Cancer Activity of 3-Arylspiro[oxirane-2,3'- thiochroman]-4'-one Derivatives." Letters in Organic Chemistry 16, no. 6 (2019): 517–24. http://dx.doi.org/10.2174/1570178616666181130163914.

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A series of 3-arylspiro[oxirane-2,3&#039;-thiochroman]-4&#039;-one derivatives were synthesized and characterized by spectroscopy like 1H NMR, 13C NMR, mass spectrometry and elemental analysis. They were evaluated for their anti-lung cancer activity on human lung cancer cell line A-549 in DMSO. Compounds under study were found to be potent anti-lung cancer agents with GI50 values less than 10 with respect to positive control adriamycin.

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31

Murniati, Murniati, Erin Ryantin Gunawan, Dedy Suhendra, Dina Asnawati, and Pujana Qurba. "Sintesis Senyawa-Senyawa Epoksi dari Asam Lemak Minyak Nyamplung (Calophyllum inophyllum L.)." Jurnal Riset Kimia 13, no. 1 (2022): 89–99. http://dx.doi.org/10.25077/jrk.v13i1.447.

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Epoxidation is a reaction of a carbon double bond with active oxygen, which results in the addition of an oxygen atom, converting the original double bond into a three-membered epoxide (oxirane) ring. Generally, the raw material for making epoxy comes from petroleum. Nyamplung kernel oil is a non-edible oil that can be used as an alternative raw material for making epoxy derivatives. The purpose of this study was to determine the optimum conditions and characterization of epoxy materials. The fatty acids of Nyamplung kernel oil were reacted formic acid and hydrogen peroxide with sulfuric acid

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Keglevich, András, Szabolcs Mayer, Réka Pápai, et al. "Attempted Synthesis of Vinca Alkaloids Condensed with Three-Membered Rings." Molecules 23, no. 10 (2018): 2574. http://dx.doi.org/10.3390/molecules23102574.

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Our successful work for the synthesis of cyclopropanated vinblastine and its derivatives by the Simmons–Smith reaction was followed to build up further three-membered rings into the 14,15-position of the vindoline part of the dimer alkaloid. Halogenated 14,15-cyclopropanovindoline was prepared by reactions with iodoform and bromoform, respectively, in the presence of diethylzinc. Reactions of dichlorocarbene with vindoline resulted in the 10-formyl derivative. Unexpectedly, in the case of the dimer alkaloids vinblastine and vincristine, the rearranged products containing an oxirane ring in the

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33

Hô, M., W. A. Szarek, and V. H. Smith Jr. "Theoretical studies of unusually short bond lengths in oxirane and derivatives." Journal of Molecular Structure: THEOCHEM 537, no. 1-3 (2001): 253–64. http://dx.doi.org/10.1016/s0166-1280(00)00682-5.

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34

Trincone, Antonio, and Edoardo Pagnotta. "Facile chemo-enzymatic access to monoglucosyl derivatives of 2,3-oxirane dimethanol." Tetrahedron: Asymmetry 7, no. 10 (1996): 2773–74. http://dx.doi.org/10.1016/0957-4166(96)00358-8.

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35

Carneiro, Paula F., Maria C. R. F. Pinto, Roberta K. F. Marra, et al. "Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives." European Journal of Medicinal Chemistry 108 (January 2016): 134–40. http://dx.doi.org/10.1016/j.ejmech.2015.11.020.

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Djurendić, Evgenija A., Marina P. Zaviš, Marija N. Sakač, Vesna V. Kojić, Gordana M. Bogdanović, and Katarina M. Penov Gaši. "Synthesis and Biological Evaluation of Some A,D-Ring Modified 16,17-Secoandrostane Derivatives." Collection of Czechoslovak Chemical Communications 73, no. 5 (2008): 627–36. http://dx.doi.org/10.1135/cccc20080627.

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Starting from 3β-hydroxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), the new 16,17-secoandrostane derivatives 2-11 were synthesized. Protection of the 17-oxo function of compound 1 with ethylene glycol yielded compounds 2 and 3. The Oppenauer oxidation of 2 or oxidation with H2O2 in alkaline conditions gave the respective compounds 4 and 10. Epoxidation of compound 4 yielded a mixture of 4α,5α- and 4β,5β-epoxides 5 and 6 and a mixture of 4α,5α- and 4β,5β-epoxy-carboxamides 7 and 8. Opening of the oxirane ring of a mixture of compounds 5 and 6 with formic acid afforded the 4-hydroxy derivati

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37

Bamou, Fatima Zahra, Tam Minh Le, Bettina Volford, András Szekeres, and Zsolt Szakonyi. "Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core." Molecules 25, no. 1 (2019): 21. http://dx.doi.org/10.3390/molecules25010021.

