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Journal articles on the topic 'Fused imidazoles'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Aly, Ashraf A. "Base Catalyzed Synthesis of Novel Fused-Imidazoles from N-Vinyl-1H-imidazole." Zeitschrift für Naturforschung B 60, no. 1 (2005): 106–12. http://dx.doi.org/10.1515/znb-2005-0116.

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Syntheses of various classes of fused-imidazoles are reported. The key to their successful synthesis depends on the reaction of N-vinyl-1H-imidazole with the π-deficient compounds under basic conditions. Reaction of the target imidazole with 1,1,2,2-tetracyanoethylene and dimethyl acetylenedicarboxylate afforded pyrrolo[1,2-a]imidazoles. On the other site, reaction of the target imidazole with 2-dicyanomethyleneindane-1,3-dione, 2,3-dicyano-1,4-naphthoquinone gave indanylimidazolo- [1,2-a]azepine and imidazolo[2,1-a]phenanthridine derivatives, respectively. Under basic reaction condition, vari

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2

Frippiat, Steven, Christine Baudequin, Christophe Hoarau, et al. "Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles." Synlett 31, no. 10 (2020): 1015–21. http://dx.doi.org/10.1055/s-0040-1708003.

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The palladium-catalyzed arylation and alkenylation of N-substituted methyl imidazole-4-carboxylates are described through inter- and intramolecular pathways. Both direct C2–H and C5–H arylation and alkenylation proceed under Pd(0)/Cu(I) cooperative catalysis and Pd(0) catalysis, respectively, in low-polarity 1,4-dioxane solvent. The methodology gives access to C2 (hetero)aryl or alkenyl imidazoles as well as innovative C2- and C5-arylated fused imidazoles tricycles with a five- to seven-membered middle ring.

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3

Kwak, Jung Pyo, Pham Duy Quang Dao, Nam Sik Yoon, and Chan Sik Cho. "Microwave-assisted green construction of imidazole-fused hybrid scaffolds using 2-aminobenzimidazoles as building blocks." RSC Advances 11, no. 35 (2021): 21367–74. http://dx.doi.org/10.1039/d1ra04396j.

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A green synthesis of trinuclear imidazole-fused hybrid scaffolds has been developed by transition metal-free double C(sp<sup>2</sup>)–N coupling and cyclization of 2-(2-bromoaryl)- and 2-(2-bromovinyl)imidazoles with 2-aminobenzimidazoles as building blocks under microwave irradiation.

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4

Gupta, Vijay, Satish K. Pandey, and Ravi P. Singh. "Facile synthesis of triphenylenes and triphenylene/phenanthrene fused heteroaromatics." Organic & Biomolecular Chemistry 16, no. 39 (2018): 7134–38. http://dx.doi.org/10.1039/c8ob01930d.

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5

Potikha, Lyudmyla, Volodymyr Kovtunenko, Arsen Turelyk, Aleksandr Turov, and Andrei Tolmachev. "Synthesis of Fused Pyrido[ a ]imidazoles." Synthetic Communications 38, no. 12 (2008): 2061–70. http://dx.doi.org/10.1080/00397910801997868.

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6

Patel, Alpa, Swee Y. Sharp, Katelan Hall, et al. "Fused imidazoles as potential chemical scaffolds for inhibition of heat shock protein 70 and induction of apoptosis. Synthesis and biological evaluation of phenanthro[9,10-d]imidazoles and imidazo[4,5-f][1,10]phenanthrolines." Organic & Biomolecular Chemistry 14, no. 16 (2016): 3889–905. http://dx.doi.org/10.1039/c6ob00471g.

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7

Abel, Steven-Alan G., Mathew O. Eglinton, James K. Howard, Dylan J. Hunt, Rolf H. Prager, and Jason A. Smith. "Synthesis of Heterocyclic-fused Imidazoles by Pyrolysis of N-Heterocyclic Isoxazol-5(2H)-ones." Australian Journal of Chemistry 67, no. 9 (2014): 1228. http://dx.doi.org/10.1071/ch14119.

