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Journal articles on the topic 'Thieno'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Kulakov, Ivan, Mariya Matsukevich, Maxim Levin, Irina Palamarchuk, Tulegen Seilkhanov, and Alexander Fisyuk. "Synthesis of the First Representatives of Thieno[3,2-c][1,7]naphthyridine Derivatives Based on 3-Amino-6-methyl-4-(2-thienyl) pyridin-2(1H)-one." Synlett 29, no. 13 (2018): 1741–44. http://dx.doi.org/10.1055/s-0037-1610445.

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A one-pot method for obtaining novel thieno[3,2-c][1,7]naphthyridine derivatives based on the reaction of 3-amino-4-(thien-2-yl)pyridin-2(1H)-one with aromatic aldehydes in 80% phosphoric acid at 130 °C has been developed. The formation of the thieno[3,2-c][1,7]naphthyridine ring was due to the intermediate generation of the corresponding azomethine, which underwent intramolecular cyclization with electrophilic attack of the β-carbon atom of the thiophene core under Pictet–Spengler conditions. The isolated 5,7-dihydrothieno[3,2-c][1,7]naphthyridin-4(3H)-ones underwent oxidative aromatization

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2

Kut, M., D. Kut, and M. Onysko. "REGIOSELECTIVITY OF THE TELLURIUM-INDUCED CYCLISATION OF TERMINALLY SUBSTITUTED ALLYL, BUTENYL AND PROPARGYL THIOETHERS OF THIENOPYRIMIDINE." Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 48, no. 2 (2023): 54–60. http://dx.doi.org/10.24144/2414-0260.2022.2.54-60.

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The method of electrophilic intramolecular cyclization is widely used for the synthesis of condensed thienopyrimidine derivatives. In this work, the regioselectivity of the process of electrophilic intramolecular cyclization of terminally substituted allylic derivatives, but-1-enyl and propargyl thioethers of thienopyrimidine with p-methoxyphenyltellurttrichloride was investigated. It was established that as a result of the tellurium-induced cyclization of butenyl thioethers of 5,6-dimethyl-3-phenylthieno[2,3-d]pyrimidin-4(3H)-one with p-methoxyphenyltellurium trichloride, angular tricyc

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3

Obushak, Mykola D., Fedor I. Zubkov, Maryana A. Nadirova та ін. "Application of the Intramolecular Diels–Alder Vinylarenе (IMDAV) Approach for the Synthesis of Thieno[2,3-f]isoindoles". Synthesis 52, № 15 (2020): 2196–223. http://dx.doi.org/10.1055/s-0039-1690833.

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3-(Thien-2-yl)- and 3-(thien-3-yl)allylamines, readily accessible from the corresponding thienyl aldehydes, can interact with a broad range of anhydrides and α,β-unsaturated acids chlorides (maleic, сitraconic, and phenyl maleic anhydrides, сrotonyl and сinnamyl chlorides, etc.) leading to the formation of a thieno[2,3-f]isoindole core. Usually, the reaction sequence involves three successive steps: acylation of the nitrogen atom of the initial allylamine, the intramolecular Diels–Alder vinylarenе (IMDAV) reaction, and the final aromatization of the dihydrothiophene ring in the Diels–Alder ad

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4

Abhishek, S. Saxena, Goel Atul, and Ji Ram Vishnu. "A convenient and expwitious synthesis of annulated N, S-heterocycles." Journal of Indian Chemical Society Vol. 80, Apr 2003 (2003): 311–18. https://doi.org/10.5281/zenodo.5839578.

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Medicinal Chemistry Division, Central Drug Research ln$titute, Lucknow-226 001, India E-mail : vjiram@yahoo.com_ Fax: 91-522-223405 <em>Manuscript received 19 September 2002</em> A convenient synthesis of titiett[2,3-<em>b</em>]pyridines (3), thieno[3,2-<em>c</em>]pxridines (4), pyrazolo[3,4-<em>b</em>]ipyridines (6), thieno[2,3- <em>d</em>]pyrimidines (9), pyridoll,2-althienol2,3-dlpyrimidines (11), pyrido[1,2-<em>a</em>]pyrimido141,51 : 4,5[thien:o[2,3-<em>d</em>]pyrimidines (12), pyrido[1,2-<em>a</em>]pyrimido[4,5-<em>d</em>]pyiimidines (13) and pyrazolor[3,4-<em>d</em>]pyrimido[1,2-a]pyrim

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5

Irgashev, Roman A., Nadezhda S. Demina, Polina E. Bayankina, Nikita A. Kazin, and Gennady L. Rusinov. "An Effective Route to Dithieno[3,2-b:2′,3′-d]thiophene-Based Hexaheteroacenes." Synlett 32, no. 10 (2021): 1009–13. http://dx.doi.org/10.1055/a-1398-7237.

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AbstractA series of 12H-[1]benzo[4′′,5′′]thieno[2′′,3′′:4′,5′]thieno[2′,3′:4,5]thieno[3,2-b]indoles were efficiently prepared in three steps starting from available benzo[b]thieno[2,3-d]thiophen-3(2H)-ones. These fused ketones were treated with the Vilsmeier reagent and hydroxylamine hydrochloride to give the corresponding 3-chlorobenzo[b]thieno[2,3-d]thiophene-2-carbonitriles, which then reacted with methyl sulfanylacetate to form methyl 3-aminobenzo[4′,5′]thieno[2′,3′:4,5]thieno[3,2-b]thiophene-2-carboxylates, in accordance with the Fiesselmann thiophene synthesis protocol. Finally, the desi

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6

Stasevych, Maryna, Svitlana Sabat, Rostyslav Musyanovych, and Volodymyr Novikov. "Synthesis of condensed S-, N- containing heterocyclic systems on the base of 2-amino-4,9-dioxo-4,9-dihydronaphto[2,3-b]thiophene-3-ethylcarboxilate." Chemistry & Chemical Technology 2, no. 3 (2008): 157–62. http://dx.doi.org/10.23939/chcht02.03.157.

