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Christmann, M. et al.: 2020 Science of Synthesis: Knowledge Updates 2020/2 DOI: 10.1055/sos-SD-116-01265
Knowledge Updates 2020/2

16.16.5 Phenazines (Update 2020)

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Buch

Herausgeber: Christmann, M.; Huang, Z.; Joule, J. A.; Li, C.-J.; Li, J.; Marschner, C.; Petersson, E. J.; Reißig, H.-U.; Schaumann, E.; Terent'ev, A. 

Autoren: Ambhaikar, N.; Campagne, J.-M.; Celik, I.; Dembitsky, V.; Graham, M.; Holzschneider, K.; Jaschinski, M.; Kipke, W.; Kirsch, S.; Kunz, K.; Leclerc, E.; Li, G.; Li, Z.; Makow, J.; Müller, T.; Ochoa, C. I.; Ramirez y Medina, I.-M. .; Rayner, C. M.; Staubitz, A.; Sun, X.-L.; Szostak, M.; Tambar, U. K.; Tian, T.; Tong, M.; Wang, X.-Y.; Yaremenko, I.; Yoshikai, N.

Titel: Knowledge Updates 2020/2

Print ISBN: 9783132435612; Online ISBN: 9783132435636; Buch-DOI: 10.1055/b000000103

1st edition © 2020 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Knowledge Updates



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G.; Nevado, C.; Trost, B. M.; You, S.

Typ: Mehrbändiges Werk

Auch verfügbar auf
 

Abstract

Phenazines are an interesting class of nitrogen-containing heterocycles present in many natural products. This update describes the construction of phenazines through some newer practical synthetic methods that have been reported since the first review on phenazines in Science of Synthesis (Section 16.16). For the most part, standard ways of synthesizing phenazine and its derivatives have employed traditional approaches or their variations along the lines of the Wohl–Aue reaction and the Beirut reaction. The current account focuses on modern synthetic tools to construct the phenazine core and includes some of the newer approaches, with recent key methods that have been developed between 2004 and 2019.

Schlüsselwörter

phenazines - phenazine N-oxides - electrochemical reduction - C-H activation - oxidative coupling - Fischer carbenes - cyclization - quinoxalines
 
