[1,2,4]Triazolo[3,4-b][1,3,4]thiadiazole derivatives containing L-amino acid moieties 213
(s, 2H), 2.40–2.43 (m, 1H), 2.02–2.12 (m, 1H), 1.40–1.55 (m, 1H),
58.1, 29.7, 20.0, 19.5. Anal. Calcd for C32H25N9O4S2: C, 57.91; H,
3.80; N, 18.99; S, 9.66. Found: C, 57.64; H, 3.69; N, 18.72; S, 9.51.
0.92 (d, 6H, J=4.2 Hz); 13C NMR: δ 170.1, 167.6, 158.0, 155.3, 144.1,
135.6, 131.3, 130.0, 124.2, 122.0, 115.3, 59.6, 49.5, 24.9, 23.1, 21.6.
Anal. Calcd for C23H21N5O3S: C, 61.73; H, 4.73; N, 15.65; S, 7.17.
Found: C, 61.59; H, 4.66; N, 15.49; S, 6.94.
2-[3-Methyl-1-(3-(phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]-
thiadiazol-6-yl)butyl]-5-[3-(phenoxymethyl)-[1,2,4]triazolo[3,4-
b][1,3,4]thiadiazol-6-yl]isoindoline-1,3-dione (7e) Yield 90%;
mp 152–154°C; [α]22 =-30° (c=0.02, DMSO); IR: ν 3070, 2958,
General procedure for preparation of compounds (7a–e)
D
1776, 1722, 1599, 1238, 1080 cm-1; 1H NMR: δ 7.24–7.36 (m, 5H),
7.13–7.16 (m, 3H), 6.93–7.05 (m, 5H), 5.82 (dd, 1H, J=10.0 and
4.6 Hz), 5.61 (s, 2H), 5.49 (s, 2H), 2.47 (m, 1H), 2.01 (m, 1H), 1.80
(m, 1H), 0.93 (d, 6H, J=5.8 Hz); 13C NMR: δ 169.7, 166.7, 166.5,
165.9, 158.1, 158.0, 155.2, 154.9, 144.5, 144.0, 135.0, 134.2, 133.9,
132.6, 130.1, 130.0, 125.3, 122.1, 122.0, 115.4, 115.3, 59.6, 49.9,
24.9, 23.0, 21.6. Anal. Calcd for C33H27N9O4S2: C, 58.48; H, 4.02;
N, 18.60; S, 9.46. Found: C, 58.26; H, 3.91; N, 18.53; S, 9.31.
A mixture of triazole 3 (2 mmol) and dicarboxylic acid 6a–e
(1 mmol) in POCl3 (7 mL) was heated under reflux for 16 h, then
slowly poured onto crashed ice with stirring, and neutralized with
solid potassium carbonate. After standing overnight the resultant
solid product 7a–e was filtered, washed with cold water, and crystal-
lized from N,N-dimethylformamide.
5-[3-(Phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-
6-yl]-2-[(3-(phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thia-
diazol-6-yl)methyl]isoindoline-1,3-dione (7a) Yield 73%; mp
Acknowledgments
1
247°C (dec); IR: ν 3041, 2893, 1782, 1726, 1599, 1261 cm-1; H
NMR: δ 7.26–7.34 (m, 5H), 7.13–7.17 (m, 3H), 7.01–7.04 (m, 5H),
5.62 (s, 2H), 5.46 (s, 2H), 5.25 (s, 2H); 13C NMR: δ 169.2, 166.4,
166.2, 166.0, 158.1, 158.0, 155.3, 154.6, 144.4, 144.1, 134.8, 134.4,
134.0, 132.5, 130.1, 129.9, 125.1, 122.2, 122.1, 115.5, 115.3, 59.6,
39.1. Anal. Calcd for C29H19N9O4S2: C, 56.03; H, 3.08; N, 20.28;
S, 10.32. Found: C, 55.89; H, 3.02; N, 20.15; S, 10.13.
We are thankful to North Tehran Branch, Islamic Azad University for
their financial support.
References
Czarnocka, J. A.; Foks, H.; Nasal, A.; Petrusewicz, J.; Damasiewicz,
B.; Radwanska, A.; Kaliszan, R. Synthesis and pharmacological
activity of 5-substituted-s-triazole-3-thiols. Pharmazie 1991, 46,
109–112.
Dong, H. -S.; Wang, B. Synthesis of some novel 3,6-bis(1,2,3-
triazolyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole derivatives. J. Chin.
Chem. Soc. 2005, 52, 103–108.
El-Khawass, S. M.; Habib, N. S.; Fu, H. Synthesis of 1,2,4-triazole,
1,2,4-triazolo[3,4-b][1,3,4]thiadiazole and 1,2,4-triazolo[3,4-b]
[1,3,4]thiadiazine derivatives of benzotriazole. J. Heterocycl.
Chem. 1989, 26, 177–181.
Faghihi, Kh. Facile and rapid synthesis of some optically active
imide-acid derivatives using microwave irradiation. J. Sci. I.A.U
(JSIAU) 2007, 17, 2–6.