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Synthesis of a new 2-aryl-4Н-naphtho[2’,3’,4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones, 2-arylnaphtho[2’,3’,4,5]thieno[2,3-d][1,3]pyrimidine-4,5,10(3Н)-triones, 3-phenyl naphtho[2’,3’,4,5]thieno[2,3-d][1,3]pyrimidine-2,4,5,10(1Н, 3Н)-tetraone and 2-thioxo-2,3-dyhydronaphth[2’,3’,4,5]thieno[2,3-d]pyrimidine-4,5,10(1Н)-trione was carried out. The mechanism of 2-aryl-4Н-naphtho[2’,3’,4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones formation was suggested.

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7

Gronowitz, Salo, Johan Malm, and Anna-Britta Hörnfeldt. "Synthesis of the six isomeric thieno[c]-fused 1,5- and 1,6-naphthyridines." Collection of Czechoslovak Chemical Communications 56, no. 11 (1991): 2340–51. http://dx.doi.org/10.1135/cccc19912340.

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trough the use of Pd(0)-catalyzed coupling between 2- and 4-formyl-3-thiopheneboronic acids and 3-amino-2-bromopyridine and 4-acetamido-3-bromopyridine, convenient one-pot procedures for the preparation of thieno[2,3-c]-1,5-naphthyridine, thieno[3,4-c]-1,5-naphthyridine, thieno-[2,3-c]-1,6-naphthyridine, and thieno[3,4-c]-1,6-naphthyridine have been developed. In order to obtain thieno[3,2-c]-1,6-naphthyridine 2-(tributylstannyl)-3-thiophene aldehyde had to be used, since the organometallic partner in the coupling reaction, 3-formyl-2-thipheneboronic acid, is too easily deboronated. The effect

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8

Elgogary, Sameh R., Emad M. El-Telbani, and Ibrahim Radini. "Syntheses and Biological Activities of Tricyclic-fused Quinoxaline Ring Systems (A Review). Part I: Thienoquinoxalines." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 34, no. 02 (2024): 173. http://dx.doi.org/10.59467/ijhc.2024.34.173.

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Quinoxaline derivatives are an interesting class of heterocyclic compounds in drug discovery. It is rare in natural state, but their synthesis is easy to perform coupling between benzene and pyrazine rings. In addition, quinoxaline nucleus has received notable attention as an important pharmacophore that has broad-spectrum applications, especially in the fields of pharmaceutics and medicine. This review spotlights the biological activities and the different methods of preparation of three isomers of thienoquinoxalines, namely thieno[2,3-b]quinoxaline, thieno[3,4-b]quinoxaline, and thieno[2,3-g

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9

Nguyen, Hien, Ngan Nguyen Bich, Tung T. Dang, and Luc Van Meervelt. "Stacking patterns of thieno[3,2-b]thiophenes functionalized by sequential palladium-catalyzed Suzuki and Heck cross-coupling reactions." Acta Crystallographica Section C Structural Chemistry 70, no. 9 (2014): 895–99. http://dx.doi.org/10.1107/s2053229614018683.

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The crystal structures of three 5-alkenyl-2-arylthieno[3,2-b]thiophenes, namely 3,6-dibromo-5-(4-tert-butylstyryl)-2-(naphthalen-1-yl)thieno[3,2-b]thiophene, C28H22Br2S2, (I), 3,6-dibromo-5-(4-methylstyryl)-2-(naphthalen-1-yl)thieno[3,2-b]thiophene, C25H16Br2S2, (II), and 3,6-dibromo-2-(4-tert-butylphenyl)-5-(4-methylstyryl)thieno[3,2-b]thiophene, C25H22Br2S2, (III), have been determined in order to evaluate the geometry of the molecules. The π-conjugated system containing the thieno[3,2-b]thiophene skeleton, the ethylene bridge and the phenyl rings is almost planar. The aromatic ring directly

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10

Bremner, John B., and Zemin Wu. "Annulation of Eight- to Ten-Membered Oxaza Rings to the Benzo[b]thiophene System by Intramolecular Nucleophilic Displacement." Australian Journal of Chemistry 67, no. 9 (2014): 1217. http://dx.doi.org/10.1071/ch14055.

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Concise synthetic routes to 2H-benzo[b]thieno[3,2-b][1,5]oxazocin-6(3H)-one, and the new benzo[b]thieno[3,2-b][1,5]oxazonin-7(2H)-one and 2H-benzo[b]thieno[3,2-b][1,5]oxazecin-8(3H)-one systems, have been developed based on intramolecular nucleophilic displacement in the key ring forming step.

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11

Mohareb, Rafat M., Sherif M. Sherif, Adiba Habashi, Nadia I. Abdel-Sayed, and Samia S. Osman. "Reaction of Carbon Disulfide with Active Methylenes: Novel Synthesis of Thiophene, Thieno[2,3-b]thiophene, Thieno[3,2-c]pyrazole and Thieno[3,2-b]pyridine Derivatives." Collection of Czechoslovak Chemical Communications 60, no. 9 (1995): 1578–86. http://dx.doi.org/10.1135/cccc19951578.