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The synthesis of heterocyclic-fused imidazoles was achieved by flash vacuum pyrolysis (FVP) of N-heterocyclic isoxazol-5(2H)-ones via an iminocarbene intermediate. Unlike iminocarbenes generated from triazoles, no structural rearrangements were observed during the current synthesis method. We also demonstrated that less volatile isoxazol-5(2H)-one derivatives yield the corresponding imidazoles by condensed phase pyrolysis.

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8

Sharma, Pankaj, Chris LaRosa, Janet Antwi, Rajgopal Govindarajan, and Karl A. Werbovetz. "Imidazoles as Potential Anticancer Agents: An Update on Recent Studies." Molecules 26, no. 14 (2021): 4213. http://dx.doi.org/10.3390/molecules26144213.

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Nitrogen-containing heterocyclic rings are common structural components of marketed drugs. Among these heterocycles, imidazole/fused imidazole rings are present in a wide range of bioactive compounds. The unique properties of such structures, including high polarity and the ability to participate in hydrogen bonding and coordination chemistry, allow them to interact with a wide range of biomolecules, and imidazole-/fused imidazole-containing compounds are reported to have a broad spectrum of biological activities. This review summarizes recent reports of imidazole/fused imidazole derivatives a

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9

Kavina, M. A., V. V. Sizov, and I. P. Yakovlev. "Fused Imidazoles: I. Synthesis of 6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole Derivatives." Russian Journal of Organic Chemistry 54, no. 6 (2018): 901–11. http://dx.doi.org/10.1134/s107042801806012x.

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10

Singh, Davinder, Javeed Ahmad Tali, Gulshan Kumar, and Ravi Shankar. "Metal-free oxidative decarbonylative halogenation of fused imidazoles." New Journal of Chemistry 45, no. 44 (2021): 20551–55. http://dx.doi.org/10.1039/d1nj04440k.

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11

Kovtunenko, Volodimir, Lyudmila Potikha та Aleksandr Turov. "Synthesis of Fused Imidazoles Based on γ‐Bromodypnone". Synthetic Communications 34, № 19 (2004): 3609–13. http://dx.doi.org/10.1081/scc-200031044.

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12

Edmondson, Scott D., Anthony Mastracchio, Jason M. Cox, et al. "Aminopiperidine-fused imidazoles as dipeptidyl peptidase-IV inhibitors." Bioorganic & Medicinal Chemistry Letters 19, no. 15 (2009): 4097–101. http://dx.doi.org/10.1016/j.bmcl.2009.06.011.

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13

Saha, Argha, Asim Jana, and Lokman H. Choudhury. "Lemon juice mediated multicomponent reactions for the synthesis of fused imidazoles." New Journal of Chemistry 42, no. 22 (2018): 17909–22. http://dx.doi.org/10.1039/c8nj03480j.

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A green approach for the synthesis of diverse medicinally important tricyclic fused imidazoles has been described using one-pot multicomponent reactions in lemon juice as a biocatalyst as well as the reaction medium.

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14

Hu, Yong-Ji, Yu Zhou, Jing-Jing Gao, et al. "I₂-Mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides: selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles." Organic Chemistry Frontiers 9, no. 5 (2022): 1403–9. http://dx.doi.org/10.1039/d1qo01940f.

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An I2-mediated [3 + 2] annulation to access fused imidazoles from methyl-azaarenes and alkyl 2-isocyanoacetates was developed. This method can be used for the structural modification of natural products, gram scale reactions and further transformations.

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15

Wang, Huinan, Shengbao Lin, Hui Hong, et al. "Photo-induced decarboxylative radical cascade cyclization of unactivated alkenes: access to CF- and CF₂-substituted ring-fused imidazoles." RSC Advances 15, no. 16 (2025): 12739–45. https://doi.org/10.1039/d5ra02023a.

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A mild and effective visible-light-induced decarboxylative radical cascade reaction of olefin-containing imidazoles and α-fluorinated carboxylic acids, has been developed to afford monofluoromethylated or aryldifluoromethylated polycyclic imidazoles.

