3
3
.
(a) Gyenis, L.; Kuś, A.; Bretner, M.; Litchfield, D. W. J.
prepare diverse substituted ninhydrins in a single step with very
good yields.
Proteomics. 2013, 81, 70-79. (b) Unger, G. M.; Davis, A. T.;
8
Anticancer Drugs 2005, 16, 1037-1043. (d) Landesman-Bollag,
E.; Romieu-Mourez, R.; Song, D. H.; Sonenshein, G. E.; Cardiff,
R. D.; Seldin, D. C. Oncogene 2001, 20, 3247-3257. (e) Yenice,
S.; Davis, A. T.; Goueli, S. A.; Akdas, A.; Limas, C.; Ahmed, K.
Prostate 1994, 24, 11-16. (f) Daya-Makin, M.; Sanghera, J. S.;
Mogentale, T.; Lipp, M.; Parchomchuk, J.; Hogg J.; Pelech, S. L.
Cancer Res. 1994, 54, 2262-2268. (g) Stalter, G.; Siemer, S.,
Becht, E.; Ziegler, M.; Remberger, K.; Issinger, O. G. Biochem.
Biophys. Res. Commun. 1994, 202, 141-147.
Table 2 Oxidation of Several Indan-1-ones
4
.
(a) Cozza, G.; Pinna L. A.; Moro S. Curr. Med. Chem. 2013, 20,
6
71-693. (b). Cozza, G., Bortolato, A.; Menta, E.; Cavalletti, E.;
Spinelli, S.; Moro, S. Anticancer Agents Med. Chem. 2009, 9, 778-
86.
Yield
(%)
lit.
N°
ref.
lit.
13
7
Ninhydrin
2
Yield
(%)
R1
R2
R3
R4
5. Trembley, J. H.; Unger, G. M.; Korman, V. L.; Tobolt, D. K.;
Kazimierczuk. Z.; Pinna, L. A.; Kren, B. T.; Ahmed, K. Cancer
lett. 2012, 315, 48-58.
a
H
H
H
H
H
H
H
84
79
85
2
2
a
6
.
Hundsdörfer, C.; Hemmerling, H-J.; Götz, C.; Totzke, F.;
a
Me
21
10c
Bednarski, P.; Le Borgne, M.; Jose, J. Bioorg. Med. Chem. 2012,
b
2
0, 2282-2289.
c
9d,
9e
7. (a) Hemmerling, H. J.; Reiss, G. Synthesis 2009, 6, 985-999. (b)
H
F
H
H
H
H
Br
H
70
81
#
2
c
Hemmerling, H. J.; Reiss, G.; Götz, C.; Jose, J. WO 2008040547,
2
008. (c) Hemmerling, H. J.; Merschenz-Quack, A.; Wunderlich,
c
10d,
10e
#
H. Z. Naturforsch., B: Chem. Sci. 2004, 59, 1143-1152.
2
d
8
9
.
.
Ruhemann, S. Trans. Chem. Soc. 1910, 97, 1438-1449.
(a) Hark, R. R.; Hauze, D. B.; Petrovskaia, O.; Hansen, D. B.;
Joullié, M. M. Chem. Soc. Rev. 2005, 34, 408-417. (b) Joullié, M.
Can. J. Chem. 2001, 79, 1632-1654. (c) Joullié, M. M.;
Thompson, R. R.; Nemeroff, N. H. Tetrahedron 1991, 47, 8791-
H
H
H
H
H
H
H
H
H
H
H
H
H
H
Br
H
CF
3
66
74
74
87
87
80
86
nd
10a
10b
9d
2
e
a*
NO
2
100
2
f
c
8
830. (d) Lennard, C. J.; Margot, P. A.; Stoilovic, M.; Warrener,
H
OH
OMe
H
#
2
2
g
R. N. J. For. Sci. Soc. 1986, 26, 323-328. (e) Lennard, C. J.;
Margot, P. A.; Stoilovic, M.; Warrener, R. N. J. For. Sci. Soc.
b
H
58
h
1
988, 28, 3-23.
a
Me
H
61
10c
10c
10c
10. (a) Jung, Y. S.; Lee, C. K.; Choi, I. Y.; Kim, H. S.; Kim, P. H.;
Han, S. B.; Neyts, J.; Thibaut, H. J. Eur. Pat. 2,722,322, 2014. (b)
Jung, Y. S.; Lee, C. K.; Kim, H. S.; Jeong, H. C.; Kim, P. H.; Han,
S. B.; Shin, J. S.; Neyts, J.; Thibaut, H. J. Eur. Pat. 2,722,042,
2
i
a
H
45
2
j
a
F
H
40
2
2
014. (c) Zhang, Z. ; Du, X.; Chopiuk, G. PCT Int. WO 02/02562,
002. (d) Desquand, S.; Finet, M.; Le Maquer, F.; Tembo, N. O.;
2
k
c
9d,
9e
H
NO
2
H
H
70
#
Torregrosa, J.-L.; Yannic-Arnoult, S. Eur. Pat. 0,646,579, 1995.