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The active methylene compounds - derivatives of malonic or 4-oxobutanoic acid - reacted with carbon disulfide in dimethyl formamide containing potassium hydroxide to yield the non-isolable dipotassium disulfide intermediates. The latter were cyclized by α-haloketones to give thiophene, thieno[2,3-b]thiophene, thieno[3,2-c]pyrazole and thieno[3,2-b]pyridine derivatives. The reactivity of the products toward various reagents was studied.

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12

Lewinska, Gabriela, Jerzy Sanetra, Konstanty W. Marszalek, Alexander Quandt, and Bouchta Sahraoui. "Influence of Temperature on the Optical Properties of Ternary Organic Thin Films for Photovoltaics." Materials 18, no. 14 (2025): 3319. https://doi.org/10.3390/ma18143319.

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This study investigates the influence of temperature on the linear and nonlinear optical properties of ternary organic thin films for solar cell applications. Three-component organic thin films (poly({4,8-bis[(2-ethylhexyl)oxy]benzo [1,2-b:4,5-b′]dithiophene-2,6-diyl}{3-fluoro-2-[(2-ethylhexyl)carbonyl] thieno[3,4-b]thiophenediyl}) and (poly([2,6′-4,8-di(5-ethylhexylthienyl)benzo[1,2-b;3,3-b]dithiophene]{3-fluoro-2[(2-ethylhexyl)carbonyl]thieno[3,4-b]thiophenediyl}), marked PTB7 and PTB7th- donors, PCBM, phenyl-C61-butyric acid methyl ester acceptor, and Y5: 2,2′-((2Z,2′Z)-((12,13-bis(2-ethylh

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13

Demina, Nadezhda S., Nikita A. Kazin, Nikolay A. Rasputin, Roman A. Irgashev, and Gennady L. Rusinov. "Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction." Beilstein Journal of Organic Chemistry 15 (November 12, 2019): 2678–83. http://dx.doi.org/10.3762/bjoc.15.261.

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Fiesselmann thiophene synthesis was applied for the convenient construction of thieno[3,2-b]thiophene derivatives. Thus, new 5- or 6-aryl-3-hydroxythieno[3,2-b]thiophene-2-carboxylates were obtained by condensation of 5- or 4-aryl-3-chlorothiophene-2-carboxylates, respectively, with methyl thioglycolate in the presence of potassium tert-butoxide. The saponification of the resulting esters, with decarboxylation of the intermediating acids, gave the corresponding thieno[3,2-b]thiophen-3(2H)-ones. The latter ketones were used to synthesize new N,S-heterotetracenes, namely 9H-thieno[2',3':4,5]thie

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14

Hafez, Hend N., and Abdel-Rhman B. A. El-Gazzar. "Synthesis and evaluation of antitumor activity of new 4-substituted thieno[3,2-d]pyrimidine and thienotriazolopyrimidine derivatives." Acta Pharmaceutica 67, no. 4 (2017): 527–42. http://dx.doi.org/10.1515/acph-2017-0039.

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Abstract 3-Methyl-6-phenyl-2-thioxo-2,3-dihydrothieno[3,2-d]pyrimidin- 4(1H)-one (2), on treatment with phosphorous oxychoride, affored 4-chloro-3-methyl-6-phenyl -thieno[3,2-d]pyrimidine- 2(3H)-thione (3). A series of novel 6-phenyl-thieno[3,2-d]pyrimidine derivatives 4-9 bearing different functional groups were synthesized via treatment of compound 3 with different reagents. On the other hand, compound 2 was used to synthesize ethyl-[(3-methyl-6-phenyl-2-thioxo-2,3-dihydrothieno[ 3,2-d]pyrimidin-4-yl)-oxy]acetate (10), 2-hydrazinyl- -3-methyl-6-phenyl-thieno[3,2-d]pyrimidin-4(3H)-one (11), 3

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15

Ahmed, Essam K., Johannes Fröhlich, and Fritz Sauter. "Fusion Reactions of N-Heterocyclic Moieties to Thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidines." Collection of Czechoslovak Chemical Communications 61, no. 1 (1996): 147–54. http://dx.doi.org/10.1135/cccc19960147.

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Derivatives of the novel heterocyclic parent systems imidazolo[1,2-a]thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidine (B) and thiopyrano[4',3':4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (C) have been synthesized by fusing pyrimidine moieties to 2-amino-4,7-dihydro-5H-thieno[2,3-c]thiopyran-3-carboxylic acid ethyl ester (1) and -3-carbonitrile (10), followed by cyclization reactions of the title intermediates A thus obtained.

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16

Prasad, M. Raghu, A. Raghuram Rao, P. Shanthan Rao, and K. Subramanian Rajan. "A Facile Route for the Synthesis of Thienopyrimidines." Journal of Chemical Research 2002, no. 1 (2002): 5–6. http://dx.doi.org/10.3184/030823402103170439.

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17

Hamed, Atef A., Hesham F. Bader, and El-Sayed H. El-Ashry. "4′, x-Seco And 4′,x-4′,5′-Diseco C-Nucleosides From 2-Hydrazino-(3H)- Thieno [2,3-D] Pyrimidin-4-Ones." Zeitschrift für Naturforschung B 56, no. 8 (2001): 826–36. http://dx.doi.org/10.1515/znb-2001-0817.

