Unusual direction of cyclocondensation of 1-(4-chlorophenyl)-3,5-diamino-1, 2,4-triazole, pyruvic acid, and aldehydes

Article abstract of DOI:10.1055/s-0030-1258468

The reactivity of 1-(4-chlorophenyl)-3,5-diamino-1,2,4-triazole in multicomponent reactions with pyruvic acid and aldehydes and in two-component reactions with arylidenepyruvic acid was studied. The unusual direction of these treatments leading to the formation of unprecedented 3-[5-amino-1-(4- chlorophenyl)-1,2,4-triazol-3-ylamino]-5-arylfuran-2-ones instead of triazolopyrimidine or triazolylpyrrolone derivatives was found and discussed. Georg Thieme Verlag Stuttgart.

Full text of DOI:10.1055/s-0030-1258468

1120
PAPER
Unusual Direction of Cyclocondensation of 1-(4-Chlorophenyl)-3,5-diamino-
1,2,4-triazole, Pyruvic Acid, and Aldehydes
Yana I. Sakhno,a Sergey M. Desenko,a,b Svetlana V. Shishkina,a Oleg V. Shishkin,a,b Vladimir I. Musatov,a
Valentyn A. Chebanov*a
a
SSI ‘Institute for Single Crystals’ NAS of Ukraine, Lenin Ave. 60, Kharkiv 61001, Ukraine
Fax +38(57)3410273; E-mail: chebanov@isc.kharkov.com
V. N. Karazin Kharkiv National University, Svobody sq. 4, Kharkiv 61077, Ukraine
b
Received 25 November 2010; revised 4 February 2011
Scheme 1) as it was observed for other types of (di)amino-
Abstract: The reactivity of 1-(4-chlorophenyl)-3,5-diamino-1,2,4-
1,2,4-triazoles.1 On the hand, in some cases the isolation
triazole in multicomponent reactions with pyruvic acid and alde-
of only noncyclized compounds like 4, 5 and similar prod-
hydes and in two-component reactions with arylidenepyruvic acid
was studied. The unusual direction of these treatments leading to the
ucts was described.6 Another possible direction of hetero-
formation of unprecedented 3-[5-amino-1-(4-chlorophenyl)-1,2,4- cyclization leading to pyrrolone derivatives 9 was
triazol-3-ylamino]-5-arylfuran-2-ones instead of triazolopyrimi-
observed in the multicomponent reaction between phe-
dine or triazolylpyrrolone derivatives was found and discussed.
nylpyruvic acid (7), 1-(4-chlorophenyl)-3,5-diamino-
1,2,4-triazole (6), and aromatic aldehydes 8a–f.2c
Key words: heterocycles, multicomponent reaction, furans, nu-
cleophiles, regioselectivity
R1
N
N
R1
O
Alk
Pyruvic acid and its derivatives play an important role in
biological processes and being a part of some pharmaco-
logically active compounds are challenging building
blocks for heterocyclization reactions.1 In our recent pub-
lications, several examples of multicomponent and se-
quential (linear) reactions involving pyruvic acids and
polyfuctional aminoazoles were discussed from the view-
points of their selectivity and molecular diversity.2 In par-
ticular, the influence of temperature, catalytic system,
activation method, and structural factors on the reaction
directions were presented. It was shown that variation of
these parameters can be effective tools to control the se-
lectivity of processes involving pyruvic acids2 as well as
other types of heterocyclizations.3
H2N
N
N
O
O
N
N
+
R3
H2N
NH2
R3
R2
N
O
R2
1
2
3
R1
R1
N
N
N
N
O
NH
NH2
O
N
N
N
N
H
H
O
5
O
O
O
4
Cl
R
8a–f
Cl
H
O
O
OH
N
N
Among the polyfunctional aminoazoles applied in hetero-
cyclizations with carbonyl compounds, 3,5-diamino-
1,2,4-triazole is an attractive target due to the presence of
several alternative reaction centers and possibility of fur-
ther modification of the cyclization products. The usual
direction of multicomponent reactions of this diamino-
azole with aldehydes and active methylene compounds
(CH acids) is a formation of pyrimidine ring with partici-
pation of NH2 group and one of the endocyclic nitrogen.1,4
The second amino group is able to take part in further
transformations of the heterocycles obtained.4b Introduc-
ing an aryl substituent at position 1 of the diaminotriazole
gave rise to specific properties, which have been studied
in detail by Chernyshev et al.,5 Papini et al.,6 and other au-
thors.7,8 However, the reactions of 1-aryl-substituted 3,5-
diamino-1,2,4-triazoles 1 with b-keto esters 2 led to the
formation of pyrimidine cycles5a,8 (compounds 3,
O
+
NH2
N
N
O
N
N
Ph
HO
NH2
7
H2N
N
R
Ph
6
9
Scheme 1
Thus, 1-aryl-substituted (di)amino-1,2,4-triazoles are able
to participate in reactions with electrophiles with forma-
tion of several types of heterocyclic or noncyclic final
compounds. In the present article, we describe a new un-
usual direction of the multicomponent treatment9 of 1-(4-
chlorophenyl)-3,5-diamino-1,2,4-triazole with pyruvic
acid and aldehydes or its linear reactions with
arylidenepyruvic acids yielding earlier undisclosed deriv-
atives of triazolylfuranone.
