Synthesis and opening of the thiadiazine ring in 6,7-dihydro-5H-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazines

Article abstract of DOI:10.1007/s11172-008-0164-y

A reaction of 3-benzylthiotriazole-4-amines with aromatic aldehydes leads to the formation of 6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines. A dihydrothiadiazine ring opening along the N-N bond occurs by the action of strong bases.

Full text of DOI:10.1007/s11172-008-0164-y

Russian Chemical Bulletin, International Edition, Vol. 57, No. 6, pp. 1273—1276, June, 2008
1273
Synthesis and opening of the thiadiazine
ring in 6,7ꢀdihydroꢀ5Hꢀ[1,2,4]triazolo[3,4ꢀb][1,3,4]thiadiazines
A. A. Kolodina, N. I. Gaponenko, and A. V. Lesin
South Federal University, Department of Chemistry,
7 ul. Zorge, 344090 RostovꢀonꢀDon, Russian Federation.
Fax: +7 (863) 26 6567. Eꢀmail: lexandra@inbox.ru
A reaction of 3ꢀbenzylthiotriazoleꢀ4ꢀamines with aromatic aldehydes leads to the formation of
6,7ꢀdihydroꢀ5Hꢀ[1,2,4]triazolo[3,4ꢀb][1,3,4]thiadiazines. A dihydrothiadiazine ring opening along
the N—N bond occurs by the action of strong bases.
Key words: [1,2,4]triazolo[3,4ꢀb][1,3,4]thiadiazines, dihydrothiadiazine, annulation, ring openꢀ
ing, 2ꢀ[(1,2,4ꢀtriazolꢀ3ꢀyl)thio]ethanimine, Xꢀray crystallography.
Earlier,1 we reported on a new thermoinduced inꢀ
Scheme 1
tramolecular cyclization of thiomethyleneꢀactive derivaꢀ
tives of Nꢀquinoneiminoꢀoꢀaminothiophenols, in the
course of which spiroconjugated benzothiazines are
formed. The present work is aimed at the study of possiꢀ
bilities of intramolecular cyclization of thiomethyleneꢀ
active derivatives of aminothiotriazoles, the heterocyclic
analogs of oꢀaminothiophenols.
A baseꢀcatalyzed condensation of 3ꢀ[(4ꢀnitrobenꢀ
zyl)thio]ꢀ5ꢀRꢀ1,2,4ꢀtriazolꢀ4ꢀamines 1a—c with aromatꢀ
ic aldehydes leads to 6,7ꢀdihydroꢀ5Hꢀtriazolo[3,4ꢀb]ꢀ
[1,3,4]thiadiazines 2. In the absence of electronꢀwithꢀ
drawing NO2 group in the thiobenzylic fragment, the
heterocyclization does not take place and the reaction
stops after formation of imine 3 (Scheme 1).
A dependence of the cyclization course on the presꢀ
ence of a base in the reaction medium and on the lability of
the thiomethylene protons allows one to suggest that the meꢀ
chanism of the thiadiazine ring formation includes elimꢀ
ination of the proton of the methylene group activated by
the electronꢀwithdrawing substituent followed by the nuꢀ
cleophilic attack of the carbanionic center formed at the
C atom of the azomethine group, in the course of which
the C(6)—C(7) bond of triazolothiadiazine 2 is formed.
The formation of compounds 2 is confirmed by the
transformation of the signals for the methylene and amiꢀ
1: Ar´ = 4ꢀNO2C6H4 (a—c), Ph (d);
R = 3ꢀC5H4N (a), Ph (b), 4ꢀC5H4N (c, d);
2: Ar´ = 4ꢀNO2C6H4 (a—e);
R = 3ꢀC5H4N (a), Ph (b, c), 4ꢀC5H4N (d, e);
Ar = 4ꢀBrC6H4 (a, b, e), 4ꢀNO2C6H4 (c), 3ꢀNO2C6H4 (d);
3: R = 4ꢀC5H4N, Ar = 4ꢀBrC6H4, Ar´ = Ph
pounds 4a,b, which display solvatochromic properties
(Scheme 2).
