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Journal articles on the topic 'Imidazo[1,5-a]azines'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

Pelletier, Guillaume, and André B. Charette. "Triflic Anhydride Mediated Synthesis of Imidazo[1,5-a]azines." Organic Letters 15, no. 9 (2013): 2290–93. http://dx.doi.org/10.1021/ol400870b.

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2

Pelletier, Guillaume, and Andre B. Charette. "ChemInform Abstract: Triflic Anhydride Mediated Synthesis of Imidazo[1,5-a]azines." ChemInform 44, no. 36 (2013): no. http://dx.doi.org/10.1002/chin.201336149.

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3

Sustac Roman, Daniela, Valentin Poiret, Guillaume Pelletier, and André B. Charette. "Direct Arylation of Imidazo[1,5-a]azines Through Ruthenium and Palladium Catalysis." European Journal of Organic Chemistry 2015, no. 1 (2014): 67–71. http://dx.doi.org/10.1002/ejoc.201403268.

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4

Sustac Roman, Daniela, Valentin Poiret, Guillaume Pelletier, and Andre B. Charette. "ChemInform Abstract: Direct Arylation of Imidazo[1,5-a]azines Through Ruthenium and Palladium Catalysis." ChemInform 46, no. 20 (2015): no. http://dx.doi.org/10.1002/chin.201520192.

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5

Sharma, Shubham, Avijit Kumar Paul, and Virender Singh. "La(OTf)3-catalysed one-pot synthesis of pyrazole tethered imidazo[1,2-a]azine derivatives and evaluation of their light emitting properties." New Journal of Chemistry 44, no. 3 (2020): 684–94. http://dx.doi.org/10.1039/c9nj05426j.

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6

Kolar, Patrik, and Miha Tišler. "A New Route to Imidazo(1,5-a)pyridines and -quinolines." Zeitschrift für Naturforschung B 46, no. 8 (1991): 1110–12. http://dx.doi.org/10.1515/znb-1991-0822.

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7

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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8

Chen, Li-Hsun, Chih-Hsien Kao, Sandip Dhole, et al. "Regioselective synthesis of imidazo[1,5-a]quinoxalines and methyl N-phenylbenzimidats on an ionic liquid support." RSC Advances 6, no. 80 (2016): 76123–27. http://dx.doi.org/10.1039/c6ra11861e.

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An ionic liquid supported synthesis of imidazo[1,5-a]quinoxalines and methyl N-phenylbenzimidats was explored to generate polycyclic imidazo[1,5-a]quinoxalines and methyl N-phenylbenzimidats during the cleavage of the support.

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9

Hannah, Duncan R., and Malcolm F. G. Stevens. "Structural Studies on Bioactive Compounds. Part 38.1 Reactions of 5-Aminoimidazole-4-Carboxamide: Synthesis of Imidazo[1,5-a]Quinazoline-3-Carboxamides." Journal of Chemical Research 2003, no. 7 (2003): 398–401. http://dx.doi.org/10.3184/030823403103174533.

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5-Aminoimidazole-4-carboxamide reacts with aromatic aldehydes to afford Schiff bases which can be cyclised to imidazo[1,5- a]quinazoline-3-carboxamides in DMF/sodium hydride. The potassium salt of imidazo[1,5- a]quinazoline-3-carboxylic acid undergoes deuterium exchange in D2O at the 1-position.

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10

Gad-Elkareem, Mohamed A. M., Azza M. Abdel-Fattah, and Mohamed A. A. Elneairy. "Pyrazolo[3,4-b]pyridine in heterocyclic synthesis: synthesis of new pyrazolo[3,4-b]pyridines, imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines, and pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines." Canadian Journal of Chemistry 85, no. 9 (2007): 592–99. http://dx.doi.org/10.1139/v07-089.