It was established that three-component treatment of 1-(4-
chlorophenyl)-3,5-diamino-1,2,4-triazole (6), aromatic
aldehydes 8a–f, and pyruvic acid (10) in boiling DMF
took place in an unusual direction and unexpectedly gave
SYNTHESIS 2011, No. 7, pp 1120–1124
Advanced online publication: 08.03.2011
DOI: 10.1055/s-0030-1258468; Art ID: T22610SS
© Georg Thieme Verlag Stuttgart · New York
x
x
.
x
x
.2
0
1
1

PAPER
Unusual Multicomponent Reaction of Aminotriazole with Pyruvic Acid and Aldehydes
1121
Cl
R
O
O
N
N
R
+
N
H
11a–f
H2N
Cl
N
8a–f
H
O
DMF, Δ
Cl
O
(method A)
OH
N
N
– 2 H2O
H2N
NH2
N
R
O
10
6
N
N
N
H2N
//
OH
N
O
12
O
EtOH–H2O
OH–
OH
O
6, DMF, Δ
(method B)
11a–f
8
+ 10
– H2O
– H2O
R
13a–f
Scheme 2
as the sole reaction product unprecedented 3-[5-amino- vic acid, formation of azomethine 14, and further cycliza-
1-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamino]-5-arylfu- tion of its enamine form with an aldehyde molecule into
ran-2-ones 11a–f in 50–70% yields (Method A, the corresponding furanone (Scheme 3). Formation of
Scheme 2, Table 1). Surprisingly, neither triazolopyrim- imines like 14 in similar heterocyclizations involving aro-
idines 12, the formation of which was earlier described in matic or heterocyclic amines and pyruvic acids was previ-
the similar multicomponent treatment involving 1-unsub- ously described and discussed in several publications.10
stituted 3-amino-1,2,4-triazole,2a nor pyrrolone deriva- Other possible pathways, for example, via preliminary
tives of type 9, which were produced in the case of treatment of pyruvic acid with aldehyde giving
phenylpyruvic acid reactions,2c were isolated or even arylidenepyruvic acids 13 or whole furanone nucleus are
chromatographically detected in the mother liquor.
doubtful according to our earlier results obtained for anal-
ogous multicomponent reactions.2a,c
Table 1 3-[5-Amino-1-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylami-
no]-5-arylfuran-2-ones 11a–f
Cl
Entry
R
Product
Yield (%)
Method A Method B
8
11
6
+ 10
– H2O
– H2O
OH
1
2
3
4
5
6
Ph
11a
11b
11c
11d
11e
11f
60
63
68
70
50
58
52
48
50
51
47
58
N
N
N
H2N
4-MeOC6H4
4-BrC6H4
4-ClC6H4
4-HO2CC6H4
4-MeC6H4
N
O
14
Cl
R
11
6
+ 13
N
N
– H2O
N
H2N
N
OH
In the case of a sequential reaction via preliminary synthe-
sis of arylidenepyruvic acids, the direction of the treat-
ment was identical to the multicomponent procedure. It
was found that refluxing aminoazole 6 and unsaturated
acids 13a–f in DMF led to the formation of the same triazo-
lylfuranones 11a–f, however, in smaller yields (Method
B, Scheme 2, Table 1).
O
15
Scheme 3
An alternative direction of the heterocyclization leading
to triazolopyrimidines 12 is connected with a loss of aro-
maticity by the aminoazole fragment during the reaction
explaining why this pathway is disfavored (Scheme 2).
