European Journal of Organic Chemistry
10.1002/ejoc.201900526
FULL PAPER
[
[
12] D. N. Kommi, P. S. Jadhavar, D. Kumar, A. K. Chakraborti, Green
Chem. 2013, 15, 798–810.
We thank Dr Andrej Batsanov of Durham University for solving
the X-ray structures of compound 15 and 16.
13] E. C. Creencia, M. Kosaka, T. Muramatsu, M. Kobayashi, T. Iizuka, T.
Horaguchi, J. Het. Chem. 2009, 46, 1309–1317.
Keywords: Flow chemistry, heterocycles, photochemistry,
[14] a) Z. Wróbel, A. Kwast, Synlett 2007, 1525–1528; b) Z. Wróbel, K.
Plichta, A. Kwast, Tetrahedron 2017, 73, 3147–3152.
pyocyanin, natural product
[
15] J. D. Winkler, B. M. Twenter, T. Gendrineau, Heterocycles 2012, 84,
345–1353.
16] a) K. Seth, S. R. Roy, A. K. Chakraborti, Chem. Commun. 2016, 52,
22–925; b) K. Seth, S. R. Roy, A. Kumar, A. K. Chakraborti, Catal. Sci.
1
[
[
[
1]
2]
3]
D. Nathwani, G. Raman, K. Sulham, M. Gavaghan, V. Menon,
Antimicrobial Resistance and Infection Control 2014, 3, 1–16.
[
9
J. W. Newman, R. V. Floyd, J. L. Fothergill, FEMS Microbiol. Lett., 2017,
Technol., 2016, 6, 2892–2896.
364(15), fnx124 (1–11).
[
17] a) X. Ni, M. R. Mackley, A. P. Harvey, P. Stonestreet, M. H. I. Baird, N.
V. Rama Rao, Trans IChemE 2003, 81, 373–383; b) J. Sedelmeier, S.
V. Ley, I. R. Baxendale, M. Baumann, Org. Lett. 2010, 12, 3618–3621;
c) D. L. Browne, B. J. Deadman, R. Ashe, I. R. Baxendale, S. V. Ley,
Org. Proc. Res. Dev. 2011, 15, 693–697; d) T. Noël, J. R. Naber, R. L.
Hartman, J. P. McMullen, K. F. Jensen, S. L. Buchwald, Chem. Sci.,
a) Y. Q. O'Malley, K. J. Reszka, D. R. Spitz, G. M. Denning, B. E.
Britigan, Am. J. Physiol. Lung Cell. Mol. Phys. 2004, 287, L94–L103; b)
G. W. Lau, H. M. Ran, F. S. Kong, D. J. Hassett, D. Mavrodi, Infect.
Immun. 2004, 72, 4275–4278; c) G. W. Lau, D. J. Hassett, H. Ran, F.
Kong, Trends Mol. Med. 2004, 10, 599–606; d) E. Kipnis, T. Sawa, J.
Wiener-Kronish, Med. Maladies Infect. 2006, 36, 78–91; e) B.
Morkunas, W. R. J. D. Galloway, M. Wright, B. M. Ibbeson, J. T.
Hodgkinson, K. M. O'Connell, N. Bartolucci, M. D. Valle, M. Welch, D. R.
Spring, Org. Biomol. Chem. 2012, 10, 8452–8464; f) N. V. Borrero, F.
Bai, C. Perez, B. Q. Duong, J. R. Rocca, S. Jin, R. W. Huigens, Org.
Biomol. Chem. 2014, 12, 881–886; g) C. Pastells, N. Pascual, F.
Sanchez-Baeza, M.-P. Marco, Anal. Chem. 2016, 88, 1631–1638.
a) A. Price-Whelan, L. E. P. Dietrich and D. K. Newman, Nat. Chem.
Biol., 2006, 2, 71–78; b) Z. A. Machan, T. L. Pitt, W. White, D. Watson,
G. W. Taylor, P. J. Cole and R. Wilson, J. Med. Microbiol., 1991, 34,
2011, 2, 287–290; e) P. Koos, D. L. Browne, S. V. Ley, Green Process.
Synth. 2012, 1, 11–18; f) R. L. Hartman, Org. Proc. Res. Dev., 2012,
16(5), 870–887; g) K. Wu, S. Kuhn Chimica Oggi - Chemistry Today
2014, 32, 62–66; h) P. Filipponi, A. Gioiello, I. R. Baxendale, Org. Proc.
Res. Dev. 2016, 20, 371–375; i) A. A. Lapkin, K. Loponov, G.
Tomaiuolo, S. Guido Sustainable Flow Chemistry: Methods and
Applications (Ed: L. Vaccaro) in Solids in Continuous Flow Reactors for
Specialty and Pharmaceutical Syntheses, WILEY‐VCH Verlag GmbH
[4]
[
213–217.
[
[
5]
6]
a) C. Jacob, V. Jamier, L. A. Ba, Curr. Opin. Chem. Biol. 2011, 15,
19] a) C. W. Jefford, J.-C. Rossier, S. Kohmoto, J. Boukouvalas, J. Chem.
Soc., Chem. Commun., 1984, 1496–1497; b) S. P. Zingg, Michael E.
Sigman, Photochem. Photobiol., 1993, 57, 453–459; c) M. Klaper, P.
Wessig, T. Linker, Chem. Commun., 2016, 52, 1210–1213.
1
49–155; b) Z. Wróbel, K. Plichta, A. Kwast, Tetrahedron 2017, 73,
147–3152.
