On reactions of thiadiazinones: Synthesis of new 6-arylidene-1,3,4- thiadiazin-5-ones

Article abstract of DOI:10.1007/s10593-009-0323-6

6-Benzylidene-, 6-(furan-2-ylmethylene)-, and 6-(thiophen-2-ylmethylene)-1, 3,4-thia- diazin-5-ones have been synthesized by condensation of 1,3,4-thiadiazin-5-ones with appropriate aromatic aldehydes.

Full text of DOI:10.1007/s10593-009-0323-6

Chemistry of Heterocyclic Compounds, Vol. 45, No. 6, 2009
ON REACTIONS OF THIADIAZINONES:
SYNTHESIS OF NEW 6-ARYLIDENE-
1,3,4-THIADIAZIN-5-ONES
Hany M. Dalloul1* and Ali Z. El-Shorafa1
6-Benzylidene-, 6-(furan-2-ylmethylene)-, and 6-(thiophen-2-ylmethylene)-1,3,4-thia- diazin-5-ones have
been synthesized by condensation of 1,3,4-thiadiazin-5-ones with appropriate aromatic aldehydes.
Keywords: aromatic aldehydes, 1,3,4-thiadiazin-5-ones, condensation.
Heterocycles containing nitrogen and sulfur constitute the core structure of a number of biologically
interesting compounds. 1,3,4-Thiadiazine derivatives are known to possess various biological and medicinal
activities such as bactericidal [1], fungicidal [2], insecticidal [3], pesticidal [4], herbicidal [5, 6], plant-growth
regulator activity [7], anti-inflammatory [8], antithrombotic [9], antiplatelet [10], anti-arrhythmic [11],
spasmolytic [12, 13], cardiotonic [14, 15], and metalloproteinase inhibitor activity [16]. They have been
proposed for the treatment of heart failures [17]. Moreover, 1,3,4-thiadiazinone derivatives have been used for
prevention and/or treatment of anemia [18], as phosphodiesterase III/IV inhibitors [19, 20], and also for the
treatment of tumors and acquired immune deficiency syndrome (AIDS) [20, 21]. Different methods were used to
synthesize the 1,3,4-thiadiazin-5-one derivatives, some of which employed thiosemicarbazide [22],
thiocarbohydrazide [23], thiooxamic acid derivatives [24] and α-halocarbonyl compounds. Recently, the reactions
of 1,3,4-thiadiazine derivatives have been reviewed [25].
In continuation of our work on the reaction of six-membered thiaaza heterocyclic compounds we report
on the reactivity of 2-aroyl-4-aryl-6H-1,3,4-triazin-5-ones 4a-x towards aromatic aldehydes (see Scheme).
The N-aryl-substituted hydrazonoyl halides 1 are found to react with 2-sulfanyl alkanoic acids [26] or ethyl
sulfanylacetate [27] via reactive nitrilimines 2 yielding acyclic adducts 3a-x which underwent cyclization to
1,3,4-thiadiazinone rings 4a-x in the presence of dicyclohexylcarbodiimide (DCC) or lithium hydride, or
methanolic sodium methoxide. Condensation of these thiadiazinones with benzaldehyde, 2-furaldehyde, and
thiophene-2-carboxaldehyde in the presence of potassium acetate/acetic acid afforded the corresponding
6-benzylidene-, 6-(furan-2-ylmethylene)-, and 6-(thiophen-2-yl-methylene)-1,3,4-thiadiazin-5-ones 5a-x in
moderate yields (Table 1).
_______
* To whom correspondence should be addressed, e-mail: hanydallool@yahoo.com
1
Chemistry Department, Faculty of Applied Science, Al-Aqsa University of Gaza, Gaza 76888, Gaza Strip,
Palestine.
__________________________________________________________________________________________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 918-924, June, 2009. Original
article received April, 15, 2009.
0009-3122/09/4506-0735©2009 Springer Science+Business Media, Inc.
735

The IR spectra of compounds 5a–x in KBr showed strong absorption bands of the aroyl carbonyl group
in the 1690-1640 region, a lactam C=O band in the 1680-1670 region, and C–S band in the 1220-1200 cm–1
region. The 1H NMR spectra of compounds 5a-x showed the disappearance of methylene protons (3.9-3.8 ppm)
at C-6 (present in compounds 4a-x), the methine proton (=CHAr') signal appeared as a singlet in the range of
13
6.2-6.1 and the signal at about 9.0 ppm was attributed to amide N–H proton in compounds 5i-q. The C NMR
spectra of these adducts displayed characteristic signals of the different carbons of the structures suggested. The
signal of carbonyl carbon of lactam (C=O of ring) appeared in the range of 161-160 ppm and that of methine
carbon (=CHAr') resonated in the range of 111-109 ppm. The signal in the range of 147-143 ppm was attributed
to C=N of the thiadiazinone ring.