The most probable way for the formation of triazolylfura-
nones 11 in this multicomponent reaction includes attack
of one of the NH2 groups on the b-carbonyl group of pyru-
Synthesis 2011, No. 7, 1120–1124 © Thieme Stuttgart · New York

1122
Y. I. Sakhno et al.
PAPER
On the other hand, isolation of triazolylpyrrolones 9 in- The final structure assignment about structures of the
stead of furanones 11, which was observed in the three- compounds synthesized was made on the basis of X-ray
component heterocyclization involving phenylpyruvic diffraction data obtained for single crystal of heterocycle
acid,2c can be explained by the specific influence of the 11c (Figure 2).
phenyl substituent preventing the formation of intermedi-
ate like 14.
In summary, an introduction of aryl substituent in position
1 of aminotriazole affects the direction of multicompo-
It seems that the reaction of aminotriazole 6 with nent reactions with pyruvic acid and aldehydes. In con-
arylidenepyruvic acid 13 can take place via formation of trast to 1-unsubstituted 3,(5)-(di)amino-1,2,4-triazoles
imine 15 and its further cyclization into final heterocycles such treatment involving 1-(4-chlorophenyl)-3,5-diami-
11 (Scheme 3).10e
no-1,2,4-triazole proceeds in an unusual way with forma-
tion of unprecedented 3-[5-amino-1-(4-chlorophenyl)-
1H-1,2,4-triazol-3-ylamino]-5-arylfuran-2-ones instead
of triazolopyrimidine derivatives.
The structure of the compounds 11a–f was established by
elemental analysis, mass spectrometry, 1H and 13C NMR
spectroscopy with application of NOE, and X-ray diffrac-
tion study. For example, 1H NMR spectra of 11a–f exhibit
doublets of two CH groups at 6.0–7.2 ppm (3J = ~2.1–2.5
Hz), signals of aromatic protons (6.5–7.8 ppm), a singlet
of NH group at ca. 9.0 ppm, a broad singlet of NH2 group
at 6.6 ppm, and appropriate signals of terminal substitu-
ents. NOE experiments, in particular, showed the pres-
ence of cross-peaks between NH2 group and the ortho-
proton of the N-aryl substituent (Figure 1) in compound
Melting points were obtained on a standard melting point apparatus
in open capillary tubes. The 1H and 13C NMR spectra were recorded
in DMSO-d6 at 200 MHz (50 MHz for 13C) on Varian Mercury VX-
200 spectrometers. High-resolution mass spectra were measured on
a GC-MS Varian 1200L spectrometer (ionizing voltage 70 eV).
Elemental analysis was made on a EuroVector EA-3000. TLC anal-
yses were performed on precoated (silica gel 60 HF254) plates. All
solvents and chemicals were obtained from standard commercial
11b that allowed to identify which exocyclic amino group vendors and used without any purification.
was involved in the reaction. Signals of protons for both
para-substituted aryl rings were assigned according to
NOE correlations of methoxy group.
3-[5-Amino-1-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamino]-5-
arylfuran-2(5H)-ones 11a–f; General Procedure
Method A: A mixture containing 3,5-diamine-1-(4-chlorophenyl)-
1,2,4-triazole (6; 100 mg, 0.5 mmol), the corresponding aldehyde
8a–f (0.5 mmol) and pyruvic acid (10; 40 mg, 0.03 mL, 0.5 mmol)
in DMF (0.5 mL) was refluxed for 5 min. The reaction mixture was
cooled to r.t. and diluted with EtOH (10 mL). The precipitate
formed was collected by filtration, washed with EtOH (2 mL), and
dried.
H
H
H
O
H
Cl
Method B: A mixture containing 3,5-diamine-1-(4-chlorophenyl)-
1,2,4-triazole (6; 210 mg, 1 mmol) and arylidenepyruvic acid 13a–
f (1 mmol) in DMF (0.7 mL) was refluxed for 5 min. After cooling
to r.t., EtOH (10 mL) was added and the mixture was allowed to
stand overnight. The precipitate formed was isolated by filtration,
washed with EtOH (10 mL), and air-dried.
H
O
O
N
N
H
N
H2N
N
H
Figure 1 Some NOE correlations for compound 11b
3-[5-Amino-1-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamino]-5-
phenylfuran-2(5H)-one (11a)
Yellow solid; mp 212–214 °C.