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16

Chen, Yingzhong, H. V. Rasika Dias, and Carl J. Lovely. "Synthesis of fused bicyclic imidazoles by ring-closing metathesis." Tetrahedron Letters 44, no. 7 (2003): 1379–82. http://dx.doi.org/10.1016/s0040-4039(02)02864-2.

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17

Kavina, M. A., V. V. Sizov, and I. P. Yakovlev. "Fused Imidazoles: II. Synthesis of Nitro Derivatives of 6,7-Dihydro-5H-pyrrolo[1,2-a]imidazoles." Russian Journal of Organic Chemistry 54, no. 11 (2018): 1689–96. http://dx.doi.org/10.1134/s1070428018110118.

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18

Hu, Qiong, Lidong Li, Fei Yin, et al. "Fused multifunctionalized isoindole-1,3-diones via the coupled oxidation of imidazoles and tetraynes." RSC Adv. 7, no. 78 (2017): 49810–16. http://dx.doi.org/10.1039/c7ra08817e.

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19

Barluenga, J., J. Garciá-Rodrígez, S. Martínez, A. Suárez-Sobrino, and M. Tomás. "Synthesis of Fused Imidazoles from Fischer Carbenes and 1,4-Diazafulvenes." Synfacts 2006, no. 8 (2006): 0764. http://dx.doi.org/10.1055/s-2006-941978.

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20

Atzrodt, Jens, Rainer Beckert, Wolfgang Günther, and Helmar Görls. "Nucleophilic Substitution of 4H-Imidazoles - A Key Step in the Synthesis of Fused Imidazoles and New Chromophores." European Journal of Organic Chemistry 2000, no. 8 (2000): 1661–68. http://dx.doi.org/10.1002/(sici)1099-0690(200004)2000:8<1661::aid-ejoc1661>3.0.co;2-1.

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21

Rahul, Singh, Pandrala Mallesh, V. Malhotra Sanjay, P. Pawar Ganesh, D. Chaudhari Vinod, and B. Salunke Deepak. "Design, synthesis, anti-cancer screening and structure activity relationship studies of biphenyl linked fused imidazoles." Journal of Indian Chemical Society Vol. 97, Aug 2020 (2020): 1237–44. https://doi.org/10.5281/zenodo.5656258.

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Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh-160 014, India Department of Cell, Development and Cancer Biology, Center for Experimental Therapeutics, Knight Cancer Institute, Oregon Health and Science University, Portland, OR 97201 Division of Medicinal Chemistry, CSIR-Institute of Microbiology Technology Chandigarh, Sector-39A, Chandigarh-160 036, India Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201 002, Uttar Pradesh, India National Interdisciplinary Centre of Vaccine, Immunotherapeutic and Antimicrobials, Panjab Uni

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22

Andreani, A., M. Rambaldi, A. Locatelli, R. Bossa, G. Salvatore, and I. Galatulas. "Synthesis and cardiotonic activity of aryl- or pyridyl-substituted fused imidazoles." European Journal of Medicinal Chemistry 29, no. 5 (1994): 339–42. http://dx.doi.org/10.1016/0223-5234(94)90057-4.

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23

Satyam, Killari, V. Murugesh та Surisetti Suresh. "The base-free van Leusen reaction of cyclic imines on water: synthesis of N-fused imidazo 6,11-dihydro β-carboline derivatives". Organic & Biomolecular Chemistry 17, № 21 (2019): 5234–38. http://dx.doi.org/10.1039/c9ob00660e.

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24

Lakshman, Shaik, N. Srinivasa Rao, Sridevi Kadgamala, B. V. Durgarao, N. Krishnarao, and Bhagavathula S. Diwakar. "TiO₂ nanoparticles as reusable catalysts for the efficient synthesis of 2, 4, 5-trisubstituted-1H-imidazoles." Journal of Physics: Conference Series 2765, no. 1 (2024): 012026. http://dx.doi.org/10.1088/1742-6596/2765/1/012026.