R
X
X
O
COOR1
O
HS
Et3N
N
N
N
Ar
R = H, Me;
R1 = H,Et
H
N
Ar
–
+
Cl(Br)
X
1
X
2
O
N
S
N
O
N
S
N
DCC or LiH
or MeONa
H
COOR1
R
O
Ar
Ar
R
X
3a–x
4a–x
H
Ar1
O
N
N
O
O
R = H
Ar
S
Ar1
5a–x
Entry
Ar
Me
Me
Me
Me
Me
Me
Ph
Ar1
Entry
Ar
Ar1
X
X
m
n
o
p
q
r
s
t
u
v
w
x
2-Furyl
2-Thienyl
Ph
2-Thienyl
2-Furyl
Ph
2-Furyl
Ph
2-Thienyl
Ph
H
H
Ph
2-Furyl
Cl Ph
Cl 2-Furyl
Br Ph
Br 2-Furyl
Cl Ph
Cl 2-Furyl
Cl
Cl
Br
Br
F
Cl
Cl
Cl
Cl
H
PhNH
PhNH
PhNH
PhNH
PhNH
a
b
c
d
e
f
g
h
i
2-Furyl
2-Furyl
2-Thienyl
2-Thienyl
2-Naphthyl
2-Naphthyl
2-Naphthyl
Ph
H
H
H
Ph
2-Furyl
2-Thienyl
PhNH
PhNH
PhNH
PhNH
j
k
l
Ph
2-Furyl
Me
Me
Cl Ph
In conclusion, the condensation of 2-aroyl-4-aryl-6H-1,3,4-triazin-5-ones with appropriate aromatic
aldehydes gave 6-arylidene-1,3,4-triazin-5-ones in 60-70% yield.
736

TABLE 1 Physical Characteristics and Elemental Analysis Data of
Compounds 5a-x
Found, %
——————
Calculated, %
Com-
pound
Empirical
formula
mp, oC
Yield, %
65
C
H
N
5a
C18H14N2O2S
66.80
67.06
4.20
4.38
8.60
8.69
218-220
5b
5c
5d
5e
5f
C16H12N2O3S
61.20
61.53
60.80
60.59
55.70
55.42
53.50
53.88
49.40
49.12
66.20
65.95
61.40
61.69
69.40
69.15
64.90
64.77
62.00
62.20
63.50
63.67
59.80
59.51
57.50
57.33
57.90
57.75
51.80
52.07
62.10
61.91
61.50
61.69
57.50
57.22
59.60
59.36
53.15
52.95
74.50
74.63
75.20
74.98
71.40
71.22
4.00
3.87
3.50
3.67
3.30
3.20
3.40
3.27
2.60
2.83
3.50
3.61
3.40
3.20
4.60
4.29
4.10
4.88
3.60
3.73
3.90
3.72
3.60
3.38
3.40
3.21
3.60
3.37
3.10
2.90
3.30
3.46
3.40
3.20
2.60
2.78
2.90
3.08
2.75
2.57
4.25
4.18
4.30
4.49
4.30
4.14
9.10
8.97
7.70
7.85
7.90
8.08
7.10
6.98
7.40
7.16
6.60
6.69
6.70
6.85
10.70
10.52
10.90
10.79
10.20
10.36
9.50
9.68
10.10
9.91
9.40
9.55
8.50
8.78
8.50
8.67
10.20
10.31
7.00
6.85
6.90
7.02
6.30
6.59
6.40
6.50
6.35
6.45
6.10
6.25
6.50
6.39
145-147
198-200
147-149
190-191
170-172
190-192
150-152
110-112
164-166
123-125
136-138
190-192
174-176
146-148
128-130
144-146
212-214
158-160
207-209
196-197
216-218
188-190
168-170
61
63
61
65
64
62
60
65
61
67
65
69
63
66
61
68
65
64
62
68
60
61
60
C18H13ClN2O2S
C16H11ClN2O3S
C18H13BrN2O2S
C16H11BrN2O3S
C23H15ClN2O2S
C21H13ClN2O3S
C23H17N3O2S
5g
5h
5i
5j
C21H15N3O3S
5k
5l
C21H15N3O2S2
C23H16ClN3O2S
C21H14ClN3O3S
C21H14ClN3O2S
C23H16BrN3O2S
C21H14BrN2O2S2
C21H14FN3O3S
C21H13ClN2O3S
C19H11ClN2O4S
C21H13ClN2O2S2
C19H11ClN2O2S3
C27H18N2O2S
5m
5n
5o
5p
5q
5r
5s
5t
5u
5v
5w
5x
C28H20N2O2S
C26H18N2O3S
EXPERIMENTAL
Melting points were determined on a Stuart electrothermal apparatus and are uncorrected. The IR
spectra were obtained by using Satellite 3000 Mid IR spectrophotometer in KBr pellets. 1H and 13C NMR spectra
were recorded on a Bruker spectrometer (400 and 100 MHz, respectively) at room temperature in DMSO-d6,
using TMS as an internal reference, and the chemical shifts (δ) were reported in ppm downfield from TMS. The
elemental analysis was performed at Cairo University, Egypt, and the results agreed with the calculated values
within experimental errors.