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Cyclization of 2-hydrazino-5,6-dimethyl-3H-thieno[2,3-d]pyrimidin-4-one (1) with acetic acid gave 3,6,7-trimethyl-l,2,4-triazolo[3,4-a]thieno[2,3-d] pyrimidin-5-one (5) whose Dimroth rearrangement gave 2,6,7-trimethyl-l,2,4-triazolo[3,4-a]thieno[2,3-d]pyrimidin-5-one (11). Alternatively, 5 was obtained from the dehydrogenative cyclization of acetaldehyde 5,6- dimethyl-4-3H-oxo-thieno[2,3-d]pyrimidin-2-yl hydrazone (7). Reaction of 1 and 2 with a number of sugars gave the respective hydrazones 19 and 20. Those of the D-glucose exist in the cyclic pyranosyl structure in addition to minor amounts

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18

Bin Chen, Bin Chen, Han Zhang, Wenwen Luo, et al. "Oxidation-enhanced emission: exploring novel AIEgens from thieno[3,2-b]thiophene S,S-dioxide." Journal of Materials Chemistry C 5, no. 4 (2017): 960–68. http://dx.doi.org/10.1039/c6tc05116b.

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19

Kaliendina, S., M. Brynzei, M. Kut, S. M. Sukharev, Е. Ostapchuk та M. Onysko. "Kaliendina S., Brynzei M., Kut M., Sukharev S.M., Ostapchuk Е., Onysko M. REGIOSELECTIVITY OF ALKYLATION OF 2-(THIOPHENE-2-IL)THIENO[2,3 d]PYRIMIDINE-4(3H)-ONE". Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 50, № 2 (2024): 40–45. http://dx.doi.org/10.24144/2414-0260.2023.2.40-45.

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Thieno[2,3-d]pyrimidines are an important class of heterocyclic compounds with a wide range of biological activities. The thieno[2,3-d]pyrimidin-4-one system is of the greatest interest to scientists, as it is one of a large number of possible thienopyrimidine derivatives. The presence of an amide fragment in these molecules allows for the introduction of various substituents via alkylation reactions. On the other hand, the presence of N- and O-nucleophilic centres makes it possible to form different types of alkylation products. In the present work, the alkylation reaction of 5,6-dimeth

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20

Zhang, Xin, Yunqian Ding, Xiangjian Wan, Xin Ke, Chenxi Li, and Yongsheng Chen. "A novel acceptor with a N,N-dialkyl thieno[3′,2′:2,3]indolo[7,6-g]thieno[3,2-b]indole (TITI) core for organic solar cells with a high fill factor of 0.75." Chemical Communications 56, no. 5 (2020): 751–53. http://dx.doi.org/10.1039/c9cc08098h.

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21

Ibrahim, Yehia A., and Balkis Al-Saleh. "Synthetic Approaches towards [1]Benzopyrano [4,3-b]Thieno[2,3-e]Pyridines via Intramolecular Diels-Alder Reactions of 1,2,4-Triazines." Journal of Chemical Research 2002, no. 2 (2002): 60–61. http://dx.doi.org/10.3184/030823402103171212.

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Efficient syntheses are reported of [1]benzopyrano[4,3-b]thieno[2,3-e]pyridines (20), by the application of an intramolecular Diels–Alder reaction employing the intermediate appropriately designed functionalised thieno [3,2-e][1,2,4]triazines.

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22

Ibrahim, Yehia A., and Balkis Al-Saleh. "Synthetic Approaches towards [1]Benzopyrano [4,3-b]Thieno[2,3-e]Pyridines via Intramolecular Diels-Alder Reactions of 1,2,4-Triazines." Journal of Chemical Research 2002, no. 2 (2002): 60–61. http://dx.doi.org/10.3184/030823402103171267.

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Efficient syntheses are reported of [1]benzopyrano[4,3-b]thieno[2,3-e]pyridines (20), by the application of an intramolecular Diels–Alder reaction employing the intermediate appropriately designed functionalised thieno [3,2-e][1,2,4]triazines.

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23

Sonawane, Amol D., Dinesh R. Garud, Taro Udagawa, Yasuhiro Kubota, and Mamoru Koketsu. "Synthesis of thieno[2,3-c]acridine and furo[2,3-c]acridine derivatives via an iodocyclization reaction and their fluorescence properties and DFT mechanistic studies." New Journal of Chemistry 42, no. 18 (2018): 15315–24. http://dx.doi.org/10.1039/c8nj03511c.

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In this paper, we report the novel synthesis of thieno[2,3-c]acridine and furo[2,3-c]acridine derivatives via intramolecular iodocyclization reaction. The thieno[2,3-c]acridine derivatives exhibited blue fluorescence in hexane.

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24

Yin, Xuelian, Sung Min Kim, and Yang-Heon Song. "1,3-Bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)imidazolidine-4,5-dione." Molbank 2022, no. 3 (2022): M1403. http://dx.doi.org/10.3390/m1403.

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A thieno[2,3-d]pyrimidine derivative 3 bearing a 4,5-imidazolidinedione moiety, 1,3-bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)imidazolidine-4,5-dione, was efficiently synthesized in 66% yield by the reaction of N,N′-bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)methanediamine 2 with oxalyl chloride in the presence of pyridine in refluxing dichloroethane for 10 h. The structure of the new synthesized compounds was fully characterized by 1H, 13C NMR, IR spectroscopy, mass-spectrometry and elemental analysis.

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25

El-Dean, Adel M. Kamal, Shaban M. Radwan, and Yasser A. Elosealy. "Synthesis of some new imidazo[3″,4″:1′,2′] pyrimido[4′,5′:4,5]thieno[2,3-c] pyridazines and other fused thieno[2,3-c]pyridazines." Journal of Chemical Research 2008, no. 11 (2008): 622–25. http://dx.doi.org/10.3184/030823408x371056.

