Organic & Biomolecular Chemistry
Paper
6 A. Williams and I. T. Ibrahim, Chem. Rev., 1981, 81, 589–
pyridine amide: J. Bergman, R. Carlsson and S. Misztal,
636.
Acta Chem. Scand., 1976, 30, 853–862.
7 C. A. G. N. Montalbetti and V. Falque, Tetrahedron, 2005, 34 D. L. Comins and A. H. Abdullah, J. Org. Chem., 1984, 49,
61, 10827–10852. 3392–3394.
8 R. M. Lanigan, P. Starkov and T. D. Sheppard, J. Org. 35 J. Arguello, L. J. Núnez-Vergara, J. C. Sturm and
Chem., 2013, 78, 4512–4523. J. A. Squella, Electrochim. Acta, 2004, 49, 4849–4856.
9 T. A. Dineen, M. A. Zajac and A. G. Myers, J. Am. Chem. 36 Y. P. Stradyn, Y. I. Beilis, Y. R. Uldrikis, G. Y. Dubur,
Soc., 2006, 128, 16406–16409.
S. E. Sausin and B. S. Chekavichus, Chem. Heterocycl.
Compd., 1975, 11, 1299–1303.
37 E. Booker and U. Eisner, J. Chem. Soc., Perkin Trans. 1,
1975, 929–931.
38 A variety of different reagents for oxidation were
investigated. In detail these attempts can be seen in the
ESI†
10 M. Zhang, S. Imm, S. Bahn, L. Neubert, H. Neumann and
M. Beller, Angew. Chem., Int. Ed., 2012, 51, 3905–3909.
11 C. L. Allen, B. N. Atkinson and J. M. J. Williams, Angew.
Chem., Int. Ed., 2012, 51, 1383–1386.
12 S. N. Rao, D. C. Mohan and S. Adimurthy, Org. Lett., 2013,
15, 1496–1499.
13 M. Tamura, T. Tonomura, K.-I. Shimizu and A. Satsuma, 39 P. E. Dawson, T. W. Muir, I. Clark-Lewis and S. B. H. Kent,
Green Chem., 2012, 14, 717–724. Science, 1994, 266, 776–779.
14 S. Mundinger, U. Jakob and W. Bannwarth, Chem. – Eur. J., 40 P. J. Brignell, U. Eisner and P. G. J. Farrell, Chem. Soc. B,
2014, 20, 1258–1262. 1966, 1083–1089.
15 S. Mundinger, U. Jakob, P. Bichovski and W. Bannwarth, 41 K. Singh and K. Singh, Tetrahedron, 2009, 65, 10395–10399.
J. Org. Chem., 2012, 77, 8968–8979.
42 A. J. Hill and G. E. J. Hall, J. Am. Chem. Soc., 1952, 74, 666–
668.
43 C. L. Allen, A. R. Chhatwal and J. M. J. Williams, Chem.
Commun., 2012, 48, 666–668.
44 S. Y. Lee, C. Lee and D. Y. J. Oh, Org. Chem., 1999, 64,
7017–7022.
45 P. Capdevielle, A. Lavigne and M. Maumy, Tetrahedron,
1990, 46, 2635–2844.
46 P. Borgna, L. Vicarini and C. Calderara, Farmaco, Ed. Sci.,
1977, 32, 813–820.
47 F. Belin, P. Barthélémy, K. Ruiz, J. M. Lacombe and
B. Pucci, Helv. Chim. Acta, 2003, 86, 247–265.
48 P. S. Mahajan, J. P. Mahajan and S. B. Mhaske, Synth.
Commun., 2013, 43, 2508–2516.
49 H.-J. Pi, J.-D. Dong, N. An, W. Du and W.-P. Deng, Tetrahe-
dron, 2009, 65, 7790–7793.
50 S. R. Thopate, S. R. Kote, S. V. Rohokale and N. M. Thorat,
J. Chem. Res., 2011, 35, 124–125.
16 M. C. Bröhmer, S. Mundiger, S. Bräse and W. Bannwarth,
Angew. Chem., Int. Ed., 2011, 50, 6175–6177.