737

2-Aroyl-4-aryl-1,3,4-thiadiazin-5-ones 4a-x were prepared according to the previous by described
procedures [25, 26]. Benzaldehyde, 2-furaldehyde, and thiophene-2-carboxaldehyde were purchased from
Avocado Research Chemicals, England.
Synthesis of adducts 5a-x (General Method). Molar equivalents of 1,3,4-thiadiazin-5-ones 4a-x and
appropriate aldehyde (1:1 adducts), anhydrous potassium acetate, and glacial acetic acid were dissolved together
at room temperature, and the reaction mixture was heated to reflux temperature with efficient stirring. The
reactions were monitored by thin layer chromatography (TLC) analysis until all the aldehydes reacted. Upon
cooling, the mixture gave a precipitate, which was collected, washed several times with water, and recrystallized
from ethanol.
2-Acetyl-6-benzylidene-4-phenyl-1,3,4-thiadiazin-5-one (5a). IR spectrum, ν, cm–1: 1692 (CH3C=O),
1675 (lactam C=O), 1215 (C–S). 1H NMR spectrum, δ, ppm: 7.81-7.05 (10H, m, H Ar); 6.15 (1H, s, CH); 2.58 (3H,
13
s, CH3). C NMR spectrum, δ, ppm: 192.5 (C=O); 160.3 (lactam C=O); 145.2 (C=N); 142.4; 140.8; 135.2; 130.7;
128.8; 128.2; 127.7; 125.2; 115.2 (8 arom. carbons and C-6); 111.6 (=CH); 26.6 (CH3).
2-Acetyl-6-(furan-2-ylmethylene)-4-phenyl-1,3,4-thiadiazin-5-one (5b). IR spectrum, ν, cm–1: 1695
(CH3C=O), 1677 (lactam C=O), 1217 (C−S). 1H NMR spectrum, δ, ppm: 8.20-7.15 (8H, m, H Ar); 6.22 (1H, s, CH);
2.60 (3H, s, CH3). 13C NMR spectrum, δ, ppm: 192.7 (C=O); 160.2 (lactam C=O); 145.7 (C=N); 142.0; 140.6; 134.8;
132.2; 128.9; 128.4; 127.8; 125.1; 115.4 (8 arom. carbons and C-6); 109.5 (=CH); 26.7 (CH3).
2-Acetyl-6-benzylidene-4-(4-chlorophenyl)-1,3,4-thiadiazin-5-one (5c). IR spectrum, ν, cm–1: 1694
(CH3C=O), 1680 (lactam C=O), 1219 (C−S). 1H NMR spectrum, δ, ppm: 7.84-7.16 (9H, m, H Ar); 6.18 (1H, s, CH);
2.56 (3H, s, CH3). 13C NMR spectrum, δ, ppm: 192.6 (C=O); 160.7 (lactam C=O); 146.3 (C=N); 142.9; 139.1; 135.0;
133.5; 129.0; 127.4; 126.4; 121.0; 116.6 (8 arom. carbons and C-6); 111.8 (=CH), 26.6 (CH3).
2-Acetyl-4-(4-chlorophenyl)-6-(furan-2-ylmethylene)-1,3,4-thiadiazin-5-one (5d). IR spectrum, ν, cm-1:
1
3336 (N–H), 1692 (CH3C=O), 1682 (lactam C=O), 1214 (C−S). H NMR spectrum, δ, ppm: 7.82–7.18 (7H, m,
H Ar); 6.20 (1H, s, CH); 2.55 (3H, s, CH3). 13C NMR spectrum, δ, ppm: 192.5 (C=O); 160.8 (lactam C=O); 146.9
(C=N); 142.4; 139.1; 135.3; 133.4; 129.1; 128.2; 127.9; 126.3; 116.2 (8 arom. carbons and C-6); 110.3 (=CH), 26.7
(CH3).
