Synthesis of 2-(5-(2-chlorophenyl)2-furoylamido)-5-aryloxymethyl-1,3,4-thiadiazoles under microwave irradiation

Article abstract of DOI:10.1081/SCC-100104332

2-(5-(2-chlorophenyl)-2-furoylamido)-5-aryloxymethyl-1,3,4-thiadiazoles (IIa-j) are synthesized under microwave irradiation via the cyclization of 1-aryloxyacetyl-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicarbazides (Ia-j) in the presence of glacial acetic

Full text of DOI:10.1081/SCC-100104332

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SYNTHESIS OF 2-(5-(2-CHLOROPHENYL)-2-
FUROYLAMIDO)-5-ARYLOXYMETHYL-1,3,4-
THIADIAZOLES UNDER MICROWAVE IRRADIATION
Zheng Li a , Xicun Wang b & Yuxia Da a
a Department of Chemistry , Northwest Normal University , Lanzhou, Gansu, 730070, P.R.
China
b Department of Chemistry , Northwest Normal University , Lanzhou, Gansu, 730070, P.R.
China
Published online: 16 Aug 2006.
To cite this article: Zheng Li , Xicun Wang & Yuxia Da (2001) SYNTHESIS OF 2-(5-(2-CHLOROPHENYL)-2-FUROYLAMIDO)-5-
ARYLOXYMETHYL-1,3,4-THIADIAZOLES UNDER MICROWAVE IRRADIATION, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 31:12, 1829-1836, DOI: 10.1081/SCC-100104332
To link to this article: http://dx.doi.org/10.1081/SCC-100104332
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SYNTHETIC COMMUNICATIONS, 31(12), 1829–1836 (2001)
SYNTHESIS OF 2-(5-(2-CHLOROPHENYL)-
2-FUROYLAMIDO)-5-ARYLOXYMETHYL-
1,3,4-THIADIAZOLES UNDER MICROWAVE
IRRADIATION
Zheng Li, Xicun Wang,* and Yuxia Da
Department of Chemistry, Northwest Normal University,
Lanzhou, Gansu, 730070, P.R. China
ABSTRACT
2-(5-(2-chlorophenyl)-2-furoylamido)-5-aryloxymethyl-1,3,4-
thiadiazoles (IIa–j) are synthesized under microwave
irradiation via the cyclization of 1-aryloxyacetyl-4-(5-
(2-chlorophenyl)-2-furoyl)-thiosemicarbazides (Ia–j) in the
presence of glacial acetic acid.
5-Aryl-2-furoic acid derivatives have been used as antibacterial agent,1
local anesthesia,2 analgesic3 and plant-growth regulator.4–5 Meanwhile, sub-
stituted 1,3,4-thiadiazoles have also attracted much attention due to their
diverse biological activities, such as antimicrobial,6–11 antibacterial,12 anes-
thetic,13 antithrombotic,14 anticonvulsant,15 cardiotonic,16 antihyperten-
sive,17 antiinflammatory18 and antiulcer19 activity.
Keeping in view the above facts, we report herein the preparation of a
new series of compounds bearing both 1,3,4-thiadiazole and 5-aryl-2-furoyl
moiety, with the objective of obtaining new biologically active compounds.
* Corresponding author.
1829
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