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5-Amino-3,4-diphenylthieno[2,3-c]pyridazine-6-carboxamide was prepared and used as starting material to form the novel 6-chloromethyl-3,4-diphenylpyrimido[4′,5′:4,5]thieno[2,3-c]pyridazin-8(7H)-one (3), the 6-(arylaminomethyl) compounds (4a–c), 7-aryl-7,8-dihydro-3,4-diphenylimidazo[3″,4″:1′,2′]pyrimido[4′,5′:4,5]thieno[2,3-c]pyridazin-10(6H)-ones (5a–c), ethyl 7,8-dihydro-8-oxopyrimido[4′,5′:4,5]thieno[2,3-c]pyridazine-6-acetate (6) and its carbohydrazide (7). The pyridazinothienopyrimidotriazepinedione 8, pyridothienopyridazine 12 and pyridazinothienooxazepine 13 were also prepared.

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26

Yu, Huchang, Yan Li, Zhiyuan Feng, et al. "Synthesis, Crystal Structure and Antitumour Activity Evaluation of 1H-thieno[2,3-c]chromen-4(2H)-one Derivatives." Journal of Chemical Research 41, no. 1 (2017): 36–41. http://dx.doi.org/10.3184/174751917x14837116219573.

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A series of 1 H-thieno[2,3-c]chromen-4(2 H)-one derivatives were synthesised through Knoevenagel condensation of substituted flavanones with thiazolidine-2,4-dione in ethanol in the presence of piperidine. The mechanism of the reaction was proposed. All synthesised compounds were characterised by IR, 1H NMR, 13C NMR, HRMS, and elemental analysis. The structure of 2-(3-chlorophenyl)-1 H-thieno[2,3- c]chromen-4(2 H)-one was confirmed by a single crystal X-ray diffraction analysis. A preliminary antitumour screening showed that 2-(2-fluorophenyl)-1 H-thieno [2,3- c]chromen-4(2 H)-one had moderate

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27

Chao, Ying-Chieh, Jhe-Han Chen, Yi-Jie Chiou, et al. "Design of Thienothiophene-Based Copolymers with Various Side Chain-End Groups for Efficient Polymer Solar Cells." Polymers 12, no. 12 (2020): 2964. http://dx.doi.org/10.3390/polym12122964.

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Three two-dimensional donor–acceptor conjugated copolymers consisting of a benzo[1,2-b:4,5-b′]dithiophene derivative and thieno[3,2-b]thiophene with a conjugated side chain were designed and synthesized for use in bulk heterojunction (BHJ) or nonfullerene polymer solar cells (PSCs). Through attaching various acceptor end groups to the conjugated side chain on the thieno[3,2-b]thiophene moiety, the electronic, photophysical, and morphological properties of these copolymers were significantly affected. It was found that the intermolecular charge transfer interactions were enhanced with the incre

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Zhou, Yue, Jie Hao, and Dongbing Zhao. "Divergent synthesis of 3-substituted thieno[3,4-b]thiophene derivatives via hydroxy-based transformations." Materials Chemistry Frontiers 3, no. 7 (2019): 1422–26. http://dx.doi.org/10.1039/c9qm00128j.

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Modular assembly of 3-substituted thieno[3,4-b]thiophenes: we have developed the first Pd-catalytic method to access 3-hydroxythieno[3,4-b]thiophene-2-carboxylate, which can be widely utilized for modular assembly of structurally diverse 3-substituted thieno[3,4-b]thiophene derivatives.

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Kut, D., M. M. Kut, and R. T. Mariychuk. "SYNTHESIS OF N-ALKENYL(ALKYNYL)-5,6-DIMETHYL-2-(THIOPHEN-2-YL)THIENO[2,3-d]PYRIMIDIN-4-AMINES AND THEIR IN SILICO STUDY ON GROUP II CHITINASE (ChtII) INHIBITION." Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 52, no. 2 (2024): 75–82. https://doi.org/10.24144/2414-0260.2024.2.75-82.

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Research in the chemistry of heterocyclic compounds, particularly condensed pyrimidine frameworks, aimed at developing drugs with diverse therapeutic properties. Among these compounds, special attention is given to thieno[2,3-d]pyrimidine derivatives due to their potential as drug candidates. This study presents the synthesis of a series of N-alkenyl(alkynyl)-5,6-dimethyl-2-(thiophen-2-yl)-thieno[2,3-d]pyrimidin-4-amines via the amination reaction of 5,6-dimethyl-2-(thiophen-2-yl)-4-chlorothieno[2,3-d]pyrimidine with unsaturated amines (allyl-, diallyl-, and propargylamine), enabling potential

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30

Nie, Li Fei, Guozheng Huang, Khurshed Bozorov, et al. "Diversity-oriented synthesis of amide derivatives of tricyclic thieno[2,3-d]pyrimidin-4(3H)-ones and evaluation of their influence on melanin synthesis in murine B16 cells." Heterocyclic Communications 24, no. 1 (2018): 43–50. http://dx.doi.org/10.1515/hc-2017-0256.

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Abstract A diversity-oriented synthesis of amide-containing thieno[2,3-d]pyrimidin-4(3H)-ones is reported. All compounds were tested for their influence on melanin synthesis in murine B16 cells. The azepine fragment in thieno[2,3-d]pyrimidin-4(3H)-one skeleton significantly increases the melanin content.