1
no groups in the H NMR spectrum of the starting comꢀ
In the mass spectrum of compound 4a, a peak of the
molecular ion is observed, which corresponds to the
weight of this compound and the starting triazolothiadiꢀ
azine 2a. In the 1H NMR spectra of compounds 4 recordꢀ
ed in deuterochloroform, there are a twoꢀproton singlet
at δ 5.2 and a oneꢀproton singlet at δ 11.2. At the same
time, when DMSOꢀd6 was used as the solvent, two oneꢀ
proton singlets at δ 6.6 and 6.9 and a oneꢀproton singlet at
δ 14.0 can be observed in the spectrum. Signals in
pound 1 into the oneꢀproton signals of the vicinal protons
of two CH groups and the NH group of the thiadiazine
ring. The sharp resolution of the signals for H(6) and
H(7) and the value of their spinꢀspin coupling constants
(J = 10 Hz) attest the diastereoselectivity of the process of
the thiadiazines 2 formation.
The synthesized dihydroꢀ1,2,4ꢀtriazolothiadiazines
2a,b under the action of strong bases give comꢀ
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1249—1252, June, 2008.
1066ꢀ5285/08/5706ꢀ01273 © 2008 Springer Science+Business Media, Inc.

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Kolodina et al.
Scheme 2
B is a base
the aromatic region of these spectra attest the presꢀ
ence of 3ꢀpyridyl (phenyl) and both pꢀsubstituted aroꢀ
matic rings. Taking into account the spectral data obꢀ
tained, the two structures 4 and 4´ can be suggested as
the most probable, which are isomeric to the molecules
of starting triazolothiadiazines 2. In our view, the solvaꢀ
tochromic properties are caused by the mutual transforꢀ
mations of the amino and imino tautomers in different
solvents.
gative charge in the triazole ring by the cleavage of
the N—N bond.
The Xꢀray data confirmed the structure of compound
4´a (Fig. 1).
The pyridine and triazole rings of the molecule 4´a
are in the same plane. In the triazole fragment, the nitꢀ
rogen atom N(2) of the pyrrole type has virtually
the planar configuration (it comes out of the plane of
the triazole ring by 0.022 Å). The C(2)=C(1) bond is
oriented away from the triazole ring (the torsional angle
C(1)—C(2)—S(1)—C(3) is equal to 113.0(5)°), its
length is 1.375(7) Å. The cisꢀsubstituents, pꢀNO2ꢀ and
A suggested mechanism of the thiadiazine ring openꢀ
ing includes elimination of the proton H(6) and formaꢀ
tion of anion 5 with further stabilization of the neꢀ
O(1)
N(5)
O(2)
C(20)
C(19)
C(18)
C(17)
C(21)
C(16)
C(15)
C(10)
C(14)
Br(1)
S(1)
C(9)
C(7)
N(1)
N(4)
C(8)
C(1)
C(5)
C(6)
C(2)
C(13)
C(12)
C(3)
C(4)
N(6)
N(2)
C(11)
N(3)
H(2N(6))
O(1W)
H(1N(6))
H(2W)
H(1W)
Fig. 1. The Xꢀray data on the structure of molecule 4´a.

Triazolothiadiazine ring opening reaction
Russ.Chem.Bull., Int.Ed., Vol. 57, No. 6, June, 2008
1275
3ꢀ(4ꢀNitrobenzyl)thioꢀ5ꢀphenylꢀ4Hꢀ1,2,4ꢀtriazoleꢀ4ꢀamine
(1b). The yield was 73%, m.p. 209 °C. Found (%): C, 55.12;
H, 4.01; N, 21.29. C15H13N5O2S. Calculated (%): C, 55.00;
H, 3.98; N, 21.40. 1H NMR (CDCl3), δ: 4.47, 4.52 (both s, 2 H each,
SCH2, NH2); 7.46 (m, 3 H, Ph); 7.62, 8.16 (both d, 2 H each, Ar,
J = 8.5 Hz); 7.93 (m, 2 H, Ph).
3ꢀ(4ꢀNitrobenzyl)thioꢀ5ꢀ(pyridinꢀ4ꢀyl)ꢀ4Hꢀ1,2,4ꢀtriazoleꢀ4ꢀ
amine (1c). The yield was 70%, m.p. 218—220 °C. Found (%):
C, 51.15; H, 3.67; N, 25.67. C14H12N6O2S. Calculated (%):
C, 51.20; H, 3.66; N, 25.60. 1H NMR (CDCl3), δ: 4.58 (s, 4 H,
SCH2, NH2); 7.64, 8.16 (both d, 2 H each, Ar, J = 8.5 Hz); 8.03,
8.72 (both d, 2 H each, Py, J = 6.2 Hz).
pꢀBrꢀphenyl fragments are turned with respect to the plane
of the C(2)=C(1) bond by ~40°: the torsional angle
C(2)—C(1)—C(10)—C(15) is equal to 47.0(7)°, whereꢀ
as the angle C(17)—C(16)—C(2)—C(1) to 38.0(8)°.