1H NMR (200 MHz, DMSO-d6): d = 6.16 (d, J = 2.3 Hz, 1 H, CH),
6.58 (br s, 1 H, NH2), 7.07 (d, J = 2.3 Hz, 1 H, CH), 7.24–7.63 (m,
9 H, ArH), 9.02 (s, 1 H, NH).
The regioselectivity of the reaction regarding the NH2
groups is concerned with sterical influence of chlorophe-
nyl substituent on amino group in position 5 hampering its
participation in the treatment.
13C NMR (50 MHz, DMSO-d6): d = 81.9, 102.9, 122.2, 124.3,
127.3, 129.4, 129.9, 131.0, 132.9, 137.1, 137.7, 154.8, 157.8, 169.9.
MS (EI, 70 eV): m/z (%) = 367 (22, [M+]), 323 (25), 153 (100).
Anal. Calcd for C18H14ClN5O2: C, 58.78; H, 3.84; N, 19.04. Found:
C, 58.81; H, 3.84; N, 19.01.
3-[5-Amino-1-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamino]-5-
(4-methoxyphenyl)furan-2(5H)-one (11b)
Yellow solid; mp 210–212 °C.
1H NMR (200 MHz, DMSO-d6): d = 3.73 (s, 3 H, CH3O), 6.11 (d,
J = 2.1 Hz, 1 H, CH), 6.60 (br s, 1 H, NH2), 7.04 (d, J = 2.1 Hz, 1
H, CH), 6.88–7.62 (m, 8 H, ArH), 9.0 (s, 1 H, NH).
13C NMR (50 MHz, DMSO-d6): d = 55.9, 81.8, 114.9, 122.2, 124.2,
Figure 2 Molecular structure of compound 11c (X-ray diffraction
data)
128.2, 129.1, 129.3, 129.9, 131.0, 137.0, 154.7, 157.8, 160.5, 169.9.
MS (EI, 70 eV): m/z (%) = 397 (13, [M+]), 338 (20), 153 (100).
Synthesis 2011, No. 7, 1120–1124 © Thieme Stuttgart · New York

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Unusual Multicomponent Reaction of Aminotriazole with Pyruvic Acid and Aldehydes
1123
Anal. Calcd for C19H16ClN5O3: C, 57.36; H, 4.05; N, 17.6. Found:
C, 57.39; H, 4.02; N, 17.65.
1H NMR (200 MHz, DMSO-d6): d = 2.28 (s, 3 H, CH3), 6.11 (d,
J = 2.1 Hz, 1 H, CH), 6.59 (br s, 1 H, NH2), 7.04 (d, J = 2.1 Hz, 1
H, CH), 7.16–7.59 (m, 8 H, ArH), 9.0 (s, 1 H, NH).
3-[5-Amino-1-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamino]-5-
(4-bromophenyl)furan-2(5H)-one (11c)
Yellow solid; mp 208–210 °C.
1H NMR (200 MHz, DMSO-d6): d = 6.16 (d, J = 2.1 Hz, 1 H, CH),
6.55 (br s, 1 H, NH2), 7.06 (d, J = 2.1 Hz, 1 H, CH), 7.22–7.67 (m,
8 H, ArH), 8.98 (s, 1 H, NH).
13C NMR (50 MHz, DMSO-d6): d = 21.4, 81.9, 122.2, 122.3, 124.3,
127.4, 128.1, 129.9, 130.0, 134.6, 137.1, 139.0, 154.7, 157.8, 169.9.
MS (EI, 70 eV): m/z (%) = 381 (37, [M+]), 337 (47), 194 (43).
Anal. Calcd for C19H16ClN5O2: C, 59.77; H, 4.22; N, 18.34. Found:
C, 59.73; H, 4.19; N, 18.31.
13C NMR (50 MHz, DMSO-d6): d = 81.1, 121.7, 122.6, 124.4,
128.3, 129.5, 129.9, 131.1, 132.4, 137.1, 137.2, 154.8, 157.7, 169.7.
MS (EI, 70 eV): m/z (%) = 445 (12, [M+]), 252 (20), 153 (100).
References
(1) (a) Chebanov, V. A.; Gura, K. A.; Desenko, S. M. Top.
Heterocycl. Chem. 2010, 23, 41. (b) Chebanov, V. A.;
Desenko, S. M.; Gurley, T. W. Azaheterocycles Based on
a,b-Unsaturated Carbonyls; Springer: Meppel, 2008.