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31

Haverkate, Natalie A., Euphemia Leung, Lisa I. Pilkington, and David Barker. "Disruption of Crystal Packing in Thieno[2,3-b]pyridines Improves Anti-Proliferative Activity." Molecules 27, no. 3 (2022): 836. http://dx.doi.org/10.3390/molecules27030836.

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3-Amino-2-arylcarboxamido-thieno[2,3-b]pyridines have been shown to have anti-proliferative activity, but are also known to have poor solubility. This has been previously proposed to be due to their extensive planarity, which allows for intermolecular stacking and crystal packing. We herein report the synthesis of fifteen novel thieno[2,3-b]pyridines that have incorporated bulky, but easily cleavable, ester and carbonate functional groups in an effort to decrease crystal packing. The addition of these ‘prodrug-like’ moieties into the thieno[2,3-b]pyridine resulted in compounds with increased a

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32

Yin, Xuelian, and Yang-Heon Song. "5-Methyl-1-phenyl-3-(thieno[2,3-d]pyrimidin-4-yl)chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one." Molbank 2022, no. 4 (2022): M1469. http://dx.doi.org/10.3390/m1469.

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A chromeno[4,3-d]pyrazolo[3,4-b]pyridinone derivative 3 bearing thieno[2,3-d]pyrimidine moiety, 5-methyl-1-phenyl-3-(thieno[2,3-d]pyrimidin-4-yl)chromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one, was efficiently prepared in 75% yield by the reaction of 3-phenyl-1-(thieno[2,3-d]pyrimidin-4-yl)-1H-pyrazol-5-amine 1 with 3-acetyl-2H-chromen-2-one 2 in the presence of FeCl3-SiO2 as a catalyst in refluxing ethanol for 6 h. The structure of the new synthesized compound was characterized by 1H-, 13C- NMR, IR spectroscopy, mass-spectrometry, and elemental analysis.

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33

Liu, Feize, Xueling Hou, Li Nie, Khurshed Bozorov, Michael Decker, and Guozheng Huang. "A Convenient One-pot Synthesis of 2,3-Disubstituted Thieno[2,3-d]pyrimidin-4(3H)-ones from 2H-Thieno[2,3-d][1,3]oxazine-2,4(1H)-diones, Aromatic Aldehydes and Amines." SynOpen 02, no. 02 (2018): 0207–12. http://dx.doi.org/10.1055/s-0037-1610157.

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An efficient, simple protocol has been established for convenient synthesis of novel 2,3-disubstituted thieno[2,3-d]pyrimidin-4(3H)-one derivatives in good to high yields through a one-pot, two-step and three-component reaction from 2H-thieno[2,3-d][1,3]oxazine-2,4(1H)-diones, aromatic aldehydes, and amines.

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34

Singh, Shiv Dev, Arvind Kumar, Firoz Babar, Neetu Sachan, and Arun Kumar Sharma. "Synthesis of Novel 3(N,N-dialkylamino)alkyl/phenyl Substituted Thieno [2,3-d]pyrimidinones as H1-Anti-Histaminic and Antimicrobial Agents." Current Bioactive Compounds 15, no. 1 (2019): 63–70. http://dx.doi.org/10.2174/1573407214666180226130957.

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Background: Thienopyrimidines are the bioisoster of quinazoline and unlike quinazoline exist in three isomeric forms corresponding to the three possible types annulation of thiophene to the pyrimidine ring viz thieno[2,3-d] pyrimidine, thieno[3,2-d] pyrimidine and thieno[3,4-d]pyrimidine. Heterocyclic containing the thienopyrimidinone moiety exhibits various pronounced activities such as anti-hypertensive, analgesic and anti-inflammatory, antiviral, platelet aggregation inhibitory, antiprotozoal bronchodilatory, phosphodiesterase inhibitory, antihistaminic, antipsychotic and antimicrobial acti

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35

Hafez, Hend N., Abdel-Rhman B. A. El-Gazzar, and Magdi E. A. Zaki. "Simple approach to thieno[3,2-d]pyrimidines as new scaffolds of antimicrobial activities." Acta Pharmaceutica 66, no. 3 (2016): 331–51. http://dx.doi.org/10.1515/acph-2016-0029.

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Abstract 6ʹ-(4-Chlorophenyl)-spiro[cyclohexane-1,2ʹ-thieno[3,2-d][1,3] oxazin]-4ʹ(1ʹH)-one (1) was synthesized and used as a starting material for the synthesis of a novel series of spiro compounds having biologically active sulfonamide 2a-e and 3ʹ-(4-acetylphenyl)-6ʹ- (4-chlorophenyl)-1ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d] pyrimidine-4ʹ(3ʹH)-one (3). Compound 2a was used as a key intermediate for the synthesis of sulfonyl carbothioamide derivatives 4a-c. Also, compound 3 was used as an intermediate for the synthesis of 3ʹH-spiro[cyclohexane-1,2ʹ-thieno[3,2-d]pyrimidin]-3ʹ-yl] phenyl}-2-imin

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36

Bakhite, E. A., A. E. Abdel-Rahman, O. S. Mohamed, and E. A. Thabet. "synthesis of Some New Pyridothienopyrimidines and Related [1,2,4]Triazolopyridothienopyrimidines." Journal of Chemical Research 2003, no. 2 (2003): 58–59. http://dx.doi.org/10.3184/030823403103173156.

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4-Chloro-9-phenyl-7-(2-thienyl)pyrido[3′,2′:4,5]thieno[3,2- d]pyrimidine (5) and 3-amino-3,4-dihydro-4-imino-9-phenyl-7-(2-thienyl)pyrido[3′,2′:4,5]thieno[3,2- d]pyrimidine (19) were prepared and employed as precursors for synthesizing the fused-ring compounds of the title.