In conclusion, we suggested a new method for the
annulation of dihydrothiadiazine ring to aminothiotriꢀ
azoles, a distinguishing feature of which is the formation
of the carbon—carbon bond in the final step of the hetꢀ
erocyclization. The triazolothiadiazines that formed by
the action of a strong base are able to undergo the opening
of the hydrogenated heterocycle along the N—N bond,
which leads to triazolylthioethanimines.
3ꢀBenzylthioꢀ5ꢀ(pyridinꢀ4ꢀyl)ꢀ4Hꢀ1,2,4ꢀtriazolꢀ4ꢀamine (1d).
The yield was 73%, m.p. 186—188 °C. Found (%): C, 58.75;
H, 3.87; N, 25.18. C14H13N5S. Calculated (%): C, 59.34; H, 4.62;
Experimental
1
N, 24.72. H NMR (DMSOꢀd6), δ: 4.46 (s, 2 H, SCH2); 6.23
(s, 2 H, NH2); 7.26—7.35 (m, 3 H, Ph); 7.47 (d, 2 H, Ph); 7.99,
8.72 (both d, 2 H each, Py, J = 6.1 Hz).
1
H NMR spectra were recorded on a Varian Unityꢀ300
(300 MHz) and Bruker DPXꢀ250 (250 MHz) spectrometers at
25 °C with Me4Si as the internal standard. Mass spectra were
recorded on a Finnigan MAT INCOS 50 instrument.
Triazolothiadiazines 2a—e (general procedure). Equimolar
amounts (5 mmol) of compound 1 and aromatic aldehyde were
refluxed for 1—1.5 h in EtOH (10 mL) with catalytic amount of
NaOH. After cooling, the reaction mixture was diluted with water,
a precipitate was filtered off and recrystallized from MeCN.
6ꢀ(4ꢀBromophenyl)ꢀ7ꢀ(4ꢀnitrophenyl)ꢀ3ꢀ(pyridinꢀ3ꢀyl)ꢀ6,7ꢀ
dihydroꢀ5Hꢀ[1,2,4]triazolo[3,4ꢀb][1,3,4]thiadiazine (2a). The
yield was 65%, m.p. 280—282 °C. Found (%): C, 51.83; H, 3.88;
N, 16.31. C22H19BrN6O2S. Calculated (%): C, 51,67; H, 3.74;
N, 16.43. 1H NMR (DMSOꢀd6), δ: 5.02 (dd, 1 H, H(6), J = 10.2 Hz,
J = 10.3 Hz); 5.25 (d, 1 H, H(7), J = 10.2 Hz); 7.24, 7.45 (both d,
2 H each, Ar, J = 8.1 Hz); 7.5 (m, 1 H, Py); 7.55 (d, 1 H, NH,
J = 10.3 Hz); 7.70, 8.11 (both d, 2 H each, Ar, J = 8.5 Hz); 8.29
(d, 1 H, Py, J = 7.9 Hz); 8.65 (d, 1 H, Py, J = 4.1 Hz); 9.1 (s, 1 H,
Py). MS (EI, 70 eV), m/z (Irel (%)): 329 (3), 319 (22), 294 (10), 196
(32), 178 (60), 165 (25), 149 (23), 104 (83), 89 (100), 76 (80).
6ꢀ(4ꢀBromophenyl)ꢀ7ꢀ(4ꢀnitrophenyl)ꢀ3ꢀphenylꢀ6,7ꢀdihydroꢀ
5Hꢀ[1,2,4]triazolo[3,4ꢀb][1,3,4]thiadiazine (2b). The yield was
79%, m.p. 280 °C. Found (%): C, 53.26; H, 3.09; N, 14.00.
C22H16BrN5O2S. Calculated (%): C, 53.45; H, 3.26; N, 14.17.