(2) (a) Chebanov, V. A.; Sakhno, Ya. I.; Desenko, S. M.;
Shishkina, S. V.; Musatov, V. I.; Shishkin, O. V.; Knyazeva,
I. V. Synthesis 2005, 2597. (b) Chebanov, V. A.; Sakhno,
Ya. I.; Desenko, S. M.; Chernenko, V. N.; Musatov, V. I.;
Shishkina, S. V.; Shishkin, O. V.; Kappe, C. O. Tetrahedron
2007, 63, 1229. (c) Sakhno, Ya. I.; Desenko, S. M.;
Shishkina, S. V.; Shishkin, O. V.; Sysoyev, D. O.; Groth, U.;
Kappe, C. O.; Chebanov, V. A. Tetrahedron 2008, 64,
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Musatov, V. I.; Vashchenko, E. V.; Desenko, S. M.;
Chebanov, V. A. Mol. Diversity 2010, 14, 523.
Anal. Calcd for C18H13BrClN5O2: C, 48.4; H, 2.93; N, 15.68.
Found: C, 48.37; H, 2.9; N, 15.64.
X-ray Diffraction Analysis
The colorless crystals of 11c (C18H13BrClN5O2·C2H6OS) are mono-
clinic. At 293 K, a = 19.7450(8), b = 5.4916(3), c = 21.8240(9) Å,
b = 106.709(5)°, V = 2266.5(2) Å3, Mr = 524.82, Z = 4, space
group P21/n, dcalc = 1.538 g/cm3, m(MoKa) = 2.056 mm–1,
F(000) = 1064. Intensities of 7131 reflections (3776 independent,
Rint = 0.040) were measured on the ‘Xcalibur-3’ diffractometer
(graphite monochromated MoKa radiation, CCD detector, w-scan-
ing, 2qmax = 50°). The structure was solved by direct method using
SHELXTL package.11 The absorption correction was performed by
multiscan method (Tmin = 0.578, Tmax = 0.904). Positions of the hy-
drogen atoms were located from electron density difference maps
and refined by ‘riding’ model with Uiso = nUeq of the carrier atom
(n = 1.5 for methyl groups and n = 1.2 for other hydrogen atoms).
Full-matrix least-squares refinement against F2 in anisotropic ap-
proximation for non-hydrogen atoms using 3737 reflections was
converged to wR2 = 0.154 [R1 = 0.054 for 1597 reflections with
F>4s(F), S = 0.859].12
(3) (a) Chebanov, V. A.; Saraev, V. E.; Desenko, S. M.;
Chernenko, V. N.; Shishkina, S. V.; Shishkin, O. V.; Kobzar,
K. M.; Kappe, C. O. Org. Lett. 2007, 9, 1691.
(b) Chebanov, V. A.; Saraev, V. E.; Desenko, S. M.;
Chernenko, V. N.; Knyazeva, I. V.; Groth, U.; Glasnov, T.
N.; Kappe, C. O. J. Org. Chem. 2008, 73, 5110.
(c) Muravyova, E. A.; Shishkina, S. V.; Musatov, V. I.;
Shishkin, O. V.; Desenko, S. M.; Chebanov, V. A. Synthesis
2009, 1375.
3-[5-Amino-1-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamino]-5-
(4-chlorophenyl)furan-2(5H)-one (11d)
Yellow solid; mp 222–224 °C.
1H NMR (200 MHz, DMSO-d6): d = 6.18 (d, J = 2.2 Hz, 1 H, CH),
6.56 (br s, 1 H, NH2), 7.07 (d, J = 2.2 Hz, 1 H, CH), 7.28–7.65 (m,
8 H, ArH), 9.0 (s, 1 H, NH).
13C NMR (50 MHz, DMSO-d6): d = 81.1, 121.7, 124.3, 128.4,
129.2, 129.5, 129.9, 131.1, 134.2, 136.7, 137.1, 154.7, 157.7, 169.7.
MS (EI, 70 eV): m/z (%) = 401 (16, [M+]), 357 (20), 194 (27), 153
(100).
(4) (a) Lipson, V. V.; Desenko, S. M.; Borodina, V. V.;
Shirobokova, M. G.; Musatov, V. I. Russ. J. Org. Chem.
2005, 41, 114. (b) Chernyshev, V. M.; Sokolov, A. N.;
Taranushich, V. A. Russ. J. Appl. Chem. 2007, 80, 1691.
(5) (a) Chernyshev, V. M.; Astakhov, A. V.; Starikova, Z. A.
