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Journal articles on the topic 'Indolizine – Derivatives'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Sekgota, Khethobole C., Michelle Isaacs, Heinrich C. Hoppe, et al. "Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids." Journal of Chemical Research 45, no. 7-8 (2021): 674–78. http://dx.doi.org/10.1177/1747519820987156.

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Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by saponification of the corresponding methyl esters produced, in turn, selectively and efficiently, by time-controlled cyclisation of a single Morita–Baylis–Hillman adduct. Various amino and hydrazino compounds with medicinal potential have been used to prepare indolizine-2-carboxamido and hydrazido derivatives.

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2

Zhang, Yi-Zhu, Feng-Tao Sheng, Zuoquan Zhu, et al. "Organocatalytic C3-functionalization of indolizines: synthesis of biologically important indolizine derivatives." Organic & Biomolecular Chemistry 18, no. 29 (2020): 5688–96. http://dx.doi.org/10.1039/d0ob01230k.

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A Brønsted acid-catalyzed C3-alkylation of indolizines has been established with different electrophiles (E), which synthesized a series of C3-functionalized indolizines in overall good yields (up to 89%).

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3

Cai, Qun, Yan-Ping Zhu, Yang Gao, Jing-Jing Sun, and An-Xin Wu. "A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives." Canadian Journal of Chemistry 91, no. 6 (2013): 414–19. http://dx.doi.org/10.1139/cjc-2012-0534.

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A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylide synthesis, and 1,3-dipolar cycloaddition. The protocols were found to be highly efficient in terms of high yields, operational simplicity, mild reaction conditions, and easy workup. This method has provided an important supplement for the synthesis of indolizine derivatives via a novel tandem synthesis.

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4

Au-Alvarez, O., V. A. Tafeenko, and L. A. Aslanov. "Structural study of indolizine derivatives." Acta Crystallographica Section A Foundations of Crystallography 52, a1 (1996): C274. http://dx.doi.org/10.1107/s010876739608854x.

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5

Bonnaud, Bernard, Dennis Bigg, and Jean-François Patoiseau. "Synthesis of novel indolizine derivatives." Journal of Heterocyclic Chemistry 28, no. 8 (1991): 1927–32. http://dx.doi.org/10.1002/jhet.5570280820.

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6

López, Luis A., and Javier González. "Copper(i)-carbenes as key intermediates in the [3 + 2]-cyclization of pyridine derivatives with alkenyldiazoacetates: a computational study." Organic & Biomolecular Chemistry 17, no. 3 (2019): 646–54. http://dx.doi.org/10.1039/c8ob02676a.

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This work reports a computational study of the copper(i)-catalyzed regioselective synthesis of indolizine derivatives through the [3 + 2]-cyclization reaction of vinyldiazo acetates and pyridine derivatives.

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7

Hayford, A., and J. Kaloko Jr. "Synthesis of Indolizine Derivatives by Electrocyclization." Synfacts 2006, no. 01 (2005): 0025. http://dx.doi.org/10.1055/s-2005-921691.

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8

Coffinier, Didier, Laurent El Kaim, and Laurence Grimaud. "Nef-Perkow Access to Indolizine Derivatives." Synlett 2010, no. 16 (2010): 2474–76. http://dx.doi.org/10.1055/s-0030-1258569.

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9

Dohmen, Christoph, Heiko Ihmels, Rouven Kreienmeier, and Brian O. Patrick. "Synthesis of a crystallochromic indolizine dye by a base- and catalyst-free photochemical route." Chemical Communications 55, no. 74 (2019): 11071–74. http://dx.doi.org/10.1039/c9cc04730a.

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Irradiation of 2-benzoyl-N-benzylpyridinium derivatives and dimethyl acetylene dicarboxylate resulted in the formation of inolizine derivatives, one which was found to be the first example of a crystallochromic indolizine.

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10

Wang, Yefei, Zhen Yang, Fengtao Zhan, et al. "Indolizine quaternary ammonium salt inhibitors part II: a reinvestigation of an old-fashioned strong acid corrosion inhibitor phenacyl quinolinium bromide and its indolizine derivative." New Journal of Chemistry 42, no. 15 (2018): 12977–89. http://dx.doi.org/10.1039/c8nj02505c.

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11

Sarkar, Rajib, Tandrima Chaudhuri, Animesh Karmakar та Chhanda Mukhopadhyay. "Synthesis and photophysics of selective functionalized π-conjugated, blue light emitting, highly fluorescent C7-imidazo indolizine derivatives". Organic & Biomolecular Chemistry 13, № 48 (2015): 11674–86. http://dx.doi.org/10.1039/c5ob01646k.