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Pyrazolo[3,4-b]pyridine derivatives 7 and 9 were synthesized via the reaction of 3-amino-1H-pyrazolo-[3,4-b]pyridine derivative 2 with ω-bromoacetophenones. Reaction of 7 and 9 with Ac2O afforded the imidazo[1',2':1,5]py razolo[3,4-b]pyridine derivative 8 and pyrazolo[3,4-b]pyridine derivative 10, respectively. Reaction of 2 with chloroacetonitrile followed by DMF-DMA gave imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines 4 and 5, respectively. Acetyl acetone and 1,1-dicyano-2,2-dimethylthioethene were reacted with 2 to afford the pyrido[2',3':3,4]pyrazolo-[1,5-a]-pyrimidines 11 and 14, respectively.

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11

Aziz, Jessy, and Sandrine Piguel. "An Update on Direct C–H Bond Functionalization of Nitrogen-Containing Fused Heterocycles." Synthesis 49, no. 20 (2017): 4562–85. http://dx.doi.org/10.1055/s-0036-1590859.

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This report highlights the recent advances in direct C–H bond functionalization of 5,5- and 6,5-fused heterocycles containing at least two nitrogen atoms. Besides C–C bond formation, C–N, C–S, C–P, and C–Si bonds can also be created via a metal-catalyzed process. Some examples, where a C–H functionalization approach was applied for the synthesis of drug candidates, will be presented as well.1 Introduction2 C–H Functionalization Reactions of N-Containing Heterocycles2.1 Imidazo[1,2-a]pyridines2.2 Pyrrolo[1,2-a]pyrazines2.3 Imidazo[1,2-b]pyrazoles2.4 Imidazo[1,2-a]pyrimidines2.5 Imidazo[1,2-a]py

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12

Joshi, Gaurav, Monika Chauhan, Rakesh Kumar, et al. "Cyclocondensation reactions of an electron deactivated 2-aminophenyl tethered imidazole with mono/1,2-biselectrophiles: synthesis and DFT studies on the rationalisation of imidazo[1,2-a]quinoxaline versus benzo[f]imidazo[1,5-a][1,3,5]triazepine selectivity switches." Organic Chemistry Frontiers 5, no. 24 (2018): 3526–33. http://dx.doi.org/10.1039/c8qo00706c.

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13

Kolar, Patrik, Andrej Petrič, Miha Tišler, and Fulvia Felluga. "Heterocycles from amino acids. A novel synthetic approach for imidazo[1,5-a]pyridines and imidazo[1,5-a]quinolines." Journal of Heterocyclic Chemistry 28, no. 7 (1991): 1715–20. http://dx.doi.org/10.1002/jhet.5570280712.

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14

Kutschy, Peter, Mojmír Suchý, Milan Dzurilla, Mitsuo Takasugi, and Vladimír Kováčik. "A New Approach to Imidazo[1,5-a]indole Derivatives." Collection of Czechoslovak Chemical Communications 65, no. 7 (2000): 1163–72. http://dx.doi.org/10.1135/cccc20001163.

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Reaction of indole-2-carbonyl isothiocyanate (1) with sodium methanethiolate afforded 1-thioxo-1H-imidazo[1,5-a]indol-3(2H)-one (3). Its methylation with methyl iodide in the presence of lithium hydride in dimethylformamide, or potassium carbonate in acetone resulted in the formation of corresponding S- and N-methyl derivatives 4 and 5. N-(Indole-2-carbonyl)thiocarbamates and N-(indole-2-carbonyl)thioureas prepared by treatment of isothiocyanate 1 with corresponding nucleophilic reagents were S-methylated with methyl iodide in acetone in the presence of potassium carbonate. The obtained N-(ind

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15

Ramírez-López, Sandra C., M. V. Basavanag Unnamatla, and Rocío Gámez-Montaño. "Solvent-Free Synthesis of Imidazo [1,2-a] pyridin-tetrazolo [1,5-a] Quinolines via an IMCR One-Pot Process." Proceedings 9, no. 1 (2018): 41. http://dx.doi.org/10.3390/ecsoc-22-05796.