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Kanawade, Shrikant B., Shivaraj P. Patil, Prashant S. Nikam, Sachin A. Gangurde, Madhukar N. Jachak, and Raghunath B. Toche. "Synthesis of new thieno[2,3-d]pyrimidines, thieno[3,2-e]pyridines, and thieno[2,3-d][1,3]oxazines." Journal of Heterocyclic Chemistry 49, no. 2 (2011): 363–69. http://dx.doi.org/10.1002/jhet.748.

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38

Ma, Lanchao, Bing Chen, Yunlong Guo, et al. "NIR polymers and phototransistors." Journal of Materials Chemistry C 6, no. 47 (2018): 13049–58. http://dx.doi.org/10.1039/c8tc03917h.

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A novel bisthiophene-fused diketopyrrolopyrrole unit (4,11-bis(2-octyldodecyl)-7H,14H-thieno[3′,2′:7,8]indolizino[2,1-a]thieno[3,2-g]indolizine-7,14-dione, BTI) has been designed as an electron acceptor and used to copolymerize with thiophene and bithiophene as electron donors to construct two D–A conjugated polymers, P1 and P2via Stille coupling, respectively.

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39

Xie, Jian-Wu, Li-Si-Han Yu, Jian-Lian Dong, Zhi-Jian Gao, and Jing Wang. "Construction of Functionalized (Dihydro)thieno[2,3-c]chromene Derivatives via a Domino Michael Addition/Intramolecular Cyclization Reaction." Synthesis 50, no. 08 (2018): 1667–74. http://dx.doi.org/10.1055/s-0036-1591758.

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A one-pot synthesis of substituted (dihydro)thieno[2,3-c]chromene derivatives was developed through a Lewis base catalyzed domino Michael addition/intramolecular cyclization reaction between 3-nitro-2H-chromenes and thioamides. The desired (dihydro)thieno[2,3-c]chromene derivatives were prepared with a large substrate scope (22 examples) and excellent diastereoselectivity in moderate to excellent yields.

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40

Lagardère, Prisca, Cyril Fersing, Nicolas Masurier, and Vincent Lisowski. "Thienopyrimidine: A Promising Scaffold to Access Anti-Infective Agents." Pharmaceuticals 15, no. 1 (2021): 35. http://dx.doi.org/10.3390/ph15010035.

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Thienopyrimidines are widely represented in the literature, mainly due to their structural relationship with purine base such as adenine and guanine. This current review presents three isomers—thieno[2,3-d]pyrimidines, thieno[3,2-d]pyrimidines and thieno[3,4-d]pyrimidines—and their anti-infective properties. Broad-spectrum thienopyrimidines with biological properties such as antibacterial, antifungal, antiparasitic and antiviral inspired us to analyze and compile their structure–activity relationship (SAR) and classify their synthetic pathways. This review explains the main access route to syn

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41

Browne, EJ. "Synthesis of Benzo[D]Thieno[2,3-G]Azecine and Benzo[D][1]Benzothieno[2,3-G]Azecine Derivatives." Australian Journal of Chemistry 39, no. 5 (1986): 783. http://dx.doi.org/10.1071/ch9860783.

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Derivatives of two new diannulated azecine systems have been prepared by ring degradation of precursor bases with cyanogen -bromide-induced solvolysis. Reaction of a tetrahydro-5H-benzo[h] thieno [2,3,-a] quinolizine (5a) and a tetrahydro-7H-benzo[h][1] benzothieno [2,3-a] quinolizine (5b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded derivatives of a hexahydrobenzo [d] thieno [2,3-g] azecine (6a) and a hexahydrobenzo [d][1] benzothieno [2,3-g] azecine (6b), respectively. Functional group interconversions of these medium-ring systems were performed, including ox

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42

Halverson, Aileen Pfleider, Lyle W. Castle, and Raymond N. Castle. "Synthesis of two novel ring systemsviaphotocyclization: Thieno[2′,3′:4,5]thieno[2,3-c][1,10]phenanthroline and thieno[3′,2′:4,5]thieno[2,3-c][1,10]phenanthroline." Journal of Heterocyclic Chemistry 33, no. 1 (1996): 119–22. http://dx.doi.org/10.1002/jhet.5570330121.

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43

Rizak, Galina. "SEARCH FOR BİOLOGİCALLY ACTİVE SUBSTANCES USİNG THE EXAMPLE OF 2.4-DIOXO- AND 4-IMINO-2-OXO- 3-PHENYL-5-R-6-R`-THIENO[2.3-D]PYRIMIDINES, ROSPECTS FOR THEİR USE İN PHARMACY AND MEDİCİNE." Azerbaijan Pharmaceutical and Pharmacoterapy Journal 23, no. 1 (2023): 29–46. http://dx.doi.org/10.58495/bucc4973.