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Abstract A simple, highly efficient and eco-friendly protocol for the synthesis of 2,4,5-trisubstituted-1H-imidazoles via one-pot three component condensation of benzil, aldehydes and ammonium acetate under solvent-free conditions has been achieved utilizing TiO2. The applicability of this procedure was investigated further in relation to the synthesis of fused imidazoles that exhibit structural versatility. The remarkable features of this methodology are excellent yields in shorter reaction times, cleaner reaction profile, and environmentally benign nature, use of non-toxic, readily synthesiz

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25

Goel, Kapil Kumar, Rajeev Kharb, and Satyendra Kumar Rajput. "Design, Synthesis and Biological Evaluation of Imidazole-Substituted/Fused Aryl Derivatives Targeting Tubulin Polymerization as Anticancer Agents." SynOpen 07, no. 01 (2023): 17–28. http://dx.doi.org/10.1055/s-0042-1751835.

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AbstractThe development of new pharmacologically active molecules targeting tubulin polymerization has recently attracted great interest in research groups. In efforts to develop new potent anticancer compounds, imidazole-tethered/fused pharmacologically active aryl derivatives possessing different substitution patterns targeting tubulin polymerization have been rationally designed and synthesized. The target molecules (P1-5 and KG1-5) were synthesized by multistep syntheses involving the reaction of intermediate 2-aminophenyl-tethered imidazoles with appropriate reactants in the presence of p

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26

Atzrodt, Jens, Rainer Beckert, Wolfgang Guenther, and Helmar Goerls. "ChemInform Abstract: Nucleophilic Substitution of 4H-Imidazoles - A Key Step in the Synthesis of Fused Imidazoles and New Chromophores." ChemInform 32, no. 2 (2001): no. http://dx.doi.org/10.1002/chin.200102120.

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27

B., SURENDER REDDY, BUCHI REDDY R., V. P. CHANDRA MOULI G., and D. REDDY Y. "Synthesis of New 1-Aryl-2H-benzimidazolo[2, 1-e] imidazoles." Journal of Indian Chemical Society Vol. 65, Dec 1988 (1988): 853–54. https://doi.org/10.5281/zenodo.6090216.

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Department of Chemistry, Regional Engineering College, Warangal-506 004. <em>Manuscript received 19 February 1988, accepted 1 September 1988</em> The condensation of <em>o</em>-phenylenediamine with glycine in acid medium gave 2-aminomethylbenzimidazole dihydrochloride. The reaction or 2-aminomethylbenzimidazole dihydrochloride with the aromatic aldehydes Ia alkaline medium afforded fused benzimidazolo[2,1- <em>e</em>] imidazole derivatives. They were screened for antimicrobial activity.  

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28

Vessally, Esmail, Somayeh Soleimani-Amiri, Akram Hosseinian, Ladan Edjlali, and Ahmadreza Bekhradnia. "New protocols to access imidazoles and their ring fused analogues: synthesis from N-propargylamines." RSC Advances 7, no. 12 (2017): 7079–91. http://dx.doi.org/10.1039/c6ra25816f.

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29

Kumar, Sonu, Manash P. Sarmah, Yella Reddy, Ashish Bhatt, and Ravi Kant. "A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles." Synthetic Communications 52, no. 1 (2021): 96–105. http://dx.doi.org/10.1080/00397911.2021.2001658.

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30

Szczepankiewicz, Bruce G., Jeffrey J. Rohde, and Ravi Kurukulasuriya. "Synthesis of Purines and Other Fused Imidazoles from Acyclic Amidines and Guanidines." Organic Letters 7, no. 9 (2005): 1833–35. http://dx.doi.org/10.1021/ol0504751.

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31

Aly, Sara, Mikhail Romashko, and Bruce A. Arndtsen. "Multicomponent Synthesis of Substituted and Fused-Ring Imidazoles via Phospha-münchnone Cycloaddition." Journal of Organic Chemistry 80, no. 5 (2015): 2709–14. http://dx.doi.org/10.1021/jo5028936.

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32

Guchhait, Sankar K., and Vikas Chaudhary. "Desilylative activation of TMSCN in chemoselective Strecker–Ugi type reaction: functional fused imidazoles as building blocks as an entry route to annulated purines." Org. Biomol. Chem. 12, no. 34 (2014): 6694–705. http://dx.doi.org/10.1039/c4ob00882k.

