RSC Advances
-[4,5-Dihydroxy-6-(5-hydroxy-4-iodo-3-methyl-pyrazol-1-yl)-2-
hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-
tetrahydro-pyran-3,4,5-triol (9b)
Paper
2
Acknowledgements
This work is nancially supported by GEMTEX Laboratory
France. We thank Mr Christian Catel (technician of GEMTEX
laboratory) for its kind disponibility.
The product 9b was prepared according to the general proce-
dure in 88% as yield. 9b is obtained as a colored solid as a
1
mixture of a and b pyranosic anomers. H NMR (200 MHz,
Me
2
SO): d ¼ 11.58 (s, 1H, OH), 5.11–4.57 (m, 2H, both anomers),
4
.31–4.13 (m, 4H, both anomers), 3.88–3.78 (m, 6H, both Notes and references
anomers), 3.44–3.41 (m, 2H, both anomers), 2.73 (s, 3H, CH ,
3
1
3
1 K. Hunger, Industrial Dyes: Chemistry, Properties,
Applications, Wiley-VCH, Weinheim, Germany, 2003.
2 A. Bafana, S. S. Devi and T. Chakrabarti, Environ. Rev., 2011,
Pyr) ppm. C NMR (50 MHz, Me SO): see Table 6 in the ESI† for
2
the glycidic part and d ¼ 155.7, 138.3, 60.2, 12.6 ppm. MS (ESI):
+
m/z ¼ 549.28 [M + 1] . C16
2
H25IN O11 (548.05): calcd, 35.05; H,
19, 350.
4.60; N, 5.11 found: 35.23; H, 4.77; N, 5.24.
3
4
R. Bianchini, G. Catelani, E. Frino, J. Isaad and M. Rolla,
BioResources, 2007, 2, 630.
R. Bianchini, G. Catelani, R. Cecconi, F. D'Andrea,
L. Guazzelli, J. Isaad and M. Rolla, Eur. J. Org. Chem., 2008,
5-Hydroxy-4-iodo-1-(3,4,5-trihydroxy-6-hydroxymethyl-
tetrahydro-pyran-2-yl)-1H-pyrazole-3-carboxylic acid ethyl
ester (9c)
3
, 444.
The product 9c was prepared according to the general proce-
dure in 89% as yield. 9c is obtained as a colored solid as a
mixture of a and b pyranosic anomers. H NMR (200 MHz,
5 R. Bianchini, G. Catelani, R. Cecconi, F. D'Andrea, E. Frino,
J. Isaad and M. Rolla, Carbohydr. Res., 2008, 343, 2067.
6 J. Isaad, M. Rolla and R. Bianchini, Eur. J. Org. Chem., 2009,
2748.
7 J. Isaad, F. Malek and A. El Achari, Dyes Pigm., 2012, 92, 1212.
8 R. Bianchini, M. Rolla, J. Isaad, G. Catelani, L. Guazzelli,
M. Corsi and M. Bonanni, Carbohydr. Res., 2012, 356, 104.
9 J. Isaad and A. Perwuelz, Tetrahedron Lett., 2010, 51, 5328.
1
Me SO): d ¼ 11.55 (s, 1H, OH), 5.28–5.21 (d, 1H), 4.25 (q, 2H,
2
CH
2
), 3.82–3.60 (m, 4H), 3.48–3.31 (m, 2H), 1.33 (t, 3H, CH
3
)
1
3
ppm. C NMR (50 MHz, Me
2
SO): see Table 5 in the ESI† for the
glycidic part and d ¼ 159.6, 151.2, 62.1, 58.3, 13.7 ppm. MS (ESI):
+
m/z ¼ 445.23 [M + 1] . C12
2 8
H17IN O (444.03): calcd C, 27.85; H,
3
.38; N, 7.22; C, 32.45; H, 3.86; N, 6.31 found: C, 32.57; H, 3.98; 10 V. Pasquet, N. Behary, A. Perwuelz and J. Isaad, Fibers Polym.,
N, 6.45.
2013, 14, 1141.