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LI, WANG, AND DA
Although the substituted 1,3,4-thiadiazoles can be prepared from the
substituted thiosemicarbazides by conventional method,20,21 the reaction
yield is often not high and the reaction time is always very long. This
paper we introduce a convenient and efficient microwave method.
Reaction of 5-(2-chlorophenyl)-2-furoyl chloride with ammonium
thiocyanate catalyzed by polyethylene glycol-400 (PEG-400) at room tempe-
rature gives 5-(2-chlorophenyl)-2-furoylisothiocyanate, which on treatment
with aryloxyacetic acid hydrazides in situ at room temperature affords
1-aryloxyacetyl-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicarbazides (Iaꢀj) in
excellent yields. Compounds (Iaꢀj) on exposure to microwave irradiation in
the presence of glacial acetic acid result in the formation of 2-(5-(2-chloro-
phenyl)-2-furoylamido)-5-aryloxymethyl-1,3,4-thiadiazoles (IIa–j) (Scheme).
Scheme.
The characterization of compounds Iaꢀj and IIaꢀj is based on their IR
(KBr), 1H NMRand elemental analyses. The IRspectra exhibit a character-
istic strong absorption at 1169–1210 cmꢀ1 for compounds Iaꢀj attributable
to the C¼S of the thio residue. The carbonyl absorption is observed at 1656–
1
1705 cmꢀ1 for Iaꢀj and 1659–1676 cmꢀ1 for IIaꢀj. The H NMRspectral
data of Ia–j in d6-dimethylsulfoxide show peaks at 12.42–12.62 (NHa), 11.84–
11.91 (NHb), 11.01–11.21 (NHc) and 4.63–4.91 ppm (CH2). In contrast, the
1H NMRspectral data of IIa–j in the same deuterated solvent show signals at
13.17–13.45 (NH), indicating a significant downfield shift (ca. 0.8 ppm) com-
pared to the corresponding NHa of Ia–j, and singlet at 5.40–5.56 (CH2). All
found of C, H, N of Ia–j and IIa–j are good agreement with the calculated.
EXPERIMENTAL
IRspectra were recorded using KBr pellets on an Alpha Centauri
FTIRspectrophotometer and 1H NMRspectra on a FT-80A instrument

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1,3,4-THIADIAZOLES
1831
using (CD3)2SO as solvent and Me4Si as internal standard. Elemental ana-
lyses were performed on a Carlo-Erba 1106 Elemental Analysis instrument.
Melting points were observed in an open capillary tube and uncorrected.
5-(2-chlorophenyl)-2-furoylchloride22 and aryloxyacetic acid hydrazides23
were prepared according to literature procedures. Ammonium thiocyanate,
glacial acetic acid and PEG-400 were commercially available and used as
received.
General Procedure for Preparation of Ia–j
A
suspension of 5-(2-chlorophenyl)-2-furoyl chloride (0.36 g,
1.5 mmol), ammonium thiocyanate (0.20 g, 2.6 mmol) and PEG-400
(0.02 g, 0.05 mmol) in 40 mL of methylene chloride was stirred for 1 h at
room temperature, then aryloxyacetic acid hydrazide (1.45 mmol) was
added. The mixture was stirred for another 0.5 h, and a precipitate was
formed. The resulting mixture was filtered and washed with water to
remove inorganic salts. The residue was recrystallized from DMF-EtOH-
H2O to yield I as crystals. The physical and spectral results are shown below.
1-phenyloxyacetyl-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicarbazide
(Ia): white solid. yield: 83%. m.p.: 195–196ꢁC. 1H NMR(80 MHz, DMSO-
d6) d 12.44 (1H, s, NH), 11.89 (1H, s, NH), 11.14 (1H, s, NH), 7.34–8.26
(11H, m, Ar-H and Fu-H), 4.91 (2H, s, CH2). IR(KBr, g cmꢀ1): 3276, 3151
(N-H), 1701, 1669 (C¼O), 1210 (C¼S). Anal. Calcd. for C20H16N3O4SCl: C,
55.88; H, 3.75; N, 9.77. Found: C, 56.01; H, 3.61; N, 9.89.
1-(2-tolyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicarbazide
(Ib): white solid. yield: 82%. m.p.: 209–210ꢁC. 1H NMR(80 MHz, DMSO-
d6) d 12.42 (1H, s, NH), 11.85 (1H, s, NH), 11.08 (1H, s, NH), 6.86–8.53
(10H, m, Ar-H and Fu-H), 4.63 (2H, s, CH2), 2.30 (3H, s, CH3). IR(KBr,
g cmꢀ1): 3308, 3226, 3119 (N-H), 1698, 1658 (C¼O), 1197 (C¼S). Anal.
Calcd. for C21H18N3O4SCl: C, 56.82; H, 4.09; N, 9.47. Found: C, 56.96;
H, 4.01; N, 9.23.
1-(4-tolyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicarbazide
(Ic): white solid. yield: 81%. m.p.: 187–188ꢁC. H NMR(80 MHz, DMSO-
1
d6) d 12.51 (1H, s, NH), 11.87 (1H, s, NH), 11.01 (1H, s, NH), 6.94–8.60
(10H, m, Ar-H and Fu-H), 4.65 (2H, s, CH2), 2.26 (3H, s, CH3). IR(KBr,
g cmꢀ1): 3281, 3213, 3124 (N-H), 1696, 1664 (C¼O), 1172 (C¼S). Anal.
Calcd. for C21H18N3O4SCl: C, 56.82; H, 4.09; N, 9.47. Found: C, 57.03;
H, 3.98; N, 9.54.
1-(4-methoxylphenyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicar-
bazide(Id) : White solid. yield: 85%. m.p.: 189–190ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 12.54 (1H, s, NH), 11.89 (1H, s, NH), 11.08 (1H, s, NH), 7.01–