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A library of 1,2-aminoalcohol derivatives with a neoisopulegol-based octahydrobenzofuran core was developed and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The allylic chlorination of (+)-neoisopulegol, derived from natural (–)-isopulegol followed by cyclization, gave the key methyleneoctahydrobenzofuran intermediate. The stereoselective epoxidation of the key intermediate and subsequent oxirane ring opening with primary amines afforded the required 1,2-aminoalcohols. The ring closure of the secondary amine analogues with formaldehyde provided spiro-oxazolidine

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38

Montero, Vincent, Marc Montana, Omar Khoumeri, Florian Correard, Marie-Anne Estève, and Patrice Vanelle. "Synthesis, In Vitro Antiproliferative Activity, and In Silico Evaluation of Novel Oxiranyl-Quinoxaline Derivatives." Pharmaceuticals 15, no. 7 (2022): 781. http://dx.doi.org/10.3390/ph15070781.

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The quinoxaline core is a promising scaffold in medicinal chemistry. Multiple quinoxaline derivatives, such as the topoisomerase IIβ inhibitor XK-469 and the tissue transglutaminase 2 inhibitor GK-13, have been evaluated for their antiproliferative activity. Previous work reported that quinoxaline derivatives bearing an oxirane ring present antiproliferative properties against neuroblastoma cell lines SK-N-SH and IMR-32. Likewise, quinoxalines with an arylethynyl group displayed promising antineoplastic properties against glioblastoma and lung cancer cell lines, U87-MG and A549 respectively. H

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Moraga, Javier, Cristina Pinedo, Rosa Durán-Patrón, Collado Isidro G., and Rosario Hernández-Galán. "Botrylactone: new interest in an old moleculedreview of its absolute configuration and related compounds." Tetrahedron 67 (November 11, 2010): 417–20. https://doi.org/10.1016/j.tet.2010.11.022.

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The absolute configuration of botrylactone, a unique compound with an interesting polyketide lactone skeleton with two oxirane bridges previously isolated from Botrytis cinerea and described as a powerful antibiotic, has been reviewed on the basis of sign of the optical rotation, NOE experiments and NMR method. The isolation of 7-deoxybotrylactone and 5-hydroxy-7-(4-hydroxydec-2(3)-enoyl) botrylactone enables us to characterize an intriguing new family of compounds with this interesting polyketide skeleton. A common biosynthetic origin with botcinin derivatives is proposed.

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Hreczuch, Wiesław, Arkadiusz Chruściel, Karolina Dąbrowska, Martino Di Serio, and Sun Yongqiang. "Characteristics of Block Copolymers of Methyl Oxirane and Oxirane Derivatives of 2-Ethylhexanol as Obtained with KOH and Dimetalcyanide Type Catalyst." Tenside Surfactants Detergents 53, no. 3 (2016): 259–64. http://dx.doi.org/10.3139/113.110431.

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Lauro, Figueroa-Valverde, Díaz-Cedillo Francisco, Ortega-Morales Otto, et al. "Design and synthesis of four steroid-oxirane derivatives using some chemical tools." Steroids 112 (August 2016): 20–35. http://dx.doi.org/10.1016/j.steroids.2016.04.012.

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De Rycke, Nicolas, Marion Jean, Nicolas Vanthuyne, Thierry Buffeteau, and Thierry Brotin. "Enantioselective Complexation of Chiral Oxirane Derivatives by an Enantiopure Cryptophane in Water." European Journal of Organic Chemistry 2018, no. 13 (2018): 1601–7. http://dx.doi.org/10.1002/ejoc.201800142.

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43

Bubnov, Yu N., A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, and S. V. Baranin. "Oxirane-based synthesis of functionalized derivatives of 2-hydroxyalkyl-substituted organophosphorus acids." Russian Chemical Bulletin 74, no. 2 (2025): 489–502. https://doi.org/10.1007/s11172-025-4541-6.

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44

Rizk, Sameh, Ismail M. Awheda, and Fathi A. Smida. "Synthesis and DFT Study of Newly Schiff Base and Fused Heterocyclic Compounds as Antibacterial Agent." JOURNAL OF ADVANCES IN CHEMISTRY 16 (November 7, 2019): 5395–403. http://dx.doi.org/10.24297/jac.v16i0.8499.

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Treatment of 2,3-di-(4-chlorophenyl) oxirane-2,3-dicarbonitriles(1) with nitrogen nucleophiles, e.g. N2H4, NH2OH afforded pyrazole 2, 1.2oxazole 3 derivatives respectively The 3-amino pyrazole-4-one derivatives 2 can be used as a key starting materials to synthesize some important Schiff base 4 and fused heterocyclic compounds e.g. Imidazolo-[4,5-c]pyrazole 5, Pyrazolo[3,4-e]1,2,4-triazine 6, pyrazol[1,2-a] 1,3,5-triazine 7, 8 and 9. The electromeric effect of the halogen atom in the aryl moieties can be controlled upon the rate of reaction and the yield of the product. The structures of synth

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Musik, Marlena, Marcin Bartkowiak, and Eugeniusz Milchert. "Advanced Methods for Hydroxylation of Vegetable Oils, Unsaturated Fatty Acids and Their Alkyl Esters." Coatings 12, no. 1 (2021): 13. http://dx.doi.org/10.3390/coatings12010013.

