A simple and efficient procedure for synthesis of optically active 1,2-bis(s -triazolo (Bis (S-triazolo[3,4- b ][1,3,4]thiadiazole-3-yl) alkane derivatives containing L-amino acid moieties

Article abstract of DOI:10.1080/17415993.2011.628992

A series of 1,2-bis(s-triazolo (Bis (S-triazolo[3,4-b][1,3,4]thiadiazolo-3- yl)alkanes 3a-3k were prepared by condensation reaction of 1,2-bis(4-amino-5- mercapto-S-triazol-3-yl)alkanes 1a-1c with N-phetaloyl-l-amino acids 2a-2d in the presence of the phosphoroxy chloride (POCl₃) as an anhydrous reagent.

Full text of DOI:10.1080/17415993.2011.628992

Journal of Sulfur Chemistry
Vol. 32, No. 6, December 2011, 593–598
A simple and efficient procedure for synthesis of optically active
1,2-bis(s-triazolo (Bis (S-triazolo[3,4-b][1,3,4]thiadiazole-3-yl)
alkane derivatives containing L-amino acid moieties
Naesr Foroughifara,b*, Akbar Mobinikhaledia, Sattar Ebrahimic, Maryam Kamalia
and Maryam Kazemib
b
aDepartment of Chemistry, Arak University, Arak 38156-879, Iran; Faculty of Chemistry, North Tehran
Branch, Islamic Azad University, Tehran, Iran; cDepartment of Chemistry, Malayer Branch, Islamic Azad
University, Malayer, Iran
(Received 9 August 2011; final version received 20 September 2011)
A series of 1,2-bis(s-triazolo (Bis (S-triazolo[3,4-b][1,3,4]thiadiazolo-3-yl)alkanes 3a–3k were prepared
by condensation reaction of 1,2-bis(4-amino-5-mercapto-S-triazol-3-yl)alkanes 1a–1c with N-phetaloyl-
l-amino acids 2a–2d in the presence of the phosphoroxy chloride (POCl3) as an anhydrous reagent.
O
N N
N N
COOH
Y
HS
SH
N
N
NH
N
NH
R
2
2
O
2a–d
1a–c
POCl
N
3
N
N
N
N
O
O
S
S
Y
N
N
N
N
N
O
O
R
R
3a–k
Keywords: N-phetaloyl-l-amino acid; triazole; triazolothiadiazole; phosphoroxy chloride; optically
active
1. Introduction
Bisheterocyclics are interesting compounds because of their various biological activities (1, 2). It
is well documented that heterocycles bearing a triazole or 1,3,4-thiadiazole moiety exhibit many
biological properties such as antiinflammatory (3), antinociceptive (4) and antitumor (5) activity.
*Corresponding author. Email: n_forougifar@yahoo.com
ISSN 1741-5993 print/ISSN 1741-6000 online
© 2011 Taylor & Francis
http://dx.doi.org/10.1080/17415993.2011.628992
http://www.tandfonline.com