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A solvent-free and catalyst-free synthesis of fused bis-heterocycles containing imidazo[1,2-a]pyridine and tetrazolo[1,5-a]quinoline frameworks is reported via a one-pot process. This Groebke–Blackburn–Bienaymé reaction (GBBR)/SNAr/ring-chain azido tautomerization cascade proceeds under eco-friendly conditions. The tetrazolo[1,5-a]quinoline and imidazo[1,2-a]pyridine scaffolds are present in various compounds with interesting pharmacological properties and could lead to the discovery of novel bioactive molecules.

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16

Schubert, Hermann, and Jens Fischer. "1,2-Dihydro-3H-imidazo[1,5-a]benzimidazole." Zeitschrift für Chemie 11, no. 1 (2010): 9–10. http://dx.doi.org/10.1002/zfch.19710110103.

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17

Patinote, Cindy, Nour Bou Karroum, Georges Moarbess, et al. "Imidazo[1,2- a ]pyrazine, Imidazo[1,5- a ]quinoxaline and Pyrazolo[1,5- a ]quinoxaline derivatives as IKK1 and IKK2 inhibitors." European Journal of Medicinal Chemistry 138 (September 2017): 909–19. http://dx.doi.org/10.1016/j.ejmech.2017.07.021.

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18

Loubidi, M., M. Lorion, A. El Hakmaoui, P. Bernard, M. Akssira, and G. Guillaumet. "One-Step Synthesis of 1H-Imidazo[1,5-a]imidazole Scaffolds and Access to their Polyheterocycles." Synthesis 51, no. 21 (2019): 3973–80. http://dx.doi.org/10.1055/s-0039-1690182.

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In this work, we continue our adventure in the chemistry of 5-5 tri-nitrogen bicycles. We disclose herein a one-step reaction to synthesize 1H-imidazo[1,5-a]imidazoles with different substituents introduced through the use of a wide range of aldehydes and isocyanides by using a Groebke–Blackburn–Bienaymé multicomponent reaction. The aim is to build a new library of 1H-imidazo[1,5-a]imidazole scaffolds. This bicycle was then modified to access new nitrogen-containing polycyclic compounds.

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19

El-Abadelah, Mustafa M., Firas F. Awwadi, Ahmad H. Abdullah, and Wolfgang Voelter. "The reaction of imidazo[1,5-a]pyridines with ninhydrin revisited." Zeitschrift für Naturforschung B 75, no. 6-7 (2020): 559–65. http://dx.doi.org/10.1515/znb-2020-0027.

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AbstractThe synthesis of 2,2′-(Imidazo[1,5-a]pyridine-1,3-diyl)bis(2-hydroxy-1H-indene-1,3(2H)-dione) (11) is achieved by reaction of imidazo[1,5-a]pyridine (7) with two equivalents of ninhydrin (1) at room temperature. The structure of this new 1,3-bis-adduct 11 is evidenced from HRMS and NMR spectral data and confirmed by single-crystal X-ray crystallography. Employment of equimolar amounts of 1 and 7 gave a separable mixture of the respective 1- and 3-monomeric adducts (9, 10).

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20

Mamedov, V. A., and A. A. Kalinin. "Advances in the synthesis of imidazo[1,5-a]- and imidazo[1,2-a]quinoxalines." Russian Chemical Reviews 83, no. 9 (2014): 820–47. http://dx.doi.org/10.1070/rc2014v083n09abeh004424.

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21

Wu, Song-Song, Cheng-Tao Feng, Di Hu, et al. "Iodine-catalyzed direct C–H thiolation of imidazo[1,5-a]quinolines for the synthesis of 3-sulfenylimidazo[1,5-a]quinolines." Organic & Biomolecular Chemistry 15, no. 7 (2017): 1680–85. http://dx.doi.org/10.1039/c6ob02736a.

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22

Gerecke, Max, Emilio Kyburz, René Boner, and Walter Gassner. "New Tetracyclic Derivatives of Imidazo[1,5-a][1,4]benzodiazepines and of Imidazo[1,5-a]-thieno[3,2-f][1,4]-diazepines." HETEROCYCLES 39, no. 2 (1994): 693. http://dx.doi.org/10.3987/com-94-s(b)61.