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12

Liu, Ren-Rong, Zheng-Yi Cai, Chuan-Jun Lu, et al. "Indolizine synthesis via Cu-catalyzed cyclization of 2-(2-enynyl)pyridines with nucleophiles." Organic Chemistry Frontiers 2, no. 3 (2015): 226–30. http://dx.doi.org/10.1039/c4qo00336e.

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13

MATSUDA, YOSHIRO, YOSHINORI TOMINAGA, YASUSHI TAJIMA, HIROYOSHI AWAYA, KEIJI KURATA, and HIROMI GOTOU. "Studies on Indolizine Derivatives. VII. : Syntheses of Cyclazinone Derivatives." YAKUGAKU ZASSHI 106, no. 12 (1986): 1098–107. http://dx.doi.org/10.1248/yakushi1947.106.12_1098.

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14

Kakehi, Akikazu, Suketaka Ito, Shin-ichi Matsumoto, and Yuichiro Morimoto. "Regiospecific Formations of Thieno[3,2-a]indolizine and Thieno[2,3-b]indolizine Derivatives." Chemistry Letters 16, no. 10 (1987): 2043–46. http://dx.doi.org/10.1246/cl.1987.2043.

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15

Browne, EJ. "Synthesis of 1H-[1]Benzothieno[3,2-d]azonine and [1]Benzothieno[3,2-d]azecine Derivatives." Australian Journal of Chemistry 38, no. 5 (1985): 765. http://dx.doi.org/10.1071/ch9850765.

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Derivatives of two new [1] benzothieno medium-ring heterocyclic systems have been prepared by ring degradation using cyanogen bromide-induced solvolysis of tetracyclic precursors. Reaction of a hexahydro -[1] benzothieno [3,2-g] indolizine (4a) and a hexahydro-2H-[1] benzo-thieno [2,3-a] quinolizine (4b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded the hexahydro-1H-[1] benzothieno [3,2-d] azonines (5a) and (6a) and the octahydro -[1] benzothieno [3,2-d] azecines (5b) and (6b), respectively. Functional group interconversions of these medium-ring systems are desc

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16

V, Sharma, Sharma PC, and Kumar V. "INDOLIZINE DERIVATIVES AS PHOSPHODIESTERASE IV INHIBITORS: DEVELOPMENT AND VALIDATION OF PHARMACOPHORE MODELS." Bulletin of Pharmaceutical Research 6, no. 2 (2016): 68–73. http://dx.doi.org/10.21276/bpr.2016.6.2.5.

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17

Kakehi, A., K. Kitajima, S. Ito, and N. Takusagawa. "Structures of furo[2,3-b]indolizine derivatives." Acta Crystallographica Section C Crystal Structure Communications 49, no. 3 (1993): 604–7. http://dx.doi.org/10.1107/s0108270192010205.

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18

BONNAUD, B., D. BIGG, and J. F. PATOISEAU. "ChemInform Abstract: Synthesis of Novel Indolizine Derivatives." ChemInform 23, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199220160.

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19

Dong, Shanliang, Jingjing Huang, Hongkai Sha, Lihua Qiu, Wenhao Hu, and Xinfang Xu. "Copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazoacetates and pyridines: access to polycyclic indolizines." Organic & Biomolecular Chemistry 18, no. 10 (2020): 1926–32. http://dx.doi.org/10.1039/d0ob00222d.

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A copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazo compounds with pyridines, which affords polycyclic fused indolizine derivatives with broad substrate generality, has been reported.

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20

Liu, Ruixing, Qiang Wang, Yin Wei, and Min Shi. "Synthesis of indolizine derivatives containing eight-membered rings via a gold-catalyzed two-fold hydroarylation of diynes." Chemical Communications 54, no. 10 (2018): 1225–28. http://dx.doi.org/10.1039/c7cc09250d.

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21

Su, Kexin, Xin Guo, Liangwei Zhu, Yafeng Liu, Yixuan Lu, and Baohua Chen. "Indolizine synthesis via radical cyclization and demethylation of sulfoxonium ylides and 2-(pyridin-2-yl)acetate derivatives." Organic Chemistry Frontiers 8, no. 15 (2021): 4177–82. http://dx.doi.org/10.1039/d1qo00550b.

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A novel radical cross-coupling/cyclization of 2-(pyridin-2-yl)acetate derivatives and sulfoxonium ylides is developed, which provides a straightforward access to structurally diverse methylthio-substituted indolizine.