5-[3-(Phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-
6-yl]-2-[1-(3-(phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]-
thiadiazol-6-yl)ethyl]isoindoline-1,3-dione (7b) Yield 85%;
mp 185–186°C; [α]2D2 =-20° (c=0.02, DMSO); IR: ν 3050, 2882,
1776, 1722, 1599, 1238, 1080 cm-1; 1H NMR δ 7.25–7.34 (m, 5H),
7.13–7.16 (m, 3H), 6.95–7.06 (m, 5H), 5.91 (q, 1H, J=7.0 Hz), 5.61
(s, 2H), 5.50 (s, 2H), 1.90 (d, 3H J=6.9 Hz); 13C NMR: δ 170.6,
166.4, 166.2, 165.8, 158.0, 157.9, 155.2, 154.6, 144.5, 144.1, 134,8,
134.5, 134.0, 132.8, 130.0, 129.9, 125.1, 122.1, 122.0, 115.4, 115.3,
59.6, 47.1, 17.0. Anal. Calcd for C30H21N9O4S2: C, 56.68; H, 3.33;
N, 19.83; S, 10.09. Found: C, 56.53; H, 3.26; N, 19.70; S, 9.92.
5-[3-(Phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-
6-yl]-2-[1-(3-(phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thi-
adiazol-6-yl)-2-phenylethyl]isoindoline-1,3-dione (7c) Yield
88%; mp 190–193°C; [α]2D2 =-44° (c=0.02, DMSO); IR: ν 3065,
2920, 1778, 1724, 1599, 1238 cm-1; 1H NMR: δ 7.15–7.21 (m, 5H),
7.25–7.36 (m, 8H), 6.96–7.01 (m, 5H), 6.01 (dd, 1H, J=8.9 and 6.8
Hz), 5.60 (s, 2H), 5.50 (s, 2H), 3.71–3.74 (m, 2H); 13C NMR: δ
168.8, 166.4, 166.2, 165.8, 158.1, 158.0, 155.2, 154.8, 144.5, 144.1,
136.0, 135.1, 134.4, 133.7, 132.1, 130.1, 130.0, 129.4, 129.0, 127.7,
125.3, 122.3, 122.1, 115.4, 115.1, 59.6, 52.6, 36.1. Anal. Calcd for
C36H25N9O4S2: C, 60.75; H, 3.54; N, 17.71; S, 9.01. Found: C, 60.52;
H, 3.43; N, 17.51; S, 8.82.
Faghihi, Kh.; Hajibeygi, M. New flame retardant and optically active
poly (amide-imide)s based on N-trimellitylimido-L-amino acid
and phosphine oxide moiety in the main chain: synthesis and
characterization. Mater. Sci. Poland 2010, 28, 545–556.
Faghihi, Kh.; Moghanian, H. Synthesis and charactrization of optically
active poly(amide-imide)s containing phosphosensitive chalcone
units in the main chain. Chin. J. Polymer Sci. 2010, 28, 695–704.
Farghaly, A. -A. H. Synthesis, reactions and antimicrobial activity of
some new indolyl-1,3,4-oxadiazole, triazole and pyrazole deriva-
tives. J. Chin. Chem. Soc. 2004, 51, 147–151.
Farghaly, A. -R.; De Clercq, E. D.; El-Kashef, H. Synthesis and anti-
viral activity of novel[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles,
[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b]-
[1,3,4] thiadiazepines. Arkivoc 2006, 10, 137–151.
Foroughifar, N.; Mobinikhaledi, A.; Ebrahimi, S. Synthesis of a
novel class of Aza crown macrocycles and lariat crown ethers
containing two 1,2,4-triazole rings as subunits. Synthesis 2009a,
15, 2557–2560.
2-[2-Methyl-1-(3-(phenoxymethyl)-[1,2,4]triazolo[3,4-b]-
[1,3,4]thiadiazol-6-yl)propyl]-5-[3-(phenoxymethyl)-[1,2,4]-
triazolo[3,4-b][1,3,4]thiadiazol-6-yl]isoindoline-1,3-dione
(7d) Yield 91%; mp 166–168°C; [α]2D2 =-34° (c=0.02, DMSO);
IR: ν 3040, 2968, 1776, 1720, 1599, 1238, 1078 cm-1; 1H NMR:
δ 7.28–7.36 (m, 5H), 7.13–7.16 (m, 3H), 6.98–7.10 (m, 5H), 5.61
(s, 2H), 5.50 (s, 2H), 5.29 (d, 1H, J=11.3 Hz), 2.91 (m, 1H), 1.02
(d, 3H, J=6.1 Hz), 0.97 (d, 3H, J=5.7 Hz); 13C NMR: δ 167.8, 166.8,
122.1, 166.7, 166.0, 158.1, 158.0, 155.8, 154.7, 144.5, 144.0, 134.9,
134.2, 134.0, 132.6, 130.1, 129.9, 125.3, 122.3, 115.4, 115.3, 59.5,
Foroughifar, N.; Mobinikhaledi, A.; Ebrahimi, S.; Moghanian, H.;
Bodaghi Fard, M. A.; Kalhor, M. Synthesis of a new class of
azathia crown macrocycles containing two 1,2,4-triazole or two
1,3,4-thiadiazole rings as subunits. Tetrahedron Lett. 2009b, 50,
836–839.
Brought to you by | University of Virginia
Authenticated | 134.99.128.41
Download Date | 3/16/13 7:59 PM