1
1
1
1
1
1
1
1
1 J. Isaad, Tetrahedron, 2013, 69, 2239.
2 J. Isaad and F. salaun, Sens. Actuators, B, 2011, 157, 26.
3 J. Isaad and A. El achari, Anal. Chim. Acta, 2011, 694, 120.
4 J. Isaad and A. El Achari, Tetrahedron, 2011, 67, 4196.
5 J. Isaad and A. El Achari, Tetrahedron, 2011, 67, 4939.
6 J. Isaad and A. El achari, Tetrahedron, 2011, 67, 5678.
7 J. Isaad and A. Perwuelz, Tetrahedron Lett., 2010, 51, 5810.
8 J. Dakin and B. Culshaw, Optical Fiber Sensors, Artech House,
Boston-London, 1997, vol. IV, ch. 8, pp. 53–107.
9 Z. Czech, A. Butwin, E. Herko, B. Hefczyc and J. Zawadiak,
eXPRESS Polym. Lett., 2008, 12, 277.
1
-[3,4-Dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-
hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-
yl]-5-hydroxy-4-iodo-1H-pyrazole-3-carboxylic acid ethyl ester
(
9d)
The product 9d was prepared according to the general proce-
dure in 88% as yield. 9d is obtained as a colored solid as a
mixture of a and b pyranosic anomers. H NMR (200 MHz,
1
Me
.31–4.12 (m, 6H, both anomers), 3.88–3.78 (m, 6H, both
anomers), 3.46–3.41 (m, 2H, both anomers), 1.32 (t, 3H, CH
2
SO): d ¼ 11.56 (s, 1H, OH), 5.12–4.56 (m, 2H, both anomers),
1
2
2
2
2
4
3
)
0 X. Tong, G. Wang and Y. Zhao, J. Am. Chem. Soc., 2006, 128,
1
3
ppm. C NMR (50 MHz, Me SO): see Table 6 in the ESI† for the
2
8746.
glycidic part and d ¼ 155.7, 138.3, 60.2, 12.9 ppm. MS (ESI): m/z
1 H. Durr and H. Bouas-Laurent, Photochromism: Molecules
and Systems, Elsevier, Amsterdam, 2003.
2 A. Zarei, A. R. Hajipour, L. Khazdooz, B. F. Mirjalili and
R. A. Naja, Dyes Pigm., 2009, 81, 240.
+
¼
549.28 [M + 1] . C H IN O (548.05): calcd, 35.05; H, 4.60;
1
6
25
2 11
N, 5.11 found: 35.23; H, 4.77; N, 5.24.
3 A. Morsy and M. El-Apasery, J. Appl. Polym. Sci., 2008, 109,
Conclusions
695.
In summary, we have developed an efficient and experimentally 24 N. Noroozi-Pesyan, J. Khalafy and Z. Malekpoor, Progress in
simple method for the diazotization–iodination of aromatic Color Colorants and Coatings, 2009, 1, 61.
amines in the presence of N-propyl-2-pyrrolidonium hydrogen 25 N. Noroozi-Pesyan, J. Khalafy and Z. Malekpoor, J. Chin.
sulfate ([H-NPP]HSO ) supported on nano-sized silica-coated Chem. Soc., 2009, 56, 1018.
magnetite as acid catalyst under solvent-free conditions in 26 Y. Moglie, C. Vitale and G. Radivoy, Tetrahedron Lett., 2008,
good to excellent yields. The sequential diazotization–iodin- 49, 1828–1831.
ation take place in the presence of the acidic Fe O @SILnP as a 27 F. Ahmed Khan, J. Dash, C. Sudheer and R. K. Gupta,
4
3
4
mild and new proton source and the resulting diazonium salts
are stable and react rapidly with potassium iodide to produce 28 B. J. P. Whalley, H. G. V. Evans and C. A. Winkler, Can. J.
aryl iodides. Chem., 1956, 34, 1154.
Tetrahedron Lett., 2003, 44, 7783.
49340 | RSC Adv., 2014, 4, 49333–49341
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