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22

Atar, Amol Balu, Jongmin Kang, and Arvind H. Jadhav. "A [bmim]Cl-promoted domino protocol using an isocyanide-based [4+1]-cycloaddition reaction for the synthesis of diversely functionalized 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitriles under solvent-free conditions." New Journal of Chemistry 44, no. 8 (2020): 3241–48. http://dx.doi.org/10.1039/c9nj05738b.

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A room temperature-based ionic liquid [bmim]Cl-catalyzed multicomponent coupling strategy for the synthesis of 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitrile derivatives under mild conditions is shown.

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23

Kulandai Raj, Antony Sekar, Kuo-Chen Tan, Liang-Yu Chen, Mu-Jeng Cheng та Rai-Shung Liu. "Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles to form indolizine derivatives via an Au-π-allene intermediate". Chemical Science 10, № 26 (2019): 6437–42. http://dx.doi.org/10.1039/c9sc00735k.

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Gold-catalyzed bicyclic annulations of 4-methoxy-1,2-dienyl-5-ynes with isoxazoles afford indolizine derivatives; the reaction mechanism involves alkyne attack on a gold π-allene to yield a vinyl gold carbene.

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24

Yang, Jie, Yifan Zhu, Anfernee Kai-Wing Tse, et al. "Synthesis and study of Au(iii)–indolizine derivatives: turn-on luminescence by photo-induced controlled release." Chemical Communications 55, no. 31 (2019): 4471–74. http://dx.doi.org/10.1039/c8cc10177a.

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25

Dawood, Kamal M., Eman A. Ragab, and Sanaa N. Mohamed. "Synthesis of Some New Indolizine and Pyrrolo[1,2-a]quinoline Derivatives via Nitrogen Ylides." Zeitschrift für Naturforschung B 64, no. 4 (2009): 434–38. http://dx.doi.org/10.1515/znb-2009-0413.

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Pyridine and quinoline react with 3-bromoacetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile (2) in dry benzene to give the corresponding pyridinium and quinolinium salts 3 and 9. The latter salts undergo [3+2] 1,3-dipolar cycloaddition with some acetylene and ethylene derivatives to give the corresponding indolizine and pyrrolo[1,2-a]quinoline derivatives

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26

Bloch, Witold M., Stephanie M. Derwent-Smith, Fatiah Issa, Jonathan C. Morris, Louis M. Rendina, and Christopher J. Sumby. "Fused pyrazino[2,3-b]indolizine and indolizino[2,3-b]quinoxaline derivatives; synthesis, structures, and properties." Tetrahedron 67, no. 48 (2011): 9368–75. http://dx.doi.org/10.1016/j.tet.2011.09.133.

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27

Yang, Zhen, Yefei Wang, Fengtao Zhan, et al. "Indolizine quaternary ammonium salt inhibitors, part III: insights into the highly effective low-toxicity acid corrosion inhibitor – synthesis and protection performance." New Journal of Chemistry 43, no. 47 (2019): 18461–75. http://dx.doi.org/10.1039/c9nj04203b.

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Three indolizine derivatives (Di-BQC, QM-DiBQC, PyM-DiBQC) were prepared facilely in high yield via 1,3-dipolar cycloaddition. These compounds exhibit good inhibition for steel in concentrated acid without the synergism of propargyl alcohol (PA).

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28

Zhou, Bixiang, Mengjie Guo, Qingjie Pan та ін. "Rhodium-catalyzed annulation of pyrrole substituted BODIPYs with alkynes to access π-extended polycyclic heteroaromatic molecules and NIR absorption". Organic Chemistry Frontiers 8, № 5 (2021): 868–75. http://dx.doi.org/10.1039/d0qo01625j.

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A series of π-extended BODIPY derivatives fused with an indolizine scaffold were prepared smoothly via rhodium-catalyzed C–H functionalization/annulation. These fluorophores show significantly red-shifted absorption, reaching to the near infrared (NIR) region.

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29

Dawood, Kamal M., and Ashraf A. Abbas. "Inhibitory activities of indolizine derivatives: a patent review." Expert Opinion on Therapeutic Patents 30, no. 9 (2020): 695–714. http://dx.doi.org/10.1080/13543776.2020.1798402.

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30

Molina, P., P. M. Fresneda, and M. C. Lájara. "Synthesis using pyridinium anhydrobases, preparation of indolizine derivatives." Journal of Heterocyclic Chemistry 22, no. 1 (1985): 113–19. http://dx.doi.org/10.1002/jhet.5570220129.