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23

KOLAR, P., A. PETRIC, M. TISLER, and F. FELLUGA. "ChemInform Abstract: Heterocycles from Amino Acids. A Novel Synthetic Approach for Imidazo( 1,5-a)pyridines and Imidazo(1,5-a)quinolines." ChemInform 23, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199211183.

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24

Zhang, Xuan, Guang-Jie Song, Xiang-Jian Cao, et al. "A new fluorescent pH probe for acidic conditions." RSC Advances 5, no. 109 (2015): 89827–32. http://dx.doi.org/10.1039/c5ra14174e.

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25

Buvaylo, Elena A., Vladimir N. Kokozay, Rostyslav P. Linnik, Olga Yu Vassilyeva, and Brian W. Skelton. "Hybrid organic–inorganic chlorozincate and a molecular zinc complex involving the in situ formed imidazo[1,5-a]pyridinium cation: serendipitous oxidative cyclization, structures and photophysical properties." Dalton Transactions 44, no. 30 (2015): 13735–44. http://dx.doi.org/10.1039/c5dt01491c.

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26

Hlasta, Dennis J. "Regiospecific acylation reactions of imidazo[1,5-a]pyridine." Tetrahedron Letters 31, no. 41 (1990): 5833–34. http://dx.doi.org/10.1016/s0040-4039(00)97970-x.

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27

Verček, Bojan, and Tomaž Trček. "Synthesis of Highly Functionalized Imidazo[1,5-a]pyrazines." Synthesis 2006, no. 20 (2006): 3437–42. http://dx.doi.org/10.1055/s-2006-950211.

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28

Koto, Yuma, Fumitoshi Shibahara та Toshiaki Murai. "Imidazo[1,5-a]pyridin-3-ylidenes as π-accepting carbene ligands: substituent effects on properties of N-heterocyclic carbenes". Organic & Biomolecular Chemistry 15, № 8 (2017): 1810–20. http://dx.doi.org/10.1039/c6ob02827f.

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29

Sammor, Mervat S., Mustafa M. El-Abadelah, Ahmad Q. Hussein, Firas F. Awwadi, Salim S. Sabri, and Wolfgang Voelter. "A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin." Zeitschrift für Naturforschung B 73, no. 6 (2018): 413–21. http://dx.doi.org/10.1515/znb-2018-0039.

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AbstractThe reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines (1) with ninhydrin in dichloromethane at room temperature delivered good yields of the respective 2-hydroxy-2-(imidazo[1,5-a]pyridine-1-yl)indene-1,3-diones. In the presence of dimethyl acetylenedicarboxylate (DMAD), this uncatalyzed electrophilic substitution reaction, involving C-1 (in 1) and the central C=O (in ninhydrin), takes precedence over the three-component 1,4-dipolar cycloaddition reaction. This selectivity is probably due to the higher electrophilicity of the carbonyl carbon-2 in ninhydrin as compared to that of the sp-c

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30

Kamal, Ahmed, A. V. Subba Rao, V. Lakshma Nayak, et al. "Synthesis and biological evaluation of imidazo[1,5-a]pyridine-benzimidazole hybrids as inhibitors of both tubulin polymerization and PI3K/Akt pathway." Org. Biomol. Chem. 12, no. 48 (2014): 9864–80. http://dx.doi.org/10.1039/c4ob01930j.

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31

Hoshi, Keita, Masami Itaya, Koki Tahara, et al. "Two-photon excitable boron complex based on tridentate imidazo[1,5-a]pyridine ligand for heavy-atom-free mitochondria-targeted photodynamic therapy." RSC Advances 11, no. 42 (2021): 26403–7. http://dx.doi.org/10.1039/d1ra05059a.

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32

Xu, Zhiyang, Zhen Chen, Aikun Liu, Ruixue Ji, Xiaoqun Cao, and Yanqing Ge. "A ratiometric fluorescent probe for detection of exogenous mitochondrial SO2 based on a FRET mechanism." RSC Advances 9, no. 16 (2019): 8943–48. http://dx.doi.org/10.1039/c8ra10328c.