1H NMR (DMSOꢀd6), δ: 5.0 (dd, 1 H, H(6), J = 10.0 Hz,
J = 10.4 Hz); 5.2 (d, 1 H, H(7), J = 10.0 Hz); 7.26 (d, 2 H, Ar,
J = 8.4 Hz); 7.42—7.47 (m, 5 H, Ph, Ar); 7.51 (d, 1 H, NH,
J = 10.4 Hz); 7.71, 8.11 (both d, 2 H each, Ar, J = 8.6 Hz);
7.91—7.97 (m, 2 H, Ph). MS (EI, 70 eV), m/z (Irel (%)): 495 [M]+
(4), 493 [M]+ (4), 461 (2), 360 (5), 328 (13), 312 (27), 196 (48),
177 (99), 149 (65), 105 (100), 77 (98).
Monocrystals of compound 4´a were obtained by crystallization
from acetonitrile. The Xꢀray analysis of compound 4´a (the experiꢀ
mental set of 2659 reflections) was obtained on a Syntex P21
diffractometer at 193 K (graphite monochromator, λ(MoꢀKα)ꢀirradiꢀ
ation, 2θmax = 54°), the monocrystal size was 0.40×0.25×0.15 mm.
When the equivalent reflections were averaged, 2530 independent
reflections were obtained (Rint = 0.0238), which were used for
decoding and refining of the structure. Absorption (μ = 20.06 cm–1
)
was not considered. The red plateꢀlike crystals C21H17BrN6O3S,
M = 513.38, monoclinic. At 193 K, a = 10.252(2) Å, b = 10.073(3) Å,
c = 10.648(3) Å, α = 90°, β = 94.335(18)°, γ = 90°, V = 1096.5(5) Å3,
the space group P2(1), Z = 2, dcalc = 1.555 g cm–3. The structure
was solved by the direct method, all the nonhydrogen atoms were
localized in the differential syntheses of electron density and refined
on F 2hkl in anisotropic approximation; all the hydrogen atoms were
placed into the geometrically calculated positions and considered
during refining by the riding model with U(H) = nU(C), where
U(C) is the equivalent temperature factor of the C atom, which the
corresponding H atom is bonded to, n = 1.2 and 1.5 for the carbon
atoms Csp2 and Csp3, respectively. The final value of nonauthenticity
factors: R1 = 0.0436 (calculated on Ffor 1889 reflections with I> 2σ(I),
wR2 = 0.0947 (calculated on F2 for all the 2530 reflections),
hkl
GOF = 1.003, 289 refining parameters. All the calculations were
made with the use of the SHELXTL PLUS 5 program package.2
3ꢀThioꢀ5ꢀRꢀ1,2,4ꢀtriazolꢀ4ꢀamines were obtained according
to the procedure described earlier.3
3ꢀBenzylthioꢀ1,2,4ꢀtriazoles 1a—c (general procedure).
4ꢀAminoꢀ5ꢀRꢀ1,2,4ꢀtriazoleꢀ3ꢀthiol (10 mmol) was added to
a solution of NaOH (10 mmol) in MeOH (15 mL). After dissolution
of the triazole, pꢀnitrobenzyl bromide or benzyl bromide (10 mmol)
was added. After several minutes, a formation of thick white precipꢀ
itate was observed, which was filtered off, washed with water, and
recrystallized from EtOH.
6,7ꢀDi(4ꢀnitrophenyl)ꢀ3ꢀphenylꢀ6,7ꢀdihydroꢀ5Hꢀ[1,2,4]triꢀ
azolo[3,4ꢀb][1,3,4]thiadiazine (2c). The yield was 38%, m.p.
260 °C. Found (%): C, 57.63; H, 3.72; N, 18.11. C22H16N6O4S.
Calculated (%): C, 57.39; H, 3.50; N, 18.25. 1H NMR (DMSOꢀd6),
δ: 5.18—5.35 (m, 2 H, H(6), H(7)); 7.46 (m, 3 H, Ph); 7.58 (d, 2 H,
Ar, J = 8.8 Hz); 7.67 (d, 1 H, NH, J = 10.1 Hz); 7.74 (d, 2 H, Ar,
J = 8.7 Hz); 7.95 (m, 2 H, Ph); 8.12 (m, 4 H, Ar). MS (EI, 70 eV),
m/z (Irel (%)): 293 (2), 285 (3), 249 (2), 190 (7), 177 (27), 165 (15),
149 (19), 118 (23), 103 (100), 76 (77).