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31

Coffinier, Didier, Laurent El Kaim, and Laurence Grimaud. "ChemInform Abstract: Nef-Perkow Access to Indolizine Derivatives." ChemInform 42, no. 6 (2011): no. http://dx.doi.org/10.1002/chin.201106174.

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32

MAHON, J., L. K. MEHTA, R. W. MIDDLETON, J. PARRICK, and H. K. RAMI. "ChemInform Abstract: Some Indolizine Derivatives Useful as Fluorophores." ChemInform 24, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199311049.

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33

Yuan, Yu-Chang, Tian-Zhen Liu, and Bao-Xiang Zhao. "Metal-Free Catalyzed Synthesis of Fluorescent Indolizine Derivatives." Journal of Organic Chemistry 86, no. 18 (2021): 12737–44. http://dx.doi.org/10.1021/acs.joc.1c01292.

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34

Uppar, Vijayakumar, Sandeep Chandrashekharappa, Mahendra K. Mohan, et al. "Synthesis and characterization of indolizine and 5,6-benzo-fused indolizine derivatives with their pharmacological applications." Chemical Data Collections 29 (October 2020): 100524. http://dx.doi.org/10.1016/j.cdc.2020.100524.

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35

Pal, Kumar Bhaskar, Mukul Mahanti, Xiaoli Huang, et al. "Quinoline–galactose hybrids bind selectively with high affinity to a galectin-8 N-terminal domain." Organic & Biomolecular Chemistry 16, no. 34 (2018): 6295–305. http://dx.doi.org/10.1039/c8ob01354c.

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Straightforward methods to incorporate quinoline, indolizine, and coumarin structures into galactoside derivatives and evaluation of binding affinities towards a panel of human galectins lead to the discovery of selective and potent inhibitors of the N-terminal domain of galectin-8.

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36

Szefler, Beata, Przemysław Czeleń, and Mircea V. Diudea. "Docking of Indolizine Derivatives on Cube Rhombellane Functionalized Homeomorphs." Studia Universitatis Babeș-Bolyai Chemia 63, no. 2 (2018): 7–18. http://dx.doi.org/10.24193/subbchem.2018.2.01.

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37

Xu, Tongyu, and Howard Alper. "Synthesis of Indolizine Derivatives by Pd-Catalyzed Oxidative Carbonylation." Organic Letters 17, no. 18 (2015): 4526–29. http://dx.doi.org/10.1021/acs.orglett.5b02220.

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38

Huang, Wenlin, Tao Zuo, Xiao Luo, et al. "Indolizine Derivatives as HIV-1 VIF-ElonginC Interaction Inhibitors." Chemical Biology & Drug Design 81, no. 6 (2013): 730–41. http://dx.doi.org/10.1111/cbdd.12119.

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39

KAKEHI, A., K. KITAJIMA, S. ITO, and N. TAKUSAGAWA. "ChemInform Abstract: Structures of Furo(2,3-b)indolizine Derivatives." ChemInform 24, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199327055.

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40

Stefancich, Giorgio, Federico Corelli, Silvio Massa, Romano Silvestri, and Roberto Di Santo. "Heterocyclic systems.VIISynthesis of 1H-pyrazolo[3,4-e]indolizine derivatives." Journal of Heterocyclic Chemistry 24, no. 4 (1987): 1199–202. http://dx.doi.org/10.1002/jhet.5570240451.

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41

Zhang, Xue-chun, and Wei-yuan Huang. "A One-Step Approach to 1-(Fluoroalkyl)indolizine Derivatives." Synthesis 1999, no. 1 (1999): 51–54. http://dx.doi.org/10.1055/s-1999-3675.

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42

Kakehi, Akikazu, Suketaka Ito, and Susumu Hatanaka. "First Syntheses of 1,4-Thiazino[3,4,5-cd]indolizine Derivatives." Chemistry Letters 18, no. 12 (1989): 2229–32. http://dx.doi.org/10.1246/cl.1989.2229.

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43

Weide, Timo, Lars Arve, Heino Prinz, Herbert Waldmann, and Horst Kessler. "3-Substituted indolizine-1-carbonitrile derivatives as phosphatase inhibitors." Bioorganic & Medicinal Chemistry Letters 16, no. 1 (2006): 59–63. http://dx.doi.org/10.1016/j.bmcl.2005.09.051.