e) Desquand, S.; Finet, M.; Le Maquer, F.; Tembo, N. O.;
Torregrosa, J.-L.; Yannic-Arnoult, S. Eur. Pat. 0,646,574, 1995.
f) Cugnon de Sevricourt, M.; Dacquet, C.; Finet, M.; Le Marquer,
2
l
(
b
H
H
H
H
H
OH
OMe
H
H
H
73
85
67
80
27
10f
16a
nd
2
m
(
a
F.; Robba, M.; Tembo, N. O.; Yannic-Arnoult, S.; Torregrosa, J.-
L. Eur. Pat. 0,566,446, 1993.
73
2
n
o
p
OMe
H
OMe
H
11. (a) Sharma, A. K.; Subramani, A. V.; Gorman C. B. Tetrahedron
2
2
007, 63, 389-395. (b) Levy, J.-N.; Latham, C. M.; Roisin, L.;
a
OMe OMe
53
14c
Kandziora, N.; Di Fruscia, P.; White, A. J. P.; Woodward, S.;
Fuchter, M. J. Org. and Biomol. Chem. 2012, 10, 512-515. (c)
Kamiya, N.; Tomonaga, A.; Sugiyama, H. Eur. Pat. 2,647,622,
2013. (d) Chow, K.; Fang W. K.; Corpuz, E.; Gil D. W. ; Garst,
M. E. US. Pat. 0,255,230, 2008. (e) Nguyen, P.; Corpuz, E.;
Heidelbaugh, T. M.; Chow, K.; Garst, M. E. J. Org. Chem. 2003,
68, 10195-10198.
2
a
:
yield described from the corresponding indanone; the oxidation method
b
could be different; : yield not described from the corresponding indanone;
c
yield described from the corresponding indane-1,3-dione; : yied not
*
specified; : described without any purification; nd : not described
1
1
1
2. Rubin, M. B.; Gleiter, R. Chem. Rev. 2000, 100, 1121-1164.
3. Bowden, K., Rumpal, S. J. Chem. Res. Miniprint 1997, 355-363.
4. (a) Tatsugi, J.; Izawa, Y. Synthetic Comm. 1998, 28, 859-864. (b)
Heffner, R. J.; Joullié, M. M. Synth. Comm. 1991, 21, 2231-2256.
Acknowledgments
(
c) Maslak, P.; Chopra, A.; Moylan, C. R.; Wortmann, R.; Lebus,
S.; Rheingold, A. L.; Yap, G. P. A. J. Am. Chem. Soc. 1996, 118,
471-1481.
The authors are grateful to Rhône-Alpes region for the
microwave acquisition. M. Abdelhamid Nacereddine thanks the
Algerian Ministry of Foreign Affairs and the Institut Français
d’Algérie for his doctoral fellowship.
1
1
1
5. (a) Smith, M. B. Organic Synthesis Int. Ed.; McGraw-Hill Int.
Ed.: Singapore, 1994, 311. (b) Sharpless, K. B.; Gordon, K. M. J.
Am. Chem. Soc. 1976, 98, 300-301.
6. (a) Reniers, J.; Meinguet, C.; Moineaux, L.; Masereel, B.;
Vincent, S.P.; Frédérick, R.; Wouters, J. Eur. J. Med. Chem. 2011,
Supplementary data
4
6, 6104-11. (b) Frédérick, R.; Dumont, W.; Ooms, F.;
Aschenbach, L.; Van der Schyf, C. J.; Castagnoli, N.; Wouters, J.;
Krief, A. J. Med. Chem. 2006, 49, 3743-3747.
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.tetlet.
(a) Loupy, A. Microwaves in Organic Synthesis 2d ed.; Wiley-
VCH: Weinheim, 2006. (b) Di Fabio, G.; Romanucci, V.; De
Nisco, M.; Pedatella, S.; Di Marino, C.; Zarrelli, A. Tetrahedron
Lett. 2013, 54, 6279-6282. (c) Bagley, M. C.; Lin, Z.; Pope, S. J.-
A. Tetrahedron Lett. 2009, 50, 6818-6822. (d) Hosseini, A.;
Halvagar, M. R.; Khalilzadeh, M. A.; Alaee, E.; Tajbakhsh, M. J.
Chem. Res. 2005, 1, 48-49.
References and notes
1
2
.
.
Sarno, S.; Ghisellini, P.; Pinna, L.A. J. Biol. Chem. 2002, 277,
2509-22514.
Guerra, B.; Issinger, O.-G. Curr. Med. Chem. 2008, 15, 1870-
886.
2
1