3ꢀ(4ꢀNitrobenzyl)thioꢀ5ꢀ(pyridinꢀ3ꢀyl)ꢀ4Hꢀ1,2,4ꢀtriazoleꢀ4ꢀ
amine (1a). The yield was 86%, m.p. 215 °C. Found (%): C, 51.37;
H, 3.79; N, 25.76. C14H12N6O2S. Calculated (%): C, 51.20;
H, 3.66; N, 25.60. 1H NMR (CDCl3), δ: 4.53, 4.57 (both s,
2 H each, SCH2, NH2); 7.41 (m, 1 H, Py); 7.63, 8.16 (both d,
2 H each, Ar, J = 8.8 Hz); 8.35 (d, 1 H, Py, J = 8.1 Hz); 8.69
(d, 1 H, Py, J = 5.0 Hz); 9.29 (s, 1 H, Py).
6ꢀ(3ꢀNitrophenyl)ꢀ7ꢀ(4ꢀnitrophenyl)ꢀ3ꢀ(pyridinꢀ4ꢀyl)ꢀ6,7ꢀdiꢀ
hydroꢀ5Hꢀ[1,2,4]triazolo[3,4ꢀb][1,3,4]thiadiazine (2d). The yield
was 34%, m.p. 180—182 °C. Found (%): C, 55.56; H, 4.14;
N, 20.37. C22H19N7O4S. Calculated (%): C, 55.34; H, 4.01;
N, 20.53. 1H NMR (DMSOꢀd6), δ: 5.27 (dd, 1 H, H(6), J = 10.1
Hz, J = 10.0 Hz); 5.40 (d, 1 H, H(7), J = 9.6 Hz); 7.57 (dd, 1 H, Ar,
J = 7.7 Hz, J = 8.1 Hz); 7.67—7.77 (m, 3 H, Ar); 7.80 (d, 1 H, NH,

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Kolodina et al.
J = 10.0 Hz); 7.97 (d, 2 H, Py, J = 6.2 Hz); 8.05—8.17 (m, 3 H, Ar);
8.26 (s, 1 H, Ar); 8.71 (d, 2 H, Py, J = 6.1 Hz). MS (EI, 70 eV), m/z
(Irel (%)): 295 (3), 284 (3), 264 (2), 191 (4), 178 (20), 165 (13), 149
(27), 104 (68), 89 (83), 78 (82), 51 (100).
1H NMR (CDCl3), δ: 5.25 (s, 2 H, NH2); 7.05—7.61 (m, 7 H, Ar);
7.91 (d, 2 H, Ar, J = 8.5 Hz); 8.28 (d, 1 H, Py, J = 7.9 Hz); 8.65
(d, 1 H, Py, J = 4.1 Hz); 9.25 (s, 1 H, Py); 11.34 (s, 1 H, NH,
triazole). MS (EI, 70 eV), m/z (Irel (%)): 494 [M]+ (7), 461 (12),
318 (43), 193 (35), 183 (100), 165 (48), 102 (86), 76 (75), 44 (92).
1ꢀ(4ꢀBromophenyl)ꢀ2ꢀ(4ꢀnitrophenyl)ꢀ2ꢀ(5ꢀphenylꢀ1Hꢀ
1,2,4ꢀtriazolꢀ3ꢀylthio)ethanimine (4b). The yield was 92%, m.p.
121 °C. Found (%): C, 53.72; H, 3.56; N, 14.02. C22H16BrN5O2S.
Calculated (%): C, 53.45; H, 3.26; N, 14.17. 1H NMR (DMSOꢀd6),
δ: 6.66 (s, 1 H, SCH); 6.94 (s, 1 H, NH, imine); 7.19—7.62 (m, 9 H,
Ar); 7.81—7.95 (m, 4 H, Ar); 13.75 (s, 1 H, NH, triazole). 1H NMR
(CDCl3), δ: 5.18 (s, 2 H, NH2); 7.16, 7.28 (both d, 2 H each, Ar,
J = 8.35 Hz); 7.35—7.47 (m, 5 H, Ar); 7.83—7.93 (m, 4 H, Ar);
11.34 (s, 1 H, NH, triazole). MS (EI, 70 eV), m/z (Irel (%)): 495
[M]+ (1.3), 493 [M]+ (1.7), 462 (4), 312 (12), 223 (12), 185 (22),
183 (23), 165 (21), 104 (100), 77 (61).