3
a) R. Preetha, S. Jose, S. Prathapan, K. K. Vijayan, N. S. Jayaprakash,
R. Philip, I. S. B. Singh, Aquacult. Res. 2010, 41, 1452–1461; b) P.
Priyaja, P. Jayesh, R. Philip, I. S. Bright Singh, Cytotechnology 2016,
[
20] a) K. Kitahara, H, Nishi, J. Het. Chem. 1988, 25, 1063–1065; b) E.
Berni, C. Dolain, B. Kauffmann, J.-M. Léger, C. Zhan, I. Huc, J. Org.
Chem., 2008, 73, 2687–2694.
68, 143–155; c) A. Priyaja in Pyocyanin (5-methyl-1-hydroxyphenazine)
produced by Pseudomonas aeruginosa as antagonist to vibrios in
aquaculture: Overexpression, downstream process and toxicity, Ph.D
thesis 2013. India: Cochin University of Science and Technology; d) P.
Priyaja, P. Jayesh, N. Correya, B. Sreelakshmi, N. Sudheer, R. Philip, I.
[
21] a) H. McIlwain, J. Chem. Soc. 1937, 1704–1711; b) D. N. Bailey, D. K.
Roe, D. M. Hercules, J. Am. Soc. 1968, 90, 6291–6297; c) S. Wake, H.
Inoue, Y. Otsuji, E. Imoto, Tetrahedron Lett. 1970, 11, 2415–2418; d) M.
E. Flood, R. B. Herbert, F. G. Holliman J. Chem. Soc. D, 1970, 1514–
1515.
[
[
7]
8]
aeruginosa, ≥98% (HPLC). March 2019.
[
22] S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D.
A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, S. J. J. Talyor, Chem.
Soc., Perkin Trans. 1 2000, 23, 3815–4196.
a) G. S. Byng, D. C. Eustice, R. A. Jensen, J. Bacteriol., 1979, 138(3),
8
46–852; b) R. Maier, G. Soberon-Chavez,
Biotechnol. 2000, 54, 625–633; c) J. B. Laursen, J. Nielsen, Chem. Rev.
004, 104, 1663-1686; d) M. Muller, N. D. Merrett, Antimicrob. Agents
Appl.
Microbiol.
[23] D. L. Vivian, Nature, 1956, 178, 753–.
[24] H. Rao, Y. Jin, H. Fu, Y. Jiang, Y. Zhao, Chem. Euro. J. 2006, 12,
2
3636–3646.
Chemother. 2014, 58, 5492–5499; e) M. Z. El-Fouly, A. M. Sharaf, A. A.
M. Shahin, H. A. El-Bialy, A. M. A. Omara, J. Radiat. Res. Appl. Sci.,
[
25] a) F. Wrede, E. Strack, Z. Physiol. Chem. 1924, 140, 1–15; b) K. Ohfuji,
N. Sato, N. Hamada-Sato, T. Kobayashi, C. Imada, H. Okuma, E.
Watanabe, Biosens. Bioelectron. 2004, 19, 1237–1244.
2015, 8, 36–48; f) P. Devnath, M. K. Uddin, F. Ahamed, M. T. Hossain,
M. A. Manchur, Int. Res. J. Bio. Sci. 2017, 6, 1–9.
[26] C. H. Issidorides, M. A. Atfah, J. J. Sabounji, A. R. Sidani, M. J.
Haddadin, Tetrahedron 1978, 34, 217–221.
[9]
a) F. Kehrmann, E. Havas, Euro. J. Inorg. Chem. 1913, 46, 341–352; b)
F. Wrede, E. Strack, Hoppe-Seyler’s Zeitschrift für physiologische
Chemie 1924, 140, 1–15; c) F. Wrede, E. Strack, Ber. Dtsch. Chem.
Ges. (A and B Series) 1929, 62, 2051–2057; d) A. R. Surrey, Org.
Synth. 1946, 26, 86–88; e) M. Knight, P. E. Hartman, Z. Hartman, V. M.
Young, Anal. Biochem. 1979, 95, 19–23; e) R. Cheluvappa, MethodsX
2014, 1, 67–73.
[
10] a) M. Baumann, I. R. Baxendale, S. V. Ley, SynLett, 2008, 2111–2114;
b) J. T. Hodgkinson, W. R. J. D. Galloway, S. Saraf, I. R. Baxendale, S.
V. Ley, M. Ladlow, M. Welch, D. R. Spring, Org. Biomol. Chem. 2011, 9,
57–61; c) J. Zak, D. Ron, E. Riva, H. P. Harding, B. C. S. Cross, I. R.
Baxendale, Chem. Euro. J. 2012, 18, 9901–9910; d) M. Baumann, I. R.
Baxendale, React. Chem. Eng. 2016, 1, 147–150; e) M. O. Kitching, O.
E. Dixon, M. Baumann, I. R. Baxendale, Euro. J. Org. Chem. 2017,
6540–6553; f) M. Baumann, I. R. Baxendale, F. Deplante, Beilstein J.
Org. Chem. 2017, 13, 2549–2560; g) L. K. Smith, I. R. Baxendale,
React. Chem. Eng. 2018, 3, 722–732.
[
11] Phenazine CAS: 92-82-0; Aldrich P13207. Alfa Aesar A15770. Tokyo
Chemical Industry UK Ltd P0082.
This article is protected by copyright. All rights reserved.