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Nucleophilic activation of TMSCN as an isocyanide equivalent by DABCO–THF in the Strecker–Ugi reaction facilitates the synthesis of functional imidazoles which, as building blocks, afford access to C8–N9 annulated purines.

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33

U., C. Mashelkar, and A. Audi A. "Synthesis of some novel 4-substituted coumarins having antibacterial activity (Part-I)." Journal of Indian Chemical Society Vol. 82, Mar 2005 (2005): 254–57. https://doi.org/10.5281/zenodo.5827011.

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Organic Research Laboratory. SS & LS Patkar College, Goregaon (W). Mumbai-400 062, India E-mail: ajayaaudi@rediffmail.com                                                        Fax : 91-22-28744755 <em>Manuscript received 13 February 2004, revised 1 September 2004, accepted 24 November 2004</em> Methyl coumarin-4-methyl acetate on bromination in dioxane or dichloroethane as solvent resulted in sidechain bromination giving a-bromo derivative. The same r

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34

Gracias, Vijaya, Alan F. Gasiecki, and Stevan W. Djuric. "Synthesis of Fused Bicyclic Imidazoles by Sequential Van Leusen/Ring-Closing Metathesis Reactions." Organic Letters 7, no. 15 (2005): 3183–86. http://dx.doi.org/10.1021/ol050852+.

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35

Zhao, Dongbing, Junyi Hu, Ningjie Wu, et al. "Regiospecific Synthesis of 1,2-Disubstituted (Hetero)aryl Fused Imidazoles with Tunable Fluorescent Emission." Organic Letters 13, no. 24 (2011): 6516–19. http://dx.doi.org/10.1021/ol202807d.

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36

ANDREANI, A., A. LEONI, R. MORIGI, R. BOSSA, M. CHIERICOZZI, and I. GALATULAS. "ChemInform Abstract: In vivo Cardiotonic Activity of Aryl- and Pyridyl-substituted Fused Imidazoles." ChemInform 29, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199828159.

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37

ANDREANI, A., M. RAMBALDI, A. LOCATELLI, R. BOSSA, G. SALVATORE, and I. GALATULAS. "ChemInform Abstract: Synthesis and Cardiotonic Activity of Aryl- or Pyridyl-Substituted Fused Imidazoles." ChemInform 25, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.199443143.

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38

Chen, Zhong-Zhu, Shi-Qiang Li, Wen-Li Liao, et al. "Efficient method for the synthesis of fused benzimidazole–imidazoles via deprotection and cyclization reactions." Tetrahedron 71, no. 44 (2015): 8424–27. http://dx.doi.org/10.1016/j.tet.2015.09.008.

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39

Pastor, J., S. Martínez, R. M. Álvarez, et al. "177 Amino-carbonyl substituted fused imidazoles: potent, selective and orally bioavailable inhibitors of PI3K." European Journal of Cancer Supplements 8, no. 7 (2010): 61. http://dx.doi.org/10.1016/s1359-6349(10)71882-6.

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40

Pastor, J., S. Martínez, R. M. Álvarez, et al. "183 Amino-alkyl substituted fused imidazoles: potent, selective and orally bioavailable inhibitors of PI3K." European Journal of Cancer Supplements 8, no. 7 (2010): 62. http://dx.doi.org/10.1016/s1359-6349(10)71888-7.

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41

Aly, Sara, Mikhail Romashko, and Bruce A. Arndtsen. "ChemInform Abstract: Multicomponent Synthesis of Substituted and Fused-Ring Imidazoles via Phospha-Muenchnone Cycloaddition." ChemInform 46, no. 29 (2015): no. http://dx.doi.org/10.1002/chin.201529171.

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42

Gambouz, Khadija, Mohsine Driowya, Mohammed Loubidi, et al. "Unusual rearrangement of imidazo[1,5-a]imidazoles and imidazo[1,2-b]pyrazoles into imidazo[1,5-a]pyrimidines and pyrazolo[1,5-a]pyrimidines." RSC Advances 9, no. 50 (2019): 29051–55. http://dx.doi.org/10.1039/c9ra04609g.