17 R. A. Kramer, M. C. Bröhmer, N. V. Forkel and
W. Bannwarth, Eur. J. Org. Chem., 2009, 4273–4283.
18 M. C. Bröhmer and W. Bannwarth, Eur. J. Org. Chem., 2008,
4412–4415.
19 V. Valerio, D. Petkova, C. Madelaine and N. Maulide, Chem.
– Eur. J., 2013, 19, 2606–2610.
20 Y. Kita, Y. Nishii, Y. Higuchi and K. Mashima, Angew.
Chem., Int. Ed., 2012, 124, 5821–5824.
21 A. Radzicka and R. Wolfenden, J. Am. Chem. Soc., 1996,
118, 6105–6109.
22 R. M. Smith and D. E. Hansen, J. Am. Chem. Soc., 1998,
120, 8910–8913.
23 S. Arseniyadis, A. Wagner and C. Mioskowski, Tetrahedron
Lett., 2004, 45, 2251–2253.
24 W.-R. Li, N.-M. Hsu, H.-H. Chou, S. T. Lin and Y.-S. Lin,
Chem. Commun., 2000, 401–402.
51 C. A. Goodman, J. B. Eagles, L. Rudahindwa,
C. G. Hamaker and S. R. Hitchcock, Synth. Commun., 2013,
43, 2155–2164.
25 T. Kamijo, R. Yamamoto, H. Harada and K. Iizuka, Chem.
Pharm. Bull., 1982, 30, 4242–4244.
26 W. Steglich and G. Höfle, Angew. Chem., Int. Ed. Engl., 1969, 52 R. G. Kalkhambkar, S. N. Waters and K. K. Laali, Tetra-
8, 981. hedron Lett., 2011, 52, 867–871.
27 U. Ragnarsson and L. Grehn, Acc. Chem. Res., 1998, 31, 53 L. Muley, B. Baum, M. Smolinski, M. Freindorf, A. Heine,
494–501.
G. Klebe and D. G. Hangauer, J. Med. Chem., 2010, 53,
2126–2135.
54 M. Bolton and J. Walker, J. Chem. Soc. C, 1967, 2095–2096.
28 J. M. Berg, J. L. Tymoczko and L. Stryer, Biochemistry,
W. H. Freeman and Company, USA, 5th edn, 2003.
29 P. Belenky, K. L. Bogan and C. Brenner, Trends Biochem. 55 E. Reid, J. Am. Chem. Soc., 1917, 39, 124–136.
Sci., 2007, 32, 12–19. 56 I. Dhimitruka and J. SantaLucia, Org. Lett., 2006, 8, 47–50.
30 J.-P. Cheng, Y. Lu, X. Zhu and L. Mu, J. Org. Chem., 1998, 57 R. Hirose, B. G. Kopek, Z.-H. Wang, R. Yusa and
63, 6108–6114. B. W. Baldwin, Tetrahedron, 2003, 9, 1831–1833.
31 A. R. Katritzky, K. Suzuki and Z. Wang, Synlett, 2005, 11, 58 A. Lasslo and W. D. Jordan, J. Org. Chem., 1956, 21, 805–
1656–1665. 805.
32 J. E. Tulor, M. D. Jones, J. M. J. Williams and S. D. Bull, 59 S. A. Rossi, K. W. Shimkin, Q. Xu, L. M. Mori-Quiroz and
J. Org. Chem., 2012, 77, 2808–2818. D. A. Watson, Org. Lett., 2013, 15, 2314–2317.
33 To our knowledge only one example in the literature 60 B. R. Kim, H. Lee, S. Kang, G. H. Sung, J. Kim, J. K. Park,
describes the acylating effect of a 4-substituted 1,4-dihydro-
S. Lee and U. Yoon, Synthesis, 2012, 42–50.
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