594 N. Foroughifar et al.
Additionally, N-bridged heterocyclic compounds derived from 1,2,4-triazoles have found several
applications in the field of medicine, agriculture and industry (6). 1,3,4-Thiadiazoles display a
− −
wide range of biological activities, possibly due to the presence of the toxophoric N C S linkage
(7).Theyarealsoknowntohaveapplicationssuchasantibacterial, antitumorandantiinflammatory
agents, pesticides, herbicides, dyes, lubricants and analytical reagents (8). [1,2,4]-Triazolo-[3,4-
b]-[1,3,4]-thiadiazole derivatives, produced by fusion of the biolibale [1,2,4]-triazole and [1,3,4]-
thiadiazole rings, are reported to possess pharmacological activities (9). Preparation of these
compounds has extensively been studied during the past few years, and the most convenient
and general method for the synthesis of [1,2,4]-triazolo-[3,4-b]-[1,3,4]-thiadiazole derivatives
involves the reaction of 5-substituted 4-amino-(4H)-1,2,4-triazole-3-thioles with carboxylic acids
(10–12). Nevertheless, to the best of our knowledge, there is no report for preparation of optically
active bis-1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole ring systems containing l-amino acids.
On the basis of these reports and also in continuation of our research program on the synthesis
of heterocyclic compounds containing 1,2,4-triazole and optically active compounds (13–18), we
wish to report the synthesis of some new 3,6-disubstituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles
containing l-amino acid moiety, with the hope to improve their biological activities, because chi-
rality is an important factor of the bioactive molecules and a recognition phenomenon associated
with these molecules.
2. Results and discussion
This paper describes a facile one-step synthesis of bis-triazolothiadiazole derivatives 3 via reaction
between1 molofbis-aminotriazolewith2 molofaliphaticacid. N-phthaloyl-l-aminoacids2a–2d
were synthesized according to the procedure described in literature (19). The starting 1,2-bis(4-
amino-5-mercapto-4H-1,2,4-triazol-3-yl)alkanes (1a–1c) were prepared by heating an aliphatic
diacid with 2 equiv. of carbonothioic dihydrazide in an oil bath at 170◦C (20). The resultant
bis-5,5ꢀ-(alkane-1,2-diyl)bis(4-amino-4H-1,2,4-triazole-3-thiol) compounds 1a–1c were further
converted to 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazoles 3a–3j through a one-pot reaction by conden-
sation with N-phthaloyl-l-amino acids 2a–2d in the presence of phosphoroxy chloride (POCl3)
as outlined in Scheme 1.
O
N
N
N
N
R = H 2a
R = CH3 2b
R = PhCH2 2c
R = Isopropyl, 2d
R = Isobutyl, 2e
COOH
Y
HS
SH
N
N
N
R
NH2
NH2
Y= (CH2)2 1a
Y= (CH2)3 1b
Y= (CH2)4 1c
O
2a–d
1a–c
R = H, Y = (CH2)2 3a
R = H, Y = (CH2)4 3b
POCl3
N
R = CH3, Y = (CH2)2 3c
R = CH3, Y = (CH2)3 3d
R = CH3, Y = (CH2)4 3e
R = Isopropyl, Y = (CH2)2 3f
R = Isopropyl, Y = (CH2)3 3g
R = Isopropyl, Y = (CH2)4 3h
R = PhCH2, Y = (CH2)2 3i
R = PhCH2, Y = (CH2)3 3j
R = PhCH2, Y = (CH2)4 3k
N
N
N
N
N
O
O
S
S
Y
N
N
N
N
O
O
R
R
3a–k