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The purpose of this paper was the development of new bioactive substances – derivatives of 2.4-dioxo- and 4-imino-2-oxo-3-phenyl-5-R-6-R`-thieno[2.3-d]pyrimidines; researching the structure of invented substances and conducting their pharmacological analysis. Such research methods were used as synthesis of ethyl 4-R-5-R`-2-aminothiophene-3-carboxylates, nitriles of 4- R-5-R`-2-aminothiophene-3-carboxylic acids, their ureide derivatives 2.4-dioxo- and 4-imino-2- oxo-3-phenyl-5-R-6-R`-thieno[2.3-d]pyrimidines, their alkyl, acyl and cyanoethyl derivatives and products of their chemical transforma

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44

Ketova, Elena S., Anna V. Myazina, Elena Yu Bibik, Sergey G. Krivokolysko, Galina A. Batishcheva, and Victoria V. Shishkina. "WEIGHT ASSESSMENT OF RATS AFTER PROLONGED HIGH-FAT AND STEROID LOAD WITH PHARMACOCORRECTION WITH ORIGINAL THIENO[2,3-B]QUINOLINE AND 1,4-DIHYDROPYRIDINE DERIVATIVES." Bulletin of Medical Science 31, no. 3 (2023): 86–93. http://dx.doi.org/10.31684/25418475-2023-3-86.

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Introduction. Currently, the problem of effective and safe pharmacological correction of alimentary obesity and its concomitant conditions is of particular relevance. New derivatives of thieno[2,3-b]quinoline and 1,4-dihydropyridine are promising in this direction, stimulating their study in silico and in vivo. Research aim: In vivo study of the effect of new derivatives of thieno[2,3-b]quinoline and 1,4-dihydropyridine on the weight dynamics of adult Wistar rats after modeling alimentary obesity and metabolic disorders. Methods Three samples of thieno[2,3-b]quinoline and 1,4-dihydropyridine d

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45

Tsuchiya, Takashi, Shuji Yasuike, and Jyoji Kurita. "Syntheses of Novel Group 15 and 16 Thieno[2,3-b]-, Thieno[3,4-b]-, and Thieno[3,2-b]-heteroles." HETEROCYCLES 45, no. 10 (1997): 1891. http://dx.doi.org/10.3987/com-97-7911.

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46

Jarak, Ivana, Marijeta Kralj, Ivo Piantanida, et al. "Novel cyano- and amidino-substituted derivatives of thieno[2,3-b]- and thieno[3,2-b]thiophene-2-carboxanilides and thieno[3′,2′:4,5]thieno- and thieno[2′,3′:4,5]thieno [2,3-c]quinolones: Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation." Bioorganic & Medicinal Chemistry 14, no. 8 (2006): 2859–68. http://dx.doi.org/10.1016/j.bmc.2005.12.004.

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47

El-Dean, Adel M. Kamal, Gehan Ahmed Ali Micky, Abo Bakr Abdel-Hadi Ahmed, and Rasha Hassan Ahmed. "Convenient synthesis and reactions of some 7,9-dimethylthieno-[2,3-b:4,5-b‘]dipyridines." Journal of Chemical Research 2009, no. 10 (2009): 649–52. http://dx.doi.org/10.3184/030823409x12532880131016.

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3-Amino-4,6-dimethylthieno[2,3- b]pyridine-2-carboxaldehyde was prepared and from it various functionalised thieno[2,3- b:4,5- b‘]dipyridines were synthesised, using the Friedländer and related reactions. Ethyl 2,7,9-trimethylthieno[2,3- b:4,5- b‘]dipyridine-3-carboxylate was transformed into a variety of thieno[2,3- b:4,5- b‘]dipyridine systems with heterocyclic rings attached at C-3 or fused at C2–C3.

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48

Gomha, Sobhi, Ikhlass Abbas, Mohamed Elneairy, Mahmoud Elaasser, and Bazada Mabrouk. "Antimicrobial and anticancer evaluation of a novel synthetic tetracyclic system obtained by Dimroth rearrangement." Journal of the Serbian Chemical Society 80, no. 10 (2015): 1251–64. http://dx.doi.org/10.2298/jsc141222022g.

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A series of pyrido[3',2':4,5]thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidines were prepared via oxidative cyclization of 4-(2-arylidenehydrazinyl)pyrido [3',2':4,5]thieno[3,2-d] pyrimidines. Dimroth rearrangement of such a series yielded pyrido[3',2':4,5]thieno[2,3-e][1,2,4]triazolo[1,5-c]pyrimidines. The reaction mechanism was proposed and the products were screened for their antimicrobial and anticancer activities. From the antimicrobial screening results, it can be seen that compounds 8c, 9f and 10c showed excellent activity against gram positive bacteria while compounds 10d and 8c showed the

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49

Kim, Seongyun, Soomin Ryu, Jihae Ahn, et al. "Solution-Processable Benzo[b]thieno[2,3-d]thiophene Derivatives as Organic Semiconductors for Organic Thin-Film Transistors." Coatings 13, no. 8 (2023): 1417. http://dx.doi.org/10.3390/coatings13081417.

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Two new benzo[b]thieno[2,3-d]thiophene (BTT) derivatives, 2-(benzo[b]thiophen-5-yl)benzo[b]thieno[2,3-d]thiophene (compound 2), and 2-(benzo[b]thieno[2,3-d]thiophene-2yl)dibenzo[b,d]thiophene (compound 3) have been synthesized and utilized as solution-processable small molecular organic semiconductors for organic field-effect transistors (OFETs). The physicochemical characteristics of the recently created substances were analyzed using thermogravimetric analysis (TGA), differential scanning calorimeter (DSC), and UV-vis spectroscopy. Subsequently, the above-mentioned substances were employed a

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50

Gewald, K., S. Rennert, R. Schindler, and H. Sch�fer. "Amino-thieno[2,3-c]pyrazole und Amino-thieno[2,3-b]pyrrole." Journal f�r Praktische Chemie/Chemiker-Zeitung 337, no. 1 (1995): 472–77. http://dx.doi.org/10.1002/prac.199533701101.

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