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LI, WANG, AND DA
8.57 (10H, m, Ar-H and Fu-H), 4.68 (2H, s, CH2), 3.43 (3H, s, CH3). IR
(KBr, g cmꢀ1): 3351, 3276, 3160 (N-H), 1698, 1656 (C¼O), 1188 (C¼S).
Anal. Calcd. for C21H18N3O5SCl: C, 54.84; H, 3.94; N, 9.14. Found: C,
54.63; H, 4.02; N, 9.28.
1-(1-naphthyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicarba-
zide(I)e : White solid. yield: 83%. m.p.: 210–211ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 12.51 (1H, s, NH), 11.84 (1H, s, NH), 11.21 (1H, s, NH),
7.30–8.27 (13H, m, Ar-H and Fu-H), 4.82 (4H, s, CH2). IR(KBr,
g cmꢀ1): 3350, 3271, 3180 (N-H), 1701, 1663 (C¼O), 1175 (C¼S). Anal.
Calcd. for C24H18N3O4SCl: C, 60.06; H, 3.78; N, 8.76. Found: C, 60.36;
H, 3.82; N, 8.59.
1-(2-naphthyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicarba-
zide(If ) : White solid. yield: 85%. m.p.: 203–204ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 12.49 (1H, s, NH), 11.86 (1H, s, NH), 11.09 (1H, s, NH),
7.21–8.34 (13H, m, Ar-H and Fu-H), 4.81 (4H, s, CH2). IR(KBr,
g cmꢀ1): 3346, 3268, 3180 (N-H), 1698, 1657 (C¼O), 1178 (C¼S). Anal.
Calcd. for C24H18N3O4SCl: C, 60.06; H, 3.78; N, 8.76. Found: C, 60.28;
H, 3.88; N, 8.63.
1-(4-chlorophenyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemi-
carbazide(Ig) : White solid. yield: 89%. m.p.: 205–206ꢁC. 1H NMR(80 MHz,
DMSO-d6) d 12.48 (1H, s, NH), 11.91 (1H, s, NH), 11.12 (1H, s, NH),
6.98–8.12 (10H, m, Ar-H and Fu-H), 4.83 (2H, s, CH2). IR(KBr, g cmꢀ1):
3301, 3227, 3146 (N-H), 1692, 1668 (C¼O), 1170 (C¼S). Anal. Calcd. for
C20H15N3O4SCl2: C, 51.73; H, 3.26; N, 9.05. Found: C, 51.99; H, 3.15;
N, 8.89.
1-(2-nitrophenyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicar-
bazide(Ih) : White solid. yield: 84%. m.p.: 209–210ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 12.62 (1H, s, NH), 11.90 (1H, s, NH), 11.13 (1H, s, NH),
7.21–8.11 (10H, m, Ar-H and Fu-H), 4.87 (2H, s, CH2). IR(KBr, g cmꢀ1):
3270, 3216 (N-H), 1705, 1667 (C¼O), 1169 (C¼S). Anal. Calcd. for
C20H15N4O6SCl: C, 50.59; H, 3.18; N, 11.80. Found: C, 50.86; H, 3.21;
N, 11.70.
1-(3-nitrophenyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicar-
bazide(Ii) : White solid. yield: 81%. m.p.: 211–212ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 12.60 (1H, s, NH), 11.87 (1H, s, NH), 11.11 (1H, s, NH),
7.20–8.11 (10H, m, Ar-H and Fu-H), 4.89 (2H, s, CH2). IR(KBr,
g cmꢀ1): 3286, 3231 (N-H), 1701, 1672 (C¼O), 1172 (C¼S). Anal. Calcd.
for C20H15N4O6SCl: C, 50.59; H, 3.18; N, 11.80. Found: C, 50.76; H, 3.11;
N, 11.67.
1-(4-nitrophenyloxyacetyl)-4-(5-(2-chlorophenyl)-2-furoyl)-thiosemicar-
bazide(Ij) : White solid. yield: 87%. m.p.: 206–207ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 12.61 (1H, s, NH), 11.86 (1H, s, NH), 11.13 (1H, s, NH),