Scheme 1. Synthesis of compounds 3a–3k.
Phosphorus oxychloride was necessary for this condensation, which activates the carboxyl
group of amino acids and increases its electrophilicity. This procedure afforded various

Journal of Sulfur Chemistry 595
triazolothiadiazoles in 52–80% yields. All compounds were structurally characterized by using
IR, 1H NMR and 13C NMR data. The IR spectra of the bis(4-amino-5-mercapto-4H-1,2,4-triazol-
3-yl)alkanes (1a–1c) showed absorption bands at 3161 and 3286 cm−1 due to the NH2 groups,
which were absent in the IR spectra of the aza crown compounds 3a–3k. Similarly, the 1H NMR
spectra of the bistriazoles 1a–1c showed a broad signal at δ = 5.56 ppm attributed to the reso-
nance of NH2 groups, which was not present in the spectra of compounds 3a–3k. In addition, the
substituted bis(4-amino-4H-1,2,4-triazole-3-thiol) derivatives showed a peak around 13.8 ppm
indicating the existence of the thiol group, which clearly disappeared in the title compounds
confirms their condensed structure.
3. Conclusion
We have been able to synthesize some N-phetaloyl-l-amino acids having a free terminal carboxyl
function, which can react with bis-amino triazole. This reaction may be useful for combinational
synthesis of type 3 compounds having various R and Y substitutions with a view to test for
biological activities.
4. Experimental
4.1. General
Melting points were determined using an electrothermal digital apparatus and are corrected. Purity
of the compound was checked by thin-layer chromatography using EtOH/n-hexane (1:1, v/v)
as an eluent. IR spectra were prepared on a galaxy series FT-IR 5000 spectrophotometer using
KBr discs. NMR spectra were recorded on a Bruker spectrophotometer (300 MHz) in DMSO-d6
using TMS as an internal standard. Specific rotations were measured by using a Perkin Elmer 341
polarimeter.
4.2. General procedure for preparation of compounds 3a–3k
A mixture of 1,2-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)alkanes (1a–1c) (1 mmol) and
corresponding N-phthaloyl-l-amino acids 2a–2d (2 mmol) in POCl3 (7 ml) was refluxed for 16 h.
The reaction mixture was slowly poured onto crushed ice with stirring and neutralized with solid
potassium bicarbonate. The mixture was allowed to stand overnight and the obtained solid was
filtered and washed with cold water. The compound so obtained was dried and crystallized from
ethanol to give the pure products 3a–3k.
4.3. 2,2ꢀ-(3,3ꢀ-(Ethane-1,2-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(methylene)diisoindoline-1,3-dione (3a)
Yield: 52%; m.p. 294–296◦C; IR (KBr) (ν, cm−1): 3043 (aromatic CH stretch), 2933 (aliphatic
1
=
=
=
CH stretch), 1770, 1712 (C O), 1600 (C N), 1518, 1467 (C C); H NMR (DMSO-d6, δ, ppm):
7.94 (d, 4H, J = 5.1 Hz, Harom.), 7.89 (d, 4H, J = 5.0 Hz, Harom.), 5.13 (s, 4H, 2× N-CH2), 3.49
(s, 4H, 2× CH2); 13C NMR (DMSO-d6, δ, ppm): 22.0, 38.0, 124.0, 131.8, 135.4, 146.1, 153.9,
165.5, 167.5. Anal. Calcd. for C26H16N10O4S2: C, 52.34; H, 2.70, N, 23.48%. Found: C, 52.51;
H, 2.55, N, 23.31%.