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43

Cho, Analia Young Hwa, Hery Chung, Javier Romero-Parra, et al. "Motifs in Natural Products as Useful Scaffolds to Obtain Novel Benzo[d]imidazole-Based Cannabinoid Type 2 (CB2) Receptor Agonists." International Journal of Molecular Sciences 24, no. 13 (2023): 10918. http://dx.doi.org/10.3390/ijms241310918.

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The endocannabinoid system (ECS) constitutes a broad-spectrum modulator of homeostasis in mammals, providing therapeutic opportunities for several pathologies. Its two main receptors, cannabinoid type 1 (CB1) and type 2 (CB2) receptors, mediate anti-inflammatory responses; however, their differing patterns of expression make the development of CB2-selective ligands therapeutically more attractive. The benzo[d]imidazole ring is considered to be a privileged scaffold in drug discovery and has demonstrated its versatility in the development of molecules with varied pharmacologic properties. On th

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44

Lantos, Ivan, and Michael McGuire. "Novel Syntheses of Fused-imidazoles III. Simplified Construction of the Imidazo[2,1-b]thiazoline System." HETEROCYCLES 24, no. 4 (1986): 991. http://dx.doi.org/10.3987/r-1986-04-0991.

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45

Zhao, Dongbing, Junyi Hu, Ningjie Wu, et al. "ChemInform Abstract: Regiospecific Synthesis of 1,2-Disubstituted (Hetero)aryl Fused Imidazoles with Tunable Fluorescent Emission." ChemInform 43, no. 15 (2012): no. http://dx.doi.org/10.1002/chin.201215119.

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46

Singh, Dharmender, Vipin Kumar, Nisha Devi, Chandi C. Malakar, Ravi Shankar та Virender Singh. "Metal-free Decarboxylative Amination: An Alternative Approach Towards Regioselective Synthesis of β-CarbolineN-fused Imidazoles". Advanced Synthesis & Catalysis 359, № 7 (2017): 1213–26. http://dx.doi.org/10.1002/adsc.201600970.

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47

Frank, Birgit, Rainer Beckert, Sven Rau, and Helmar Görls. "2-Azaanthraquinones: Building Blocks for New Ring-Fused Imidazoles and their Transformation into Benzo[f]isoindole-4,9-diones." Zeitschrift für Naturforschung B 60, no. 7 (2005): 771–79. http://dx.doi.org/10.1515/znb-2005-0713.

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The modification of 2-azaanthraquinones with selected C1 building blocks gives a series of new imidazo-fused derivatives. Employing 2,3-dichloro-5,6-dicyanopyrazine as cyclization partner a rearrangement to yield derivatives of benzo[f ]isoindole-4,9-dione takes place. The Sonogashira crosscoupling reaction of the aminalester derivative of the azaanthraquinone resulted in well soluble silyl substituted acetylenes as well as ethinyl aniline which allows further derivatization reactions.

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48

Soares, Maria I. L., Ana C. F. de Lyra, Marta S. C. Henriques, José A. Paixão, and Teresa M. V. D. Pinho e Melo. "Thermolysis of 1-(thiophen-2-yl)-1H-tetrazoles: a route to thiophene-fused imidazoles and pyrimidines." Tetrahedron 71, no. 21 (2015): 3343–50. http://dx.doi.org/10.1016/j.tet.2015.03.102.

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49

Frutos, Rogelio P., and Michael Johnson. "Regiocontrolled synthesis of highly-functionalized fused imidazoles: a novel synthesis of second generation LFA-1 inhibitors." Tetrahedron Letters 44, no. 34 (2003): 6509–11. http://dx.doi.org/10.1016/s0040-4039(03)01535-1.

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50

Chen, Zhong-Zhu, Shi-Qiang Li, Wen-Li Liao, et al. "ChemInform Abstract: Efficient Method for the Synthesis of Fused Benzimidazole-Imidazoles via Deprotection and Cyclization Reactions." ChemInform 47, no. 5 (2016): no. http://dx.doi.org/10.1002/chin.201605148.

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