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33

Bou Karroum, Nour, Georges Moarbess, Jean-François Guichou, et al. "Novel and Selective TLR7 Antagonists among the Imidazo[1,2-a]pyrazines, Imidazo[1,5-a]quinoxalines, and Pyrazolo[1,5-a]quinoxalines Series." Journal of Medicinal Chemistry 62, no. 15 (2019): 7015–31. http://dx.doi.org/10.1021/acs.jmedchem.9b00411.

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34

Firmansyah, Dikhi, Marzena Banasiewicz, and Daniel T. Gryko. "Vertically-expanded imidazo[1,2-a]pyridines and imidazo[1,5-a]pyridine via dehydrogenative coupling." Organic & Biomolecular Chemistry 13, no. 5 (2015): 1367–74. http://dx.doi.org/10.1039/c4ob02383h.

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35

Crawforth, James M., and Melissa Paoletti. "A one-pot synthesis of imidazo[1,5-a]pyridines." Tetrahedron Letters 50, no. 34 (2009): 4916–18. http://dx.doi.org/10.1016/j.tetlet.2009.06.061.

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36

Hu, Zhiyuan, Jiao Hou, Jie Liu, Wenquan Yu, and Junbiao Chang. "Synthesis of imidazo[1,5-a]pyridines via I2-mediated sp3 C–H amination." Organic & Biomolecular Chemistry 16, no. 31 (2018): 5653–60. http://dx.doi.org/10.1039/c8ob01501e.

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37

Shen, Shi-Li, Xiao-Fan Zhang, Yan-Qing Ge, Yan Zhu, and Xiao-Qun Cao. "A mitochondria-targeting ratiometric fluorescent probe for the detection of hypochlorite based on the FRET strategy." RSC Advances 7, no. 87 (2017): 55296–300. http://dx.doi.org/10.1039/c7ra11086c.

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38

Schweizer, Edward E., John E. Hayes, S. N. Hirwe, and Arnold L. Rheingold. "Reactions of azines. 9. Preparation of 4,5-dihydropyrazolo[1,5-a]pyridines, 6,7-dihydropyrazolo[1,5-a]pyridines, and pyrazolo[1,5-a]pyridines." Journal of Organic Chemistry 52, no. 7 (1987): 1319–24. http://dx.doi.org/10.1021/jo00383a028.

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39

Attanasi, Orazio A., Gianfranco Favi, Gianluca Giorgi, Roberta Majer, Francesca Romana Perrulli, and Stefania Santeusanio. "Access to novel imidazo[1,5-a]pyrazine scaffolds by the combined use of a three-component reaction and a base-assisted intramolecular cyclization." Org. Biomol. Chem. 12, no. 26 (2014): 4610–19. http://dx.doi.org/10.1039/c4ob00676c.

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40

Sheng, Jie, Jidan Liu, He Zhao, Liyao Zheng, and Xingchuan Wei. "Metal-free synthesis of imidazo[1,5-a]pyridines via elemental sulfur mediated sequential dual oxidative Csp3–H amination." Organic & Biomolecular Chemistry 16, no. 31 (2018): 5570–74. http://dx.doi.org/10.1039/c8ob01391h.

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41

Donthiboina, Kavitha, Hari Krishna Namballa, Siddiq Pasha Shaik, Jagadeesh Babu Nanubolu, Nagula Shankaraiah, and Ahmed Kamal. "Iodine promoted dual oxidative C(sp3)–H amination of 2-methyl-3-arylquinazolin-4(3H)-ones: a facile route to 1,4-diarylimidazo[1,5-a]quinazolin-5(4H)-ones." Organic & Biomolecular Chemistry 16, no. 10 (2018): 1720–27. http://dx.doi.org/10.1039/c7ob02677c.