2-Acetyl-6-benzylidene-4-(4-bromophenyl)-1,3,4-thiadiazin-5-one (5e). IR spectrum, ν, cm–1: 1695
(CH3C=O), 1675 (lactam C=O), 1221 (C−S). 1H NMR spectrum, δ, ppm: 8.49-7.10 (9H, m, H Ar); 6.17 (1H, s, CH);
2.57 (3H, s, CH3). 13C NMR spectrum, δ, ppm: 192.7 (C=O); 160.5 (lactam C=O); 146.6 (C=N); 142.6; 139.7; 135.2;
132.0; 128.9; 128.1; 126.6; 121.4; 117.0 (8 arom. carbons and C-6); 111.5 (=CH); 26.6 (CH3).
2-Acetyl-4-(4-bromophenyl)-6-(furan-2-ylmethylene)-1,3,4-thiadiazin-5-one (5f). IR spectrum, ν, cm-1:
1693 (CH3C=O), 1673 (lactam C=O), 1219 (C−S). 1H NMR spectrum, δ, ppm: 8.22-7.05 (7H, m, H Ar); 6.23 (1H, s,
CH); 2.54 (3H, s, CH3). 13C NMR spectrum, δ, ppm: 192.6 (C=O); 160.8 (lactam C=O); 146.4 (C=N); 142.8; 139.6;
135.5; 131.9; 128.1; 127.6; 126.4; 121.1; 117.2 (8 arom. carbons and C-6); 109.3 (=CH), 26.7 (CH3).
2-Benzoyl-6-benzylidene-4-(4-chlorophenyl)-1,3,4-thiadiazin-5-one (5g). IR spectrum, ν, cm–1: 1678
(lactam C=O), 1650 (C=O), 1205 (C−S). 1H NMR spectrum, δ, ppm: 8.27-7.16 (14H, m, H Ar); 6.28 (1H, s, CH).
13C NMR spectrum, δ, ppm: 185.6 (C=O); 161.2 (lactam C=O); 142.9 (C=N); 141.3; 140.6; 138.3; 137.9; 135.3;
134.8; 132.4; 129.5; 127.9; 127.5; 126.1; 125.6; 124.6 (12 arom. carbons and C-6); 111.9 (=CH).
2-Benzoyl-4-(4-chlorophenyl)-6-(furan-2-ylmethylene)-1,3,4-thiadiazin-5-one (5h). IR spectrum, ν, cm–1:
1676 (lactam C=O), 1653 (C=O), 1207 (C−S). 1H NMR spectrum, δ, ppm: 8.24-7.12 (12H, m, H Ar); 6.27 (1H, s,
13
CH). C NMR spectrum, δ, ppm: 185.4 (C=O); 161.1 (lactam C=O); 142.8 (C=N); 141.5; 140.4; 138.7; 137.9;
135.1; 134.8; 130.9; 129.4; 128.0; 127.6; 125.2; 124.4; 120.6 (12 arom. carbons and C-6); 110.4 (=CH).
6-Benzylidene-4-phenyl-2-phenylaminocarbonyl-1,3,4-thiadiazin-5-one (5i). IR spectrum, ν, cm–1: 3258
1
(N−H), 1679 (lactam C=O), 1655 (amide C=O), 1205 (C−S). H NMR spectrum, δ, ppm: 9.20 (1H, s, NH);
7.59-7.12 (15H, m, H Ar); 6.11 (1H, s, CH). 13C NMR spectrum, δ, ppm: 160.3 (lactam C=O); 157.7 (amide C=O);
145.0 (C=N); 141.5; 138.7; 137.6; 135.2; 135.0; 128.9; 128.6; 127.9; 127.5; 125.1; 124.5; 121.0; 113.7 (12 arom.
carbons and C-6); 111.1 (=CH).
