Synthesis 2021; 53(04): 713-722
DOI: 10.1055/s-0040-1707293
paper

A Three-Step Synthesis of 1,7-Diazaperylene and Derivatives

,
Susanne Reichherzer
,
Peter Mayer
,
Kurt Polborn


Abstract

1,7-Diazaperylene and various derivatives were synthesised in an upscaleable route from 1,5-diaminoanthraquinone and its Meerwein­ reaction with acrylonitrile and subsequent cyclisation with ammonia. The application of tert-butyl alcohol as the solvent led to a significant improvement in the Meerwein reaction.

Supporting Information



Publication History

Received: 30 May 2020

Accepted after revision: 31 August 2020

Publication Date:
27 October 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Markiewicz JT, Wudl F. ACS Appl. Mater. Interfaces 2015; 7: 28063
  • 2 Mishra A, Bäuerle P. Angew. Chem. Int. Ed. 2012; 51: 2020
  • 3 Walker B, Kim C, Nguyen T.-Q. Chem. Mater. 2011; 23: 470
  • 4 Lungenschmied C, Dennler G, Neugebauer H, Sariciftci SN, Glatthaar M, Meyer T, Meyer A. Sol. Energy Mater. Sol. Cells 2007; 91: 379 ; Chem. Abstr. 2007, AN96917
  • 5 Kaltenbrunner M, White S, Glowacki ED, Sekitani T, Someya T, Sariciftci NS, Bauer S. Nat. Commun. 2012; 3: 1772
  • 6 Naumann C, Langhals H. Chem. Ber. 1990; 123: 1881
  • 7 Tucker SA, Acree WE. Jr, Tanga MJ, Tokita S, Hiruta K, Langhals H. Appl. Spectrosc. 1992; 46: 229
  • 8 Tucker SA, Darmodjo H, Acree WE. Jr, Zander M, Meister EC, Tanga MJ, Tokita S. Appl. Spectrosc. 1992; 46: 1630
  • 9 Tucker SA, Acree WE. Jr, Upton C. Appl. Spectrosc. 1993; 47: 201
  • 10 Johansson LB.-Å, Karolin J, Langhals H, Reichherzer S, von Füner N, Polborn K. J. Chem. Soc., Faraday Trans. 1993; 89: 49
  • 11 Sander T, Löhmannsröben H.-G, Langhals H. J. Photochem. Photobiol., A: Chem. 1995; 86: 103
  • 12 Cyranski M, Krygowski TM. Tetrahedron 1996; 52: 13795
  • 13 Habenicht A, Hjelm J, Mukhtar E, Bergstrom F, Johansson LB.-Å. Chem. Phys. Lett. 2002; 354: 367
  • 14 Ryderfors L, Mukhtar E, Johansson LB.-Å. J. Phys. Chem. A 2008; 112: 5794
  • 15 Wong ZC, Fan WY, Chwee TS, Sullivan MB. Phys. Chem. Chem. Phys. 2017; 19: 21046
  • 16 Xiong T, Wlodarczyk R, Saalfrank P. Chem. Phys. 2018; 515: 728
  • 17 Ropp GA, Coyner EC. Org. Synth. 1951; 31: 80
  • 18 Heinrich MR. Chem. Eur. J. 2009; 15: 820
  • 19 Baranov DS, Uvarov MN, Kazantsev MS, Mostovich EA, Glebov EM, Gatilov YV, Kulik LV. Dyes Pigm. 2017; 136: 707
  • 20 Scholl R, Hass S, Meyer HK. Ber. Dtsch. Chem. Ges. 1929; 62B: 107 ; Chem. Abstr. 1929, 23, 22871
  • 21 Novikov AN, Slyusarchuk VT, Chaplygina GA. Izv. Tomsk. Politekhn. In-ta 1976; 274: 7 ; Chem. Abstr. 1978, 88, 62201
  • 22 Perraudin R. Cuivre, Laitons, Alliages (Geneva) 1958; 43: 33; Chem. Abstr. 1961, 55, 83852
  • 23 Fritz H, Rihs G, Sutter P, Weis CD. J. Heterocycl. Chem. 1981; 18: 1571
  • 24 Krapcho AP, Shaw JK. J. Org. Chem. 1983; 48: 3341
  • 25 Shilstone GN, Zannoni C, Veracini CA. Liq. Cryst. 1989; 6: 303
  • 26 Donaldson DM, Robertson JM, White FR. S, White JJ. Proc. R. Soc. A 1953; 220: 311
  • 27 Camerman A, Trotter J. Proc. R. Soc. A 1964; 279: 129
  • 28 Botoshansky M, Herbstein FH, Kapon M. Helv. Chim. Acta 2003; 86: 1113
  • 29 CCDC 1999505 (1), CCDC 1999506 (5a), CCDC 1999507 (5b), CCDC 1999508 (5d), and CCDC 1999509 (5e) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.