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Organic & Biomolecular Chemistry
Page 12 of 13
DOI: 10.1039/C8OB01865K
ARTICLE
Journal Name
918, 740, 642 cm-1; HRMS (ESI TOF) m/z: calcd for IR (ATR): ṽ 3343, 2987, 2936, 2872, 1714, 1661, 1519, 1468,
C19H26N2NaO3S [M + Na]+ 385.1562, found 385.1571.
1392, 1378, 1259, 1220, 1143, 1011, 979, 944, 915, 771, 730
cm-1; HRMS (ESI TOF) m/z: calcd for C28H46N4NaO6S2 [M + Na]+
(RS)-4-Morpholinocarbonyloxy-3-(4-nitrobenzoyl)-2,2,5,5-
tetramethyl-1,3-thiazolidine (2x)
: The carbamate 2x was 621.2756, found 621.2766.
prepared according to the general procedure using 2,2,5,5-
tetramethyl-2,5-dihydro-1,3-thiazole (286 mg, 2.00 mmol), 4-
nitrobenzoyl chloride (445 mg, 2.40 mmol), triethylamine (506
mg, 5.00 mmol) and morpholine (261 mg, 3.00 mmol). The
crude product was purified by column chromatography (n-
hexane/EtOAc 2:1, Rf = 0.42) to obtain 616 mg (1.45 mmol) of
a colorless solid (yield: 73%).
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
MP: 180–181 °C (EtOAc/n-hexane); 1H NMR (500.1 MHz, CDCl3,
299.4 K): δ 1.24 (s, 3 H), 1.65 (s, 3 H), 1.96 (s, 3 H), 2.06 (s, 3 H),
3.25–3.37 (m, 2 H), 3.44–3.55 (m, 2 H), 3.60–3.68 (m, 4 H),
6.10 (s, 1 H), 7.48–7.52 (m, 2 H), 8.24–8.28 (m, 2 H) ppm; 13C
NMR (125.8 MHz, CDCl3, 299.4 K): δ 23.1, 30.9, 31.0, 31.6,
44.0, 44.6, 53.2, 66.6, 66.7, 73.2, 94.4, 124.1, 127.3, 143.3,
148.5, 153.1, 168.8 ppm; IR (ATR): ṽ 2988, 2932, 2858, 1703,
1660, 1520, 1371, 1341, 1219, 1114, 1077, 979, 860, 836, 766
cm-1; HRMS (ESI TOF) m/z: calcd for C19H25N3NaO6S [M + Na]+
446.1362, found 446.1354.
We are thankful to the Central analytic section of the
University of Oldenburg for retrieving NMR and MS data.
Notes and references
1
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,
6201; (b) D. Yu, S. P. Teong and Y. Zhang, Coord. Chem. Rev.,
2015, 293–294, 279.
(RS)-3-Acetyl-4-(4-pyrimidin-2-ylpiperazin-1-yl)carbonyloxy-
2,2,5,5-tetramethyl-1,3-thiazolidine (2y): The carbamate 2y
was prepared according to the general procedure using
2,2,5,5-tetramethyl-2,5-dihydro-1,3-thiazole (286 mg, 2.00
mmol), acetyl chloride (188 mg, 2.40 mmol), triethylamine
(1.113 g, 11.00 mmol) and 1-(2-pyrimidyl)piperazine
dihydrochloride (711 mg, 3.00 mmol). The crude product was
purified by column chromatography (n-hexane/EtOAc 3:7, Rf =
0.35) to obtain 372 mg (0.95 mmol) of a colorless oil (yield:
47%).
1H NMR (500.1 MHz, CDCl3, 300.2 K): δ 1.32 (s, 3 H), 1.59 (s, 3
H), 1.83 (s, 3 H), 1.95 (s, 3 H), 2.23 (s, 3 H), 3.49–3.68 (m, 4 H),
3.73–3.96 (m, 4 H), 6.42 (s, 1 H), 6.53 (t, J = 4.7 Hz, 1 H), 8.32
(d, J = 4.7 Hz, 2 H) ppm; 13C NMR (125.8 MHz, CDCl3, 299.2 K):
δ 23.3, 25.4, 30.7, 30.8, 32.0, 43.66, 43.66, 43.71, 44.1, 52.7,
73.3, 94.3, 110.7, 154.3, 157.9, 161.7, 170.3 ppm; IR (ATR): ṽ
2991, 2935, 2858, 1698, 1676, 1584, 1495, 1427, 1377, 1212,
1071, 798 cm-1; HRMS (EI 70 eV) m/z: calcd for C18H27N5O3S
[M]+ 393.1829, found 393.1834.
3
4
D. J. Darensbourg, Chem. Rev., 2007, 107, 2388.
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A. Olah and S. R. Narayanan, J. Am. Chem. Soc., 2011, 133
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X. Guo, C.-L. Zhong, L.-N. He, Y.-N. Zhao, Q.-W. Song, A.-H.
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(R*,S*)-
and
(R*,R*)-Adipoylbis(2,2,5,5-
tetramethylthiazolidine-3,4-diyl) bis(allylcarbamate) (2z): The
carbamate 2z was prepared according to the general
procedure using 2,2,5,5-tetramethyl-2,5-dihydro-1,3-thiazole
(286 mg, 2.00 mmol), adipoyl chloride (183 mg, 1.00 mmol),
triethylamine (506 mg, 5.00 mmol) and allylamine (171 mg,
3.00 mmol). The crude product was purified by column
chromatography (n-hexane/EtOAc 7:3, Rf = 0.17) to obtain 336
mg (0.56 mmol) of a colorless oil (yield: 56%).
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6
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7
8
,
1H NMR (500.5 MHz, CDCl3, 300.0 K): δ 1.33 (s, 6 H), 1.56 (s, 6
H), 1.61–1.69 (m, 4 H), 1.80 (s, 6 H), 1.92 (s, 6 H), 2.33–2.41 (m,
2 H), 2.46–2.55 (m, 2 H), 3.73–3.89 (m, 4 H), 4.96–5.03 (m, 2
H), 5.12–5.22 (m, 4 H), 5.78–5.88 (m, 2 H), 6.39 (s, 2 H) ppm;
13C NMR (125.9 MHz, CDCl3, 300.0 K): δ 23.07, 23.07 24.6,
24.7, 30.75, 30.75, 30.76, 30.76, 32.11, 32.11, 36.1, 36.2,
43.54, 43.54, 52.74, 52.74, 73.39, 73.39, 92.59, 92.61, 116.62,
116.62, 134.07, 134.07, 155.26, 155.26, 172.42, 172.42 ppm;
9
D. Luo, L. Liu, P. Han, Q. Wei and H. Shen, Int. Urogynecol. J.,
2012, 23, 983.
10 H.-Z. Bu, W. F. Pool, E. Y. Wu, S. R. Raber, M. A. Amantea and
B. V. Shetty, Drug Metab. Dispos., 2004, 32, 689.
11 R. L. Baron and T. L. Merriam, In Reviews of Environmental
Contamination and Toxicology: Toxicology of Aldicarb; G. W.
Ware, Eds.; Springer: New York, 1988, 105, 1.
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2010, 12, 1340; (b) D. Chaturvedi, Tetrahedron, 2012, 68, 15.
12 | J. Name., 2012, 00, 1-3
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