596 N. Foroughifar et al.
4.4. 2,2ꢀ-(3,3ꢀ-(Butane-1,4-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(methylene)diisoindoline-1,3-dione (3b)
Yield: 52%; m.p. 282–284◦C; IR (KBr): 3032 (aromatic CH stretch), 2928 (aliphatic CH stretch),
1772, 1720 (C O), 1521, 1469 (C C) cm−1; 1H NMR (DMSO-d6, δ, ppm): 7.88 (s, 8H, Harom.),
5.81 (s, 4H, 2× N-CH2), 2.95 (br, 4H, 2× CH2), 1.77 (br, 4H, 2× CH2); 13C NMR (DMSO-
d6, δ, ppm): 24.1, 25.6, 38.0, 124.0, 131.6, 135.3, 147.5, 153.4, 165.0, 167.4. Anal. Calcd. for
C28H20N10O4S2: C, 53.84; H, 3.23, N, 22.42%. Found: C, 53.71; H, 3.37, N, 22.65%.
=
=
4.5. 2,2ꢀ-(1,1ꢀ-(3,3ꢀ-(Ethane-1,2-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(ethane-1,1-diyl))diisoindoline-1,3-dione (3c)
22
Yield: 70%; m.p. 290–293◦C; [α]D = −40 (c = 0.01, DMSO); IR (KBr) (ν, cm−1): 3040 (aro-
1
=
=
matic CH stretch), 1774, 1710 (C O), 1518, 1467 (C C); H NMR (DMSO-d6, δ, ppm): 7.90
(s, 8H, Harom.), 5.80 (s, 2H, 2× N-CH), 3.52 (s, 4H, 2× CH2), 1.85 (br, 6H, 2× CH3); 13C NMR
(DMSO-d6, δ, ppm): 17.0, 22.1, 46.7, 124.0, 131.7, 135.4, 146.2, 154.0, 167.3, 170.0.Anal. Calcd.
for C28H20N10O4S2: C, 53.84; H, 3.23, N, 22.42%. Found: C, 53.98; H, 3.30, N, 22.53%.
4.6. 2,2ꢀ-(1,1ꢀ-(3,3ꢀ-(Propane-1,3-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(ethane-1,1-diyl))diisoindoline-1,3-dione (3d)
22
Yield: 83%; m.p. 243–246◦C; [α]D = −10 (c = 0.01, DMSO); IR (KBr) (ν, cm−1): 3030 (aro-
1
=
=
matic CH stretch), 2941 (aliphatic CH stretch), 1778, 1714 (C O), 1608 (C N); H NMR
(DMSO-d6, δ, ppm): 8.00 (s, 8H, Harom.), 5.82 (q, 2H, J = 7.1 Hz, 2× N-CH), 3.13 (br, 4H, 2×
CH2), 2.29 (br, 2H, CH2), 1.87 (br, 6H, 2× CH3); 13C NMR (DMSO-d6, δ, ppm): 16.7, 23.2,
24.0, 46.8, 123.8, 131.6, 135.4, 147.2, 153.5, 167.3, 169.7. Anal. Calcd. for C29H22N10O4S2: C,
54.54; H, 3.47, N, 21.93%. Found: C, 54.38; H, 3.51, N, 22.14%.
4.7. 2,2ꢀ-(1,1ꢀ-(3,3ꢀ-(Butane-1,4-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(ethane-1,1-diyl))diisoindoline-1,3-dione (3e)
22
Yield: 70%; m.p. 243–245◦C; [α]D = −10 (c = 0.01, DMSO); IR (KBr) (ν, cm−1): 3041 (aro-
=
=
matic CH stretch), 2964, 2874 (aliphatic CH stretch), 1780, 1720 (C O), 1610 (C N), 1516,
1467 (C C) cm−1; 1H NMR (DMSO-d6, δ, ppm): 7.88 (s, 8H, Harom.), 5.81 (br, 2× N-CH), 3.00
=
(br, 4H, 2× CH2), 1.77–1.85 (m, 10H, 2× CH3, 2× CH2); 13C NMR (DMSO-d6, δ, ppm): 17.0,
24.1, 25.6, 46.8, 124.0, 131.7, 135.4, 147.5, 153.4, 167.3, 169.7.Anal. Calcd. for C30H24N10O4S2:
C, 55.20; H, 3.71, N, 21.46%. Found: C, 55.43; H, 3.79, N, 21.31%.
4.8. 2,2ꢀ-(1,1ꢀ-(3,3ꢀ-(Ethane-1,2-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(2-methyl propane-1,1-diyl))diisoindoline-1,3-dione (3f)
22
Yield: 80%; m.p. 243–245◦C; [α]D = −40 (c = 0.01, DMSO); IR (KBr): 3035 (aromatic CH
−
−
−
stretch), 2968, 2876 (aliphatic CH stretch), 1782, 1716 (C O), 1612 (C N), 1518, 1469 (C C)
cm−1; 1H NMR (DMSO-d6, δ, ppm): 7.90 (s, 8H, Harom.), 5.13 (d, 2H, J = 10.1 Hz, 2× N-CH),
3.53 (s, 4H, 2× CH2), 2.90 (br, 2H, 2× CH), 0.98 (d, 6H, J = 6.3 Hz, 2× CH3), 0.90 (d, 6H,
J = 6.2 Hz, 2× CH3); 13C NMR (DMSO-d6, δ, ppm): 19.4, 20.0, 22.3, 29.6, 57.9, 124.1, 131.2,
135.5, 146.1, 154.2, 166.9, 167.7.Anal. Calcd. for C32H28N10O4S2: C, 56.46; H, 4.15, N, 20.58%.
Found: C, 56.28; H, 4.01, N, 20.75%.

