F
M. Stefaniak, J. Romański
Paper
Synthesis
HRMS-ESI: m/z [M + Na]+ calcd for C18H36O8S2Na: 467.1749; found:
467.1741.
Estimated yield = 24% (ca. 100 mg) not fully characterized (see main
text).
1H NMR (600 MHz, CDCl3): δ = 3.94–3.98 (m), 3.79–3.63 (m), 2.99–
2.90 (m), 2.81–2.46 (m), 2.02–1.91 (m), 1.59–1.56 (m).
Compound 7e
13C NMR (151 MHz, CDCl3): δ = 95.4, 95.3, 95.0, 94.9, 72.9, 71.2, 71.2,
71.0, 70.5, 70.4, 70.3, 70.2, 69.7, 69.6, 68.7, 68.5, 68.3, 59.8, 59.1, 58.7,
57.9, 49.1, 48.2, 47.7, 47.2, 44.1, 43.9, 43.8, 43.4, 41.5, 41.3, 41.2, 40.9,
40.8, 40.3, 39.2, 38.4, 37.9, 37.8, 32.2, 31.7, 31.5, 31.4.
Prepared in the presence of K2CO3.
Yield: 47.5% (190 mg).
IR (film): 2918, 2870, 1354, 1294, 1111, 1040 cm–1
1H NMR (600 MHz, CDCl3): δ = 3.97–3.96 (m, 1 H), 3.71–3.58 (m,
.
10 H), 3.54–3.50 (m, 1 H), 2.83–2.68 (m, 4 H).
13C NMR (151 MHz, CDCl3): δ = 32.1, 32.2, 35.9, 70.2, 70.3, 70.5, 70.6,
71.2, 71.3, 74.3, 74.4, 74.3, 71.3, 71.2, 70.6, 70.5, 70.3, 70.2, 35.9, 32.2,
32.1.
HRMS-ESI: m/z [M + Na]+ calcd for C16H32O7S2Na: 423.1487; found:
423.1475.
Funding Information
Authors acknowledge financial support from National Science Center
in Cracow (Poland) (Preludium 9 Grant No. UMO-2015/17/N/ST5/03028).
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Compound 7f
References
Prepared in the presence of Cs2CO3.
(1) Meadow, J. R.; Reid, E. E. J. Am. Chem. Soc. 1934, 56, 2177.
(2) (a) Izatt, R. M.; Terry, R. E.; Hansen, L. D.; Avondet, A. G.;
Bradshaw, J. S.; Dalley, N. K.; Jensen, T. E.; Christensen, J. J. Inorg.
Chim. Acta 1978, 30, 1. (b) Tsuchiya, T.; Shimizu, T.; Kamigata, N.
J. Am. Chem. Soc. 2001, 123, 11534. (c) Kim, S.; Lindoy, L. F.; Lee,
S. S. Coord. Chem. Rev. 2014, 280, 176. (d) Cicek, B.; Calisir, U.
Lett. Org. Chem. 2016, 13, 572.
Yield: 45% (220 mg).
IR (film): 2914, 2866, 1350, 1116, 1036 cm–1
1H NMR (600 MHz, CDCl3): δ = 3.95–3.92 (m, 1 H), 3.71 (t, J = 6.6 Hz,
2 H), 3.68–3.59 (m, 12 H), 3.54–3.51 (m, 1 H), 2.78 (t, J = 6.6 Hz, 2 H),
2.72 (t, J = 6.0 Hz, 2 H).
.
13C NMR (151 MHz, CDCl3): δ = 74.2, 74.2, 71.2, 70.6, 70.4, 70.3, 70.2,
(3) (a) Baumann, T. F.; Reynolds, J. G.; Fox, G. A. React. Funct. Polym.
2000, 44, 111. (b) Fedorova, O. A.; Fedorov, Y. V.; Vedernikov, A.
I.; Gromov, S. P.; Yescheulova, O. V.; Alfimov, M. V.; Woerner,
M.; Bossmann, S.; Braun, A.; Saltiel, J. J. Phys. Chem. A 2002, 106,
6213. (c) Lee, T. K.-M.; Zhu, N.; Yam, V. W.-W. J. Am. Chem. Soc.
2010, 132, 17646. (d) Ingram, J. D.; Costa, P. J.; Adams, H.; Ward,
M. D.; Félix, V.; Thomas, J. A. Inorg. Chem. 2012, 51, 10483.
(4) Litvinova, V. V.; Anisimov, A. V. Chem. Heterocycl. Compd. 1999,
35, 1385.