  • 1 Beifuss, U., Tietze, M.. Top. Curr. Chem.. 2005; 244: 77
    Google Scholar
  • 2 Laursen, J. B., Nielsen, J.. Chem. Rev.. 2004; 104: 1663
    Google Scholar
  • 3 Turner, J. M., Messenger, A. J.. Adv. Microb. Physiol.. 1986; 27: 211
    Google Scholar
  • 4 Pierson, III L. S., Pierson, E. A.. Appl. Microbiol. Biotechnol.. 2010; 86: 1659
    Google Scholar
  • 5 Borrero, N. V., Bai, F., Perez, C., Duong, B. Q., Rocca, J. R., Jin, S., Huigens, III R. W.. Org. Biomol. Chem.. 2014; 12: 881
    Google Scholar
  • 6 Sheng, J., He, R., Xue, J., Wu, C., Qiao, J., Chen, C.. Org. Lett.. 2018; 20: 4458
    Google Scholar
  • 7 Wang, C., Wang, J., Li, P.-Z., Gao, J., Tan, S. Y., Xiong, W.-W., Hu, B., Lee, P. S., Zhao, Y., Zhang, Q.. Chem.–Asian J.. 2014; 9: 779
    Google Scholar
  • 8 Ogata, T., Yamamoto, Y., Wada, Y., Murakoshi, K., Kusaba, M., Nakashima, N., Ishida, A., Takamuku, S., Yanagida, S.. J. Phys. Chem.. 1995; 99: 11 916
    Google Scholar
  • 9 Gu, P.-Y., Zhao, Y., He, J.-H., Zhang, J., Wang, C., Xu, Q.-F., Lu, J.-M., Sun, X. W., Zhang, Q.. J. Org. Chem.. 2015; 80: 3030
    Google Scholar
  • 10 Shi, J., Chen, J., Chai, Z., Wang, H., Tang, R., Fan, K., Wu, M., Han, H., Qin, J., Peng, T., Li, Q., Li, Z.. J. Mater. Chem.. 2012; 22: 18 830
    Google Scholar
  • 11 Richard, C. A., Pan, Z., Parthasarathy, A., Arroyave, F. A., Estrada, L. A., Schanze, K. S., Reynolds, J. R.. J. Mater. Chem. A. 2014; 2: 9866
    Google Scholar
  • 12 Zhang, G., Zhang, H., Wang, X., Li, C., Huang, H., Yin, D.. Molecules. 2011; 16: 6985
    Google Scholar
  • 13 Browne, S. G., Hogerzeil, L. M.. Lepr. Rev.. 1962; 33: 6
    Google Scholar
  • 14 Van Rensburg, C. E. J., Van Staden, A. M., Anderson, R.. Cancer Research. 1993; 53: 318
    Google Scholar
  • 15 Yew, W. W., Chau, C. H.. Monaldi Arch. Chest Dis.. 1996; 51: 394
    Google Scholar
  • 16 Polson, M. I. J., Howell, S. L., Flood, A. H., Burrell, A. K., Blackman, A. G., Gordon, K. C.. Polyhedron. 2004; 23: 1427
    Google Scholar
  • 17 Kaafarani, B. R., Lucas, L. A., Wex, B., Jabbour, G. E.. Tetrahedron Lett.. 2007; 48: 5995
    Google Scholar
  • 21 Vivian, D. L., Hogart, R. M., Belkin, M.. J. Org. Chem.. 1961; 26: 112
    Google Scholar
  • 23 Pachter, I. J., Kloetzel, M. C.. J. Am. Chem. Soc.. 1952; 74: 971
    Google Scholar
  • 25 Guirado, A., Cerezo, A., Andreu, R., López Sánchez, J. I., Bautista, D.. Tetrahedron. 2004; 60: 6747
    Google Scholar
  • 26 De Buyck, L., Vanslembrouck, J., De Kimpe, N., Verhe, R., Schamp, N.. Bull. Soc. Chim. Belg.. 1984; 93: 913
    Google Scholar
  • 27 Koepf, M., Lee, S. H., Brennan, B. J., Méndez-Hernández, D. D., Batista, V. S., Brudvig, G. W., Crabtree, R. H.. J. Org. Chem.. 2015; 80: 9881
    Google Scholar
  • 29 Sheldon, R. A., Arends, I. W. C. E., ten Brink, G.-J., Dijksman, A.. Acc. Chem. Res.. 2002; 35: 774
    Google Scholar
  • 30 Punniyamurthy, T., Velusamy, S., Iqbal, J.. Chem. Rev.. 2005; 105: 2329
    Google Scholar
  • 32 Stahl, S. S.. Angew. Chem. Int. Ed.. 2004; 43: 3400
    Google Scholar
  • 33 Do, H.-Q., Daugulis, O.. J. Am. Chem. Soc.. 2007; 129: 12 404
    Google Scholar