Journal of Sulfur Chemistry 597
4.9. 2,2ꢀ-(1,1ꢀ-(3,3ꢀ-(Propane-1,3-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(2-methyl propane-1,1-diyl))diisoindoline-1,3-dione (3g)
22
Yield: 76%; m.p. 226–228◦C; [α]D = −80 (c = 0.01, DMSO); IR (KBr) cm−1: 3050 (aromatic
−
=
CH stretch), 2966, 2874 (aliphatic CH stretch), 1782, 1718 (C O), 1612 (C N), 1518, 1469
1
=
(C C); H NMR (DMSO-d6, δ, ppm): 7.90 (s, 8H, Harom.), 5.22 (d, 2H, J = 9.9 Hz, 2× N-CH),
3.15 (br, 4H, 2× CH2), 2.93 (br, 2H, 2× CH), 2.29 (br, 2H, CH2), 1.01 (br, 6H, 2× CH3), 0.93
(br, 6H, 2× CH3); 13C NMR (DMSO-d6, δ, ppm): 19.4, 20.0, 23.4, 24.0, 29.5, 57.9, 124.1, 131.2,
135.5, 147.1, 154.0, 166.8, 167.7.Anal. Calcd. for C33H30N10O4S2: C, 57.05; H, 4.35, N, 20.16%.
Found: C, 57.20; H, 4.30, N, 20.27%.
4.10. 2,2ꢀ-(1,1ꢀ-(3,3ꢀ-(Butane-1,4-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(2-methyl propane-1,1-diyl))diisoindoline-1,3-dione (3h)
22
Yield: 85%; m.p. 226–228◦C; [α]D = −80 (c = 0.01, DMSO); IR (KBr): 3036 (aromatic CH
−1
=
=
=
stretch), 2928 (aliphatic CH stretch), 1776, 1712 (C O), 1610 (C N), 1518, 1462 (C C) cm
;
1H NMR (DMSO-d6, δ, ppm): 7.88 (s, 8H, Harom.), 5.18 (br, 2H, 2× N-CH), 2.89–3.02 (m, 6H,
2× CH2, 2× CH), 1.84 (br, 4H, 2× CH2), 0.97 (br, 6H, 2× CH3), 0.90 (br, 6H, 2× CH3); 13
C
NMR (DMSO-d6, δ, ppm): 19.4, 20.0, 24.2, 25.7, 29.5, 57.9, 124.0, 131.2, 135.5, 147.4, 153.9,
166.7, 167.7. Anal. Calcd. for C34H32N10O4S2: C, 57.61; H, 4.55, N, 19.76%. Found: C, 57.50;
H, 4.49, N, 19.56%.
4.11. 2,2ꢀ-(1,1ꢀ-(3,3ꢀ-(Ethane-1,2-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(2-phenyl ethane-1,1-diyl))diisoindoline-1,3-dione (3i)
22
Yield: 80%; m.p. 238–240◦C; [α]D = −40 (c = 0.01, DMSO); IR (KBr): 3030 (aromatic CH
−1
=
=
=
stretch), 2930 (aliphatic CH stretch), 1778, 1718 (C O), 1612 (C N), 1520, 1469 (C C) cm
;
1H NMR (DMSO-d6, δ, ppm): 7.88 (s, 8H, Harom.), 7.20 (br, 10H, Harom.), 5.98–6.00 (m, 2H, 2×
N-CH), 3.58–3.68 (m, 4H, 2× PhCH2), 3.55 (s, 4H, 2× CH2); 13C NMR (DMSO-d6, δ, ppm):
22.2, 36.0, 52.3, 124.1, 127.6, 128.9, 129.3, 130.9, 135.6, 136.0, 146.3, 153.7, 167.3, 168.3. Anal.
Calcd. for C40H28N10O4S2: C, 61.84; H, 3.63, N, 18.03%. Found: C, 61.71; H, 3.75, N, 18.11%.
4.12. 2,2ꢀ-(1,1ꢀ-(3,3ꢀ-(Propane-1,3-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(2-phenyl ethane-1,1-diyl))diisoindoline-1,3-dione (3j)
22
Yield: 85%; m.p. 235–237◦C; [α]D = −10 (c = 0.01, DMSO); IR (KBr): 3035 (aromatic CH
stretch), 2930 (aliphatic CH stretch), 1776, 1714 (C O), 1605 (C N) cm−1; 1H NMR (DMSO-
d6, δ, ppm): 7.82 (s, 8H, Harom.), 7.13–7.18 (m, 10H, Harom.), 6.04–6.15 (m, 2H, 2× N-CH),
3.97–4.15 (m, 4H, 2× PhCH2), 3.12 (br, 4H, 2× CH2), 2.30 (br, 2H, CH2); 13C NMR (DMSO-d6,
δ, ppm) 23.2, 23.9, 36.0, 52.3, 124.1, 127.6, 128.9, 129.4, 130.8, 135.6, 136.0, 147.2, 153.6,
167.4, 168.1. Anal. Calcd. for C41H30N10O4S2: C, 62.27; H, 3.82, N, 17.71%. Found: C, 62.13;
H, 3.89, N, 17.53%.
=
=
4.13. 2,2ꢀ-(1,1ꢀ-(3,3ꢀ-(Butane-1,4-diyl)bis([1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6,3-
diyl))bis(2-phenyl ethane-1,1-diyl))diisoindoline-1,3-dione (3k)
22
Yield: 85%; m.p. 232–234◦C; [α]D = −80 (c = 0.01, DMSO); IR (KBr): 3050 (aromatic CH
stretch), 2942 (aliphatic CH stretch), 1776, 1712 (C O), 1610 (C N) cm−1; 1H NMR (DMSO-
d6, δ, ppm): 7.84 (s, 8H, Harom.), 7.21 (br, 10H, Harom.), 6.01 (br, 2H, 2× N-CH), 3.68 (br, 4H,
=
=

598 N. Foroughifar et al.
2× PhCH2), 3.01 (br, 4H, 2× CH2), 1.80 (br, 4H, 2× CH2); 13C NMR (DMSO-d6, δ, ppm) 24.1,
25.7, 36.1, 52.4, 124.0, 127.6, 128.9, 129.4, 130.9, 135.5, 136.1, 147.5, 153.5, 167.3, 167.9. Anal.
Calcd. for C42H32N10O4S2: C, 62.67; H, 4.01, N, 17.40%. Found: C, 62.85; H, 3.96, N, 17.56%.
Acknowledgement
We gratefully acknowledge the financial support from the Research Council of Arak University.
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