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Vegetable oils and their derivatives have great potential as renewable and sustainable raw materials for the production of polyurethanes and bio-based polyols. For industry an important process is their modification. Chemical reactions that are carried out on vegetable oils and their derivatives are: transesterification, auto-oxidation, hydrogenation, epoxidation, hydroxylation, acrylation, isocyanation and others. One of the modifications are reactions performed on double bonds and/or carbonyl moieties of plants oils and their derivatives. These reactions result in products that are actively

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Yamashita, Yu, Yoichi Hirano, Akiomi Takada, Hiroshi Takikawa, and Keisuke Suzuki. "Total Synthesis of Bis-anthraquinone Antibiotic BE-43472B." Synthesis 50, no. 13 (2018): 2490–515. http://dx.doi.org/10.1055/s-0037-1610136.

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This is a full account of our synthetic endeavor on the total synthesis of bis-anthraquinone antibiotic BE-43472B, an unusual octacyclic aromatic polyketide with a bis-anthraquinone scaffold. Three key steps enabled a facile access to the anthraquinone unit corresponding to the ABCF rings; (1) cyclo-condensation or -addition of benzonitrile oxides with cyclic enone derivatives, (2) benzoin cyclization for the stereoselective ring fusion with an angular hydroxy group, and (3) pinacol rearrangement for stereoselective installation of the angular aryl group. Other keys for the success include, (4

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Iwasa, Naruhito, Katsuhito Miura, Shinji Kan, and Yoshiro Furukawa. "Ring-opening polymerization of various oxirane derivatives using organotin phosphate condensate; Selective synthesis of the polyether containing oxirane ring in the side chain." Polymer Bulletin 61, no. 2 (2008): 207–16. http://dx.doi.org/10.1007/s00289-008-0949-z.

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Xie, Yong-Xin, Xue-Yuan Liu, Lu-Yong Wu, et al. "Efficient Synthesis of Substituted 3-Iodofurans by Electrophilic Cyclization of Propargylic Oxirane Derivatives." European Journal of Organic Chemistry 2008, no. 6 (2008): 1013–18. http://dx.doi.org/10.1002/ejoc.200700963.

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Gil, Małgorzata, Beata Podkościelna, Barbara Gawdzik, Andrzej Bartnicki, Wiesław Podkościelny, and Gokhan Demirci. "Synthesis and characterization of vinyl derivatives of naphthalene-2,7-diol as a photoluminescent dopant useful in optical materials." Pure and Applied Chemistry 89, no. 1 (2017): 111–23. http://dx.doi.org/10.1515/pac-2016-1002.

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AbstractIn this study synthesis and characterization of the new methacrylic derivatives of naphthalene-2,7-diol are presented. This reaction was performed in the three stages. In first stage 2,7-NAF was reacted with dimethyl sulfate in the NaOH solutions at 0°C. Next, the obtained 2,7-NAF.Me was modified by epichlorohydrine leading to epoxide compound (2,7-NAF.Me.EP). Finally, the reaction of opening oxirane rings by methacrylic acid was carried out. The chemical structures of all derivatives were confirmed by 1H and 13C NMR. Next, copolymerization reaction with methyl methacrylate (MMA), styr

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Holý, Antonín, Ivan Votruba, Eva Tloušťová, and Milena Masojídková. "Synthesis and Cytostatic Activity of N-[2-(Phosphonomethoxy)alkyl] Derivatives of N6-Substituted Adenines, 2,6-Diaminopurines and Related Compounds." Collection of Czechoslovak Chemical Communications 66, no. 10 (2001): 1545–92. http://dx.doi.org/10.1135/cccc20011545.

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N6-Substituted adenine and 2,6-diaminopurine derivatives of 9-[2-(phosphonomethoxy)- ethyl] (PME), 9-[(R)-2-(phosphonomethoxy)propyl] [(R)-PMP] and enantiomeric (S)-PMP series were synthesized by reactions of primary or secondary amines with 6-chloro-9-{[2-(diisopropoxyphosphoryl)methoxy]alkyl}purines (26-28) or 2-amino-6-chloro-9-{[2-(diisopropoxy- phosphoryl)methoxy]alkyl}purines (29-31) followed by treatment of the diester intermediates32with bromo(trimethyl)silane and hydrolysis. Diesters32were also obtained by reaction ofN6-substituted purines with synthons23-25bearing diisopropoxyphospho

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