  • 34 Chen, X., Hao, X.-S., Goodhue, C. E., Yu, J.-Q.. J. Am. Chem. Soc.. 2006; 128: 6790
    Google Scholar
  • 35 Do, H.-Q., Daugulis, O.. J. Am. Chem. Soc.. 2008; 130: 1128
    Google Scholar
  • 36 Borduas, N., Powell, D. A.. J. Org. Chem.. 2008; 73: 7822
    Google Scholar
  • 37 Monguchi, D., Fujiwara, T., Furukawa, H., Mori, A.. Org. Lett.. 2009; 11: 1607
    Google Scholar
  • 38 Zhao, L., Li, C.-J.. Angew. Chem. Int. Ed.. 2008; 47: 7075
    Google Scholar
  • 39 Strieter, E. R., Bhayana, B., Buchwald, S. L.. J. Am. Chem. Soc.. 2009; 131: 78
    Google Scholar
  • 40 Yotphan, S., Bergman, R. G., Ellman, J. A.. Org. Lett.. 2009; 11: 1511
    Google Scholar
  • 41 Ackermann, L., Potukuchi, H. K., Landsberg, D., Vicente, R.. Org. Lett.. 2008; 10: 3081
    Google Scholar
  • 43 Brasche, G., Buchwald, S. L.. Angew. Chem. Int. Ed.. 2008; 47: 1932
    Google Scholar
  • 45 Satoh, T., Miura, M.. Chem.–Eur. J.. 2010; 16: 11 212
    Google Scholar
  • 46 Wencel-Delord, J., Dröge, T., Liu, F., Glorius, F.. Chem. Soc. Rev.. 2011; 40: 4740
    Google Scholar
  • 47 Song, G., Wang, F., Li, X.. Chem. Soc. Rev.. 2012; 41: 3651
    Google Scholar
  • 48 Lian, Y., Hummel, J. R., Bergman, R. G., Ellman, J. A.. J. Am. Chem. Soc.. 2013; 135: 12 548
    Google Scholar
  • 49 Yu, B.-C., Shirai, Y., Tour, J. M.. Tetrahedron. 2006; 62: 10 303
    Google Scholar
  • 51 Bouffard, J., Swager, T. M.. Macromolecules. 2008; 41: 5559
    Google Scholar
  • 52 Balicki, R., Cybulski, M., Maciejewski, G.. Synth. Commun.. 2003; 33: 4137
    Google Scholar
  • 53 Roy, P., Ghorai, B. K.. Beilstein J. Org. Chem.. 2010; 6: 52
    Google Scholar
  • 54 Muci, A. R., Buchwald, S. L.. Top. Curr. Chem.. 2002; 219: 131
    Google Scholar
  • 55 Hartwig, J. F., Modern Arene Chemistry. Astruc, D.. Wiley VCH; Weinheim 2002. 107.
    Google Scholar
  • 56 Wolfe, J. P., Wagaw, S., Marcoux, J.-F., Buchwald, S. L.. Acc. Chem. Res.. 1998; 31: 805
    Google Scholar
  • 58 Tietze, M., Iglesias, A., Merisor, E., Conrad, J., Klaiber, I., Beifuss, U.. Org. Lett.. 2005; 7: 1549
    Google Scholar
  • 59 Abken, H.-J., Tietze, M., Brodersen, J., Bäumer, S., Beifuss, U., Deppenmeier, U.. J. Bacteriol.. 1998; 180: 2027
    Google Scholar
  • 60 Beifuss, U., Tietze, M., Bäumer, S., Deppenmeier, U.. Angew. Chem. Int. Ed.. 2000; 39: 2470
    Google Scholar
  • 61 Wróbel, Z., Plichta, K., Kwast, A.. Tetrahedron. 2017; 73: 3147
    Google Scholar
  • 62 Gao, Q., Liu, S., Wu, X., Wu, A.. Org. Lett.. 2014; 16: 4582
    Google Scholar
  • 63 He, Z., Li, H., Li, Z.. J. Org. Chem.. 2010; 75: 4636
    Google Scholar
  • 64 Fra, L., Millán, A., Souto, J. A., Muñiz, K.. Angew. Chem. Int. Ed.. 2014; 53: 7349
    Google Scholar
  • 65 Kumar, S., Mujahid, M., Verma, A. K.. Org. Biomol. Chem.. 2017; 15: 4686
    Google Scholar
  • 66 Laha, J. K., Tummalapalli, K. S. S., Gupta, A.. Org. Lett.. 2014; 16: 4392
    Google Scholar
  • 67 Laha, J. K., Tummalapalli, K. S. S., Gupta, A.. Eur. J. Org. Chem.. 2013; 8330
    Google Scholar
  • 68 Ishizumi, K., Mori, K., Inaba, S., Yamamoto, H.. Chem. Pharm. Bull.. 1975; 23: 2169
    Google Scholar
  • 69 Black, D. S. C., Rothnie, N. E.. Aust. J. Chem.. 1983; 36: 1149
    Google Scholar