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44

Lu, Jiamin, Meifang Wang, Ruigang Xu, et al. "Iridium Catalysed Asymmetric Allylic Substitution Reaction of Indolizine Derivatives." Asian Journal of Organic Chemistry 10, no. 6 (2021): 1500–1507. http://dx.doi.org/10.1002/ajoc.202100171.

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45

Bloch, Witold M., Stephanie M. Derwent-Smith, Fatiah Issa, Jonathan C. Morris, Louis M. Rendina, and Christopher J. Sumby. "ChemInform Abstract: Fused Pyrazino[2,3-b]indolizine and Indolizino[2,3-b]quinoxaline Derivatives: Synthesis, Structures, and Properties." ChemInform 43, no. 31 (2012): no. http://dx.doi.org/10.1002/chin.201231183.

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46

Soare, Maria-Laura, Eleonora-Mihaela Ungureanu, Emilian Georgescu, and Liviu Birzan. "Synthesis and electrochemical characterization of substituted indolizine carboxylates." Journal of the Serbian Chemical Society 78, no. 6 (2013): 827–38. http://dx.doi.org/10.2298/jsc120810117s.

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This work is devoted to the synthesis and characterization of new indolizine derivatives. Particular attention was paid to the electrochemical investigations by cyclic voltammetry and differential pulse voltammetry. The redox processes for each compound were established, analyzed and assessed to the particular functional groups at which they take place. This assessment was based on detailed comparison between the electrochemical behaviour of the compounds, similarities in their structure, as well as substituent effects.

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47

Belguedj, Roumaissa, Sofiane Bouacida, Hocine Merazig, Ali Belfaitah, and Abdelmalek Bouraiou. "1-(2′-Benzimidazolylmethyl)-pyridinium ylide in the one-pot synthesis of indolizine and benzimidazo[1,2-a]pyridine derivatives." Zeitschrift für Naturforschung B 70, no. 8 (2015): 555–61. http://dx.doi.org/10.1515/znb-2015-0016.

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AbstractFour indolizine derivatives were obtained via 1,3-dipolar cycloaddition reaction of 1-(2′-benzimidazolylmethyl)pyridinium ylide with various electron-deficient alkynes. The reaction of this pyridinium N-ylide with dimethyl maleate gave an unexpected methyl 1-oxo-benzimidazo[1,2-a]pyridine-3-carboxylate. The structures of all reported compounds have been examined by X-ray crystallography and NMR spectroscopy.

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48

Georgescu, Emilian, Florentina Georgescu, Constantin Draghici, Petru Filip, and Florea Dumitrascu. "New Substituted Indolizines by 1,3-Dipolar Cycloaddition Reactions I. 7-tert-Butylindolizines." Revista de Chimie 59, no. 3 (2008): 269–72. http://dx.doi.org/10.37358/rc.08.3.1746.

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The new indolizine derivatives 6a-h containing a tert-butyl group grafted on the pyridinic ring were obtained by reaction of N-phenacylpyridinium bromides 3 with ethyl propiolate as acetylenic dipolarophile in medium of 1,2-epoxybutane at reflux. Structural proof for the compounds was provided by elemental analysis and NMR spectroscopy, including COSY and HETCOR experiments.

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49

Rečnik, Simon, Anton Meden, Branko Stanovnik, and Jurij Svete. "Ring Contractions of 3-Azido-4H-quinolizin-4-ones and 3-Azido-4H-azino[1,2 - x]pyrimidin-4-ones: a Novel Approach to 3-Aminoindolizines and their Aza Analogues." Australian Journal of Chemistry 61, no. 2 (2008): 107. http://dx.doi.org/10.1071/ch07318.

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Thermal transformations of 3-azido-4H-quinolizin-4-ones 4a,b and 3-azido-4H-azino[1,2–x]pyrimidin-4-ones 4c,d, available from the corresponding heteroarylamines 2a–d, were studied. The reaction products were mostly dependent on the solvent. Thus, heating of 3-azido-1-cyano-4H-quinolizin-4-one (4a) in toluene afforded 2-(pyridin-2-yl)fumaronitrile 5a, whereas 3-amino-1-cyano-4H-quinolizin-4-one (8) was obtained on treatment of 4a in a mixture of toluene and trifluoroacetic anhydride. However, heating of 4a in acetic anhydride and in acetic acid resulted in a ring contraction to produce 3-(diace

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50

Olejníková. "Antimicrobial and Antimutagenic Properties of Newly Synthesized Derivatives of Indolizine." Scientia Pharmaceutica 77, no. 1 (2009): 216. http://dx.doi.org/10.3797/scipharm.oephg.21.po-17.

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