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1833
7.18–8.06 (10H, m, Ar-H and Fu-H), 4.89 (2H, s, CH2). IR(KBr, g cmꢀ1):
3277, 3208, (N-H), 1703, 1666 (C¼O), 1174 (C¼S). Anal. Calcd. for
C20H15N4O6SCl: C, 50.59; H, 3.18; N, 11.80. Found: C, 50.46; H, 3.08;
N, 11.72.
General Procedure for the Preparation of Compounds IIa–j
A mixture of compound I (0.5 mol) and glacial acetic acid (5 mL) was
irradiated in a microwave oven at 375 W for 5 minutes, the completion of
the reaction was monitored by TLC. The excess of glacial acetic acid was
removed by evaporation, the residue was poured into ice (100 g), and the
precipitate was collected by filtration and washed with water (3 ꢂ 20 mL).
The product was obtained as white crystals after recrystallization from
DMF-EtOH-H2O. The physical and spectral date of compounds IIa–j are
shown below.
2-(5-(2-chlorophenyl)-2-furoylamido)-5-phenyloxymethyl-1,3,4-thiadia-
zole(IIa) : White solid. yield: 94%. m.p.: 227–228ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.21 (1H, s, NH), 7.01–8.40 (11H, m, Ar-H and Fu-H), 5.41
(2H, s, CH2). IR(KBr, g cmꢀ1): 3179 (N-H), 1667 (C¼O), 1605, 1507, 1451,
1107 (C¼N-N-C¼S). Anal. Calcd. for C20H14N3O3SCl: C, 58.32; H, 3.43;
N, 10.20. Found: C, 58.51; H, 3.32; N, 10.47.
2-(5-(2-chlorophenyl)-2-furoylamido)-5-(2-tolyloxymethyl)-1,3,4-thia-
diazole(IIb) : White solid. yield: 92%. m.p.: 238–239ꢁC. 1H NMR(80 MHz,
DMSO-d6) d 13.17 (1H, s, NH), 6.97–8.51 (10H, m, Ar-H and Fu-H), 5.44
(2H, s, CH2), 2.26 (3H, s, CH3). IR(KBr, g cmꢀ1): 3186 (N-H), 1670 (C¼O),
1602, 1510, 1446, 1101 (C¼N-N-C¼S). Anal. Calcd. for C21H16N3O3SCl: C,
59.22; H, 3.79; N, 9.87. Found: C, 58.97; H, 3.63; N, 10.03.
2-(5-(2-chlorophenyl)-2-furoylamido)-5-(4-tolyloxymethyl)-1,3,4-thiadia-
zole(IIc) : White solid. yield: 97%. m.p.: 221–222ꢁC. H NMR(80 MHz,
1
DMSO-d6) d 13.36 (1H, s, NH), 6.99–8.53 (10H, m, Ar-H and Fu-H), 5.43
(2H, s, CH2), 2.21 (3H, s, CH3) IR(KBr, g cmꢀ1): 3189 (N-H), 1669 (C¼O),
1600, 1513, 1449, 1099 (C¼N-N-C¼S). Anal. Calcd. for C21H16N3O3SCl:
C, 59.22; H, 3.79; N, 9.87. Found: C, 59.44; H, 3.96; N, 9.69.
2-(5-(2-chlorophenyl)-2-furoylamido)-5-(4-methoxylphenyloxymethyl)-
1,3,4-thiadiazole(IId) : White solid. yield: 96%. m.p.: 233–234ꢁC. H NMR
1
(80 MHz, DMSO-d6) d 13.40 (1H, s, NH), 6.88–8.60 (10H, m, Ar-H
and Fu-H), 5.40 (2H, s, CH2), 3.40 (3H, s, CH3) IR(KBr, g cmꢀ1): 3163
(N-H), 1673 (C¼O), 1608, 1503, 1442, 1105 (C¼N-N-C¼S). Anal. Calcd.
for C21H16N3O4SCl: C, 57.08; H, 3.65; N, 9.51. Found: C, 56.86; H,
3.57; N, 9.70.