69.8, 35.6, 31.9.
HRMS-ESI: m/z [M + Na]+ calcd for C20H40O9S2Na: 511.2011; found:
511.1996.
Compound 7g
Prepared in the presence of K2CO3.
Yield: 45% (195 mg).
IR (film): 2920, 2863, 1261, 1103, 1036 cm–1
1H NMR (600 MHz, CDCl3): δ = 3.91–3.88 (m, 1 H), 3.71–3.66 (m, 7 H),
2.86–2.79 (m, 6 H), 2.74–2.71 (m, 2 H).
13C NMR (151 MHz, CDCl3): δ = 71.2, 70.7, 70.3, 70.0, 38.8, 38.7, 32.4,
32.3.
HRMS-ESI: m/z [M + Na]+ calcd for C18H36O8S2Na: 467.1749; found:
467.1740.
.
(5) Siswanta, D.; Nagatsuka, K.; Yamada, K.; Kumakura, K.;
Hisamoto, H.; Shichi, Y.; Toshima, K.; Suzuki, K. Anal. Chem.
1996, 68, 4166.
(6) (a) Ikeda, I.; Tsuji, Y.; Nakatsuji, Y.; Okahara, M. J. Org. Chem.
1986, 51, 1128. (b) Pett, V. B.; Legett, G. H.; Cooper, T. H.; Reed,
P. R.; Situmeang, D.; Ochrymowycz, L. A.; Rorabacher, D. B.
Inorg. Chem. 1988, 27, 2164. (c) Bradshaw, J. S. J. Inclusion
Phenom. Mol. Recognit. Chem. 1997, 29, 221. (d) Zoghlami, H.;
Romdhani-Younes, M.; Chaabouni, M. M.; Baklouti, A. Tetrahe-
dron Lett. 2011, 52, 881. (e) Shimizu, T.; Kuwahara, J.;
Komatsuzaki, S.; Hirabayashi, K. Supramol. Chem. 2011, 23, 88.
(7) (a) Fu, X.; Wu, S. Synth. Commun. 1997, 27, 1677. (b) Azoulay, S.;
Manabe, K.; Kobayashi, S. Org. Lett. 2005, 7, 4593. (c) Robin, A.;
Brown, F.; Bahamontes-Rosa, N.; Wu, B.; Beitz, E.; Kun, J. F. J.;
Flitsch, S. L. J. Med. Chem. 2007, 50, 4243.
(8) (a) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Green Chem.
2003, 5, 436. (b) De, S.; Khan, A. Chem. Commun. 2012, 3130.
(9) Arya, A.; Kumar, V.; Mathur, D.; Singh, S.; Brahma, R.; Singh, R.
J. Heterocycl. Chem. 2015, 52, 1.
(10) Fan, Y.; Shang, X.; Liu, Z.; Wu, L. Synth. Commun. 2006, 36, 3149.
(11) (a) Amantini, D.; Fringuelli, F.; Piermatti, O.; Tortoioli, S.;
Vaccaro, L. ARKIVOC 2002, (xi), 293. (b) Azizi, N.; Batebi, E. Catal.
Sci. Technol. 2012, 2, 2445.
Compound 8a
Prepared in the presence of Na2CO3.
Yield: 47% (160 mg).
IR (film): 2923, 2865, 1475, 1346, 1262, 938, 872 cm–1
.
1H NMR (600 MHz, CDCl3): δ = 3.97–3.83, (m, 2 H), 3.07–2.90, (m,
4 H), 2.80–2.52 (m, 10 H), 2.50–2.37 (m, 2 H), 2.08–1.98 (m, 5 H),
1.55–1.50 (m, 1 H).
13C NMR (151 MHz, CDCl3): δ = 94.7, 94.6; 94.6, 71.6, 71.5, 68.5, 68.2,
67.7, 67.4, 60.8, 60.1, 58.2, 56.8, 50.3, 49.6, 47.5, 46.3, 44.2, 44.0, 43.9,
43.7, 43.6, 43.5, 41.7, 41.7, 41.6, 41.6, 41.5, 41.4, 41.2, 41.0, 37.9, 37.7,
31.4, 31.3.
ESI-MS: m/z = 411 [M·++1], 433 [M·++Na].
(12) (a) Cookson, R. C.; Grundwell, E.; Hudec, J. Chem. Ind. 1958,
1003. (b) Marchand, A. P.; Allen, R. W. J. Org. Chem. 1974, 39,
1596.
Compound 8b
Prepared in the presence of K2CO3.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2019, 51, A–G