Tetrahedron 2010, 66, 3301. (b) Chernyshev, V. M.;
Rakitov, V. A.; Taranushich, V. A.; Blinov, V. V. Chem.
Heterocycl. Compd. 2005, 41, 1139. (c) Chernyshev, V. M.;
Kosov, A. E.; Gladkov, E. S.; Shishkina, S. V.; Taranushich,
V. A.; Desenko, S. M.; Shishkin, O. V. Russ. Chem. Bull.,
Int. Ed. 2006, 55, 338. (d) Chernyshev, V. M.; Rakitov, V.
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A.; Blinov, V. V.; Taranushich, V. A.; Starikova, Z. A.
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Anal. Calcd for C18H13Cl2N5O2: C, 53.75; H, 3.26; N, 17.63. Found:
C, 53.71; H, 3.22; N, 17.61.
4-{4-[5-Amino-1-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamino]-
5-oxo-2,5-dihydrofuran-2-yl}benzoic Acid (11e)
Yellow solid; mp 258–260 °C.
1H NMR (200 MHz, DMSO-d6): d = 6.26 (d, J = 1.8 Hz, 1 H, CH),
6.59 (br s, 1 H, NH2), 7.1 (d, J = 1.8 Hz, 1 H, CH), 7.33–8.07 (m, 8
H, ArH), 9.1 (s, 1 H, NH), 12.99 (br s, 1 H, CO2H).
(6) (a) Papini, P. Gazz. Chim. Ital. 1950, 80, 100. (b)Papini,P.;
Checchi, S. Gazz. Chim. Ital. 1950, 80, 850. (c) Papini, P.
Gazz. Chim. Ital. 1952, 82, 735.
(7) Bavley, A. US Patent 2 406 654, 1946; Chem. Abstr. 1947,
41, 42h.
13C NMR (50 MHz, DMSO-d6): d = 81.2, 122.0, 124.3, 127.4,
128.1, 129.9, 130.5, 130.9, 131.8, 136.9, 142.4, 154.6, 157.7, 167.5,
169.8.
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(9) For reviews and related papers on multicomponent reactions
see, for example: (a) Multicomponent Reactions; Zhu, J.;
Bienayme, H., Eds.; Wiley-VCH: Weinheim, 2005.
(b) Biggs-Houck, J. E.; Younai, A.; Shaw, J. T. Curr. Opin.
Chem. Biol. 2010, 14, 371. (c) Ganem, B. Acc. Chem. Res.
2009, 42, 463. (d) Sunderhaus, J. D.; Martin, S. F. Chem.
MS (EI, 70 eV): m/z (%) = 411 (2, [M+]), 367 (5), 209 (61).
Anal. Calcd for C19H14ClN5O4: C, 55.42; H, 3.43; N, 17.01. Found:
C, 55.38; H, 3.39; N, 17.05.
3-[5-Amino-1-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamino]-5-
p-tolylfuran-2(5H)-one (11f)
Yellow solid; mp 216–218 °C.
Synthesis 2011, No. 7, 1120–1124 © Thieme Stuttgart · New York

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Y. I. Sakhno et al.
PAPER
Eur. J. 2009, 15, 1300. (e) Isambert, N.; Lavilla, R. Chem.
Eur. J. 2008, 14, 8444.
(11) Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112.
(12) The final atomic coordinates, and crystallographic data for
molecule 11c have been deposited to with the Cambridge
Crystallographic Data Centre, 12 Union Road, CB2 1EZ,
UK [fax: +44(1223)336033; e-mail:
(10) (a) Tapia, I.; Alcazar, V.; Moran, J. R.; Grande, M. Bull.
Chem. Soc. Jpn. 1990, 63, 2408. (b) Ghavtadze, N.;
Fröhlich, R.; Würthwein, E. U. Eur. J. Org. Chem. 2008,
3656. (c) Abasolo, M. I.; Gaozza, C. H.; Fernandez, B. M.
J. Heterocycl. Chem. 1987, 24, 1771. (d) Liu, K. C.; Shih,
B. J.; Lee, C. H. J. Heterocycl. Chem. 1992, 29, 97.
(e) Groenendaal, B.; Ruijter, E.; Orru, R. V. A. Chem.
Commun. 2008, 5474.
deposit@ccdc.cam.ac.uk] and are available on request
quoting the deposition number CCDC 793788.
Synthesis 2011, No. 7, 1120–1124 © Thieme Stuttgart · New York