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LI, WANG, AND DA
2-(5-(2-chlorophenyl)-2-furoylamido)-5-(1-naphthyloxymethyl)-1,3,4-
thiadiazole(II)e : White solid. yield: 91%. m.p.: 248–249ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.38 (1H, s, NH), 6.93–8.49 (13H, m, Ar-H and
Fu-H), 5.42 (2H, s, CH2). IR(KBr, g cmꢀ1): 3184 (N-H), 1669 (C¼O), 1601,
1515, 1481, 1107 (C¼N-N-C¼S). Anal. Calcd. for C24H16N3O3SCl: C,
62.40; H, 3.49; N, 9.10. Found: C, 62.15; H, 3.28; N, 9.29.
2-(5-(2-chlorophenyl)-2-furoylamido)-5-(2-naphthyloxymethyl)-1,3,4-
thiadiazole(IIf) : White solid. yield: 98%. m.p.: 240–241ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.41 (1H, s, NH), 7.02–8.51 (13H, m, Ar-H
and Fu-H), 5.41 (2H, s, CH2). IR(KBr, g cmꢀ1): 3188 (N-H), 1671
(C¼O), 1603, 1516, 1476, 1104 (C¼N-N-C¼S). Anal. Calcd. for
C24H16N3O3SCl: C, 62.40; H, 3.49; N, 9.10. Found: C, 62.56; H, 3.40;
N, 9.33.
2-(5-(2-chlorophenyl)-2-furoylamido)-5-(4-chlorophenyloxymethyl)-
1,3,4-thiadiazole(IIg) : White solid. yield: 96%. m.p.: 244–245ꢁC. H NMR
1
(80 MHz, DMSO-d6) d 13.45 (1H, s, NH), 6.79–8.61 (10H, m, Ar-H
and Fu-H), 5.46 (2H, s, CH2). IR(KBr, g cmꢀ1): 3190 (N-H), 1676
(C¼O), 1600, 1509, 1457, 1110 (C¼N-N-C¼S). Anal. Calcd. for
C20H13N3O3SCl2: C, 53.82; H, 2.94; N, 9.41. Found: C, 54.02; H, 3.13;
N, 9.26.
2-(5-(2-chlorophenyl)-2-furoylamido)-5-(2-nitrophenyloxymethyl)-1,3,4-
thiadiazole(IIh) : White solid. yield: 97%. m.p.: 245–246ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.26 (1H, s, NH), 7.03–8.52 (10H, m, Ar-H and
Fu-H), 5.51 (2H, s, CH2). IR(KBr, g cmꢀ1): 3220 (N-H), 1676 (C¼O), 1609,
1511, 1483, 1102 (C¼N-N-C¼S). Anal. Calcd. for C20H13N4O5SCl: C,
52.58; H, 2.87; N, 12.26. Found: C, 52.63; H, 2.92; N, 12.40.
2-(5-(2-chlorophenyl)-2-furoylamido)-5-(3-nitrophenyloxymethyl)-1,3,4-
thiadiazole(IIi) : White solid. yield: 96%. m.p.: 274–275ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.37 (1H, s, NH), 7.11–8.46 (10H, m, Ar-H
and Fu-H), 5.48 (2H, s, CH2). IR(KBr, g cmꢀ1): 3196 (N-H), 1669
(C¼O), 1602, 1507, 1479, 1109 (C¼N-N-C¼S). Anal. Calcd. for
C20H13N4O5SCl: C, 52.58; H, 2.87; N, 12.26. Found: C, 52.42; H, 2.79;
N, 12.11.
2-(5-(2-chlorophenyl)-2-furoylamido)-5-(4-nitrophenyloxymethyl)-1,3,4-
thiadiazole(IIj) : White solid. yield: 86%. m.p.: 245–256ꢁC. 1H NMR
(80 MHz, DMSO-d6) d 13.29 (1H, s, NH), 7.06–8.51 (10H, m, Ar-H
and Fu-H), 5.56 (2H, s, CH2). IR(KBr, g cmꢀ1): 3211 (N-H), 1659
(C¼O), 1604, 1514, 1473, 1106 (C¼N-N-C¼S). Anal. Calcd. for
C20H13N4O5SCl: C, 52.58; H, 2.87; N, 12.26. Found: C, 52.50; H, 2.86;
N, 12.30.

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1835
ACKNOWLEDGMENT
The authors thank the Natural Science Foundation of Gansu Province
for the financial support of this work.
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Received in the USA August 24, 2000

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