6ꢀ(4ꢀBromophenyl)ꢀ7ꢀ(4ꢀnitrophenyl)ꢀ3ꢀ(pyridinꢀ4ꢀyl)ꢀ6,7ꢀ
dihydroꢀ5Hꢀ[1,2,4]triazolo[3,4ꢀb][1,3,4]thiadiazine (2e). The
yield was 52%, m.p. 278 °C. Found (%): C, 51.81; H, 3.86;
N, 16.24. C22H19BrN6O2S. Calculated (%): C, 51,67; H, 3.74;
N, 16.43. 1H NMR (DMSOꢀd6), δ: 5.02 (dd, 1 H, H(6), J = 10.6 Hz,
J = 10.0 Hz); 5.27 (d, 1 H, H(7), J = 9.7 Hz); 7.27, 7.49 (both d,
2 H each, Ar, J = 8.4 Hz); 7.63 (d, 1 H, NH, J = 10.4 Hz); 7.73,
8.13 (both d, 2 H each, Ar, J = 8.7 Hz); 7.98, 8.71 (both d,
2 H each, Py, J = 5.8 Hz). MS (EI, 70 eV), m/z (Irel (%)): 319 (3),
313 (5), 280 (2), 196 (6), 178 (28), 162 (10), 149 (16), 104 (57), 89
(100), 78 (79), 50 (82).
3ꢀ(Benzylthio)ꢀNꢀ[(4ꢀbromophenyl)methylidene]ꢀ5ꢀ(4ꢀpyriꢀ
dinꢀ4ꢀyl)ꢀ4Hꢀ1,2,4ꢀtriazoleꢀ4ꢀamine (3) was recrystallized from
EtOH. The yield was 64%, m.p. 170 °C. Found (%): C, 57.24;
H, 4.41; N, 15.63. C21H16BrN5S. Calculated (%): C, 56.01;
H, 3.58; N, 15.55. 1H NMR (DMSOꢀd6), δ: 4.45 (s, 2 H, SCH2);
7.25—7.32 (m, 5 H, Ph); 7.79—7.87 (m, 6 H, Ar); 8.71 (d, 2 H, Py,
J = 6.3 Hz); 8.82 (s, 1 H, N=CH).
This work was financially supported by the Russian
Foundation for Basic Research (Project No. 05ꢀ03ꢀ32534)
and by the Russian Federation President Council for
Grants (Program for the State Support of Leading Scienꢀ
tific Schools, Grant NShꢀ4849.2006.3).
(Triazolꢀ3ꢀylthio)ethanimines (ethenamines) 4a,b (general proꢀ
cedure). Triazolothiadiazine 2a or 2b (1 mmol) was dissolved in
DMF (5 mL), a solution of EtONa (4 mmol) in EtOH was added
dropwise. After 15 min, the reaction mixture was diluted with water
and neutralized with diluted AcOH. An orange precipitate formed
was filtered off. The product was isolated by column chromatograꢀ
phy (Al2O3, eluent: CHCl3—CH3CN, 5 : 1).
1ꢀ(4ꢀBromophenyl)ꢀ2ꢀ(4ꢀnitrophenyl)ꢀ2ꢀ[5ꢀ(pyridinꢀ3ꢀyl)ꢀ
1Hꢀ1,2,4ꢀtriazolꢀ3ꢀylthio]ethanimine (4a). The yield was 87%,
m.p. 125—127 °C. Found (%): C, 51.21; H, 3.28; N, 16.69.
C21H15BrN6O2S. Calculated (%): C, 50.92; H, 3.05; N, 16.97.
1H NMR (DMSOꢀd6), δ: 6.61 (s, 1 H, SCH); 6.9 (s, 1 H, NH,
imine); 7.18—7.36 (m, 4 H, Ar); 7.45—7.73 (m, 3 H, Ar); 7.89
(d, 2 H, Ar, J = 8.5 Hz); 8.25 (d, 1 H, Py, J = 7.9 Hz); 8.61 (d, 1 H,
Py, J = 4.1 Hz); 9.1 (s, 1 H, Py); 14.04 (s, 1 H, NH, triazole).
References
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Kurbatov, Ros. Khim. Zh., 2004, 48, 103 [Mendeleev Chem. J.,
2004, 48, No. 1 (Engl. Transl.)].
2. G. M. Sheldrick, SHELXTL v 5.10, Structure Determination
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3. J. R. Reid, N. D. Heindel, J. Heterocycl. Chem., 1976, 13, 925.
Received October 3, 2007;
in revised form December 24, 2007