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42

Mennie, Katrina M., Michael H. Reutershan, Catherine White, et al. "Divergent and Regioselective Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines." Organic Letters 23, no. 12 (2021): 4694–98. http://dx.doi.org/10.1021/acs.orglett.1c01431.

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43

Xie, Zeqiang, Jiangling Peng, and Qiang Zhu. "Copper-mediated C(sp3)–H amination in a multiple C–N bond-forming strategy for the synthesis of N-heterocycles." Organic Chemistry Frontiers 3, no. 1 (2016): 82–86. http://dx.doi.org/10.1039/c5qo00313j.

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44

Liu, Jinna, Yuhua Cao, Lei Li, et al. "Titanium complexes supported by imidazo[1,5-a]pyridine-containing pyrrolyl ligand as catalysts for hydroamination and polymerization reactions, and as an antitumor reagent." RSC Advances 5, no. 14 (2015): 10318–25. http://dx.doi.org/10.1039/c4ra14692a.

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45

Vassilyeva, Olga Yu, Elena A. Buvaylo, Vladimir N. Kokozay, Brian W. Skelton, and Alexandre N. Sobolev. "Crystal structures of an imidazo[1,5-a]pyridinium-based ligand and its (C13H12N3)2[CdI4] hybrid salt." Acta Crystallographica Section E Crystallographic Communications 75, no. 8 (2019): 1209–14. http://dx.doi.org/10.1107/s2056989019009964.

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The monocation product of the oxidative condensation–cyclization between two molecules of pyridine-2-carbaldehyde and one molecule of CH3NH2·HCl in methanol, 2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridinium, was isolated in the presence of metal ions as bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] tetraiodocadmate, (C13H12N3)2[CdI4], (I), and the mixed chloride/nitrate salt, bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] 1.5-chloride 0.5-nitrate trihydrate, 2C13H12N3 +·1.5Cl−·0.5NO3 −·3H2O, (II). Hybrid salt (I) crystallizes in the space group P21/n with two [L]2[CdI4]

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46

Alajarin, Ramón, Juan J. Vaquero, Julio Alvarez-Builla, et al. "Imidazo[1,5-a]pyrimidine and benzo[4,5]imidazo[1,2-a]pyrimidine derivatives as calcium antagonists." Bioorganic & Medicinal Chemistry 2, no. 5 (1994): 323–29. http://dx.doi.org/10.1016/s0968-0896(00)82188-4.

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47

Kalinin, V. A., and A. A. Mamedov. "ChemInform Abstract: Advances in the Synthesis of Imidazo[1,5-a]- and Imidazo[1,2-a]-quinoxalines." ChemInform 46, no. 14 (2015): no. http://dx.doi.org/10.1002/chin.201514308.

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48

Volpi, Giorgio, and Roberto Rabezzana. "Imidazo[1,5-a]pyridine derivatives: useful, luminescent and versatile scaffolds for different applications." New Journal of Chemistry 45, no. 13 (2021): 5737–43. http://dx.doi.org/10.1039/d1nj00322d.

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In the last few years, imidazo[1,5-a]pyridine nuclei and derivatives have attracted growing attention due to their unique chemical structure and versatility, optical behaviours, and biological properties.

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49

Aksenov, Dmitrii A., Nikolai A. Arutiunov, Vladimir V. Maliuga, Alexander V. Aksenov, and Michael Rubin. "Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes." Beilstein Journal of Organic Chemistry 16 (November 26, 2020): 2903–10. http://dx.doi.org/10.3762/bjoc.16.239.

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Imidazo[1,5-a]pyridines were efficiently prepared via the cyclization of 2-picolylamines with nitroalkanes electrophilically activated in the presence of phosphorous acid in polyphosphoric acid (PPA) medium.

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Moarbess, Georges, Carine Deleuze-Masquefa, Vanessa Bonnard, et al. "In vitro and in vivo anti-tumoral activities of imidazo[1,2-a]quinoxaline, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline derivatives." Bioorganic & Medicinal Chemistry 16, no. 13 (2008): 6601–10. http://dx.doi.org/10.1016/j.bmc.2008.05.022.

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