738

6-(Furan-2-ylmethylene)-4-phenyl-2-phenylaminocarbonyl-1,3,4-thiadiazin-5-one (5j). IR spectrum, ν,
1
cm-1: 3260 (N–H), 1676 (lactam C=O), 1650 (amide C=O), 1208 (C–S). H NMR spectrum, δ, ppm: 9.15 (1H, s,
NH); 7.72-7.16 (13H, m, H Ar); 6.13 (1H, s, CH). 13C NMR spectrum, δ, ppm: 160.6 (lactam C=O); 158.2 (amide
C=O); 144.7 (C=N); 141.3; 138.9; 137.9; 135.2; 134.8; 130.4; 128.7; 128.5; 127.6; 126.5; 124.3; 123.3; 114.4 (12
arom. carbons and C-6); 110.9 (=CH).
4-Phenyl-2-phenylaminocarbonyl-6-(thiophen-2-ylmethylene)-1,3,4-thiadiazin-5-one (5k). IR spectrum,
ν, cm–1: 3255 (N−H), 1678 (lactam C=O), 1652 (amide C=O), 1202 (C−S). 1H NMR spectrum, δ, ppm: 9.17 (1H, s,
NH); 7.76-7.20 (13H, m, H Ar); 6.10 (1H, s, CH). 13C NMR spectrum, δ, ppm: 160.8 (lactam C=O); 158.5 (amide
C=O); 145.1 (C=N); 141.5; 138.2; 134.7; 131.4; 129.1; 128.8; 128.0; 127.8; 127.2; 124.5; 121.8; 114.7 (12 arom.
carbons and C-6); 110.3 (=CH).
6-Benzylidene-4-(4-chlorophenyl)-2-phenylaminocarbonyl-1,3,4-thiadiazin-5-one (5l). IR spectrum, ν,
1
cm–1: 3257 (N−H), 1680 (lactam C=O), 1660 (amide C=O), 1207 (C−S). H NMR spectrum, δ, ppm: 9.33 (1H, s,
NH); 7.50-7.05 (14H, m, H Ar); 6.12 (1H, s, CH). 13C NMR spectrum, δ, ppm: 160.7 (lactam C=O); 157.9 (amide
C=O); 143.9 (C=N); 141.0; 139.0; 138.6; 135.0; 130.4; 129.1; 128.6; 128.3; 126.4; 124.2; 123.3; 120.1; 115.8 (12
arom. carbons and C-6); 111.3 (=CH).
4-(4-Chlorophenyl)-6-(furan-2-ylmethylene)-2-phenylaminocarbonyl-1,3,4-thia- diazin-5-one (5m). IR
1
spectrum, ν, cm–1: 3265 (N−H), 1682 (lactam C=O), 1665 (amide C=O), 1205 (C−S). H NMR spectrum, δ, ppm:
13
9.25 (1H, s, NH); 7.64-7.13 (12H, m, H Ar); 6.16 (1H, s, CH). C NMR spectrum, δ, ppm: 160.1 (lactam C=O);
157.7 (amide C=O); 144.5 (C=N); 140.2; 139.5; 138.9; 135.2; 130.5; 128.7; 128.5; 127.7; 125.8; 124.4; 123.2;
120.2; 116.5 (12 arom. carbons and C-6); 110.9 (=CH).
4-(4-Chlorophenyl)-2-phenylaminocarbonyl-6-(thiophen-2-ylmethylene)-1,3,4-thiadiazin-5-one (5n).
IR spectrum, ν, cm–1: 3258 (N−H), 1679 (lactam C=O), 1660 (amide C=O), 1204 (C−S). 1H NMR spectrum, δ, ppm:
13
9.23 (1H, s, NH); 7.68-7.20 (12H, m, H Ar); 6.14 (1H, s, CH). C NMR spectrum, δ, ppm: 160.2 (lactam C=O);
158.1 (amide C=O); 144.1 (C=N); 140.6; 139.6; 138.6; 135.0; 130.2; 129.6; 128.9; 128.2; 127.9; 124.2; 123.0;
120.8; 116.8 (arom. carbons and C-6); 110.5 (=CH).
6-Benzylidene-4-(4-bromophenyl)-2-phenylaminocarbonyl-1,3,4-thiadiazin-5-one (5o). IR spectrum, ν,
1
cm–1: 3246 (N−H), 1682 (lactam C=O), 1650 (amide C=O), 1211 (C−S). H NMR spectrum, δ, ppm: 9.19 (1H, s,
NH); 7.49-7.11 (14H, m, H Ar); 6.16 (1H, s, CH). 13C NMR spectrum, δ, ppm: 160.8 (lactam C=O); 158.0 (amide
C=O); 144.7 (C=N); 141.0; 139.9; 138.4; 137.5; 135.1; 131.4; 128.8; 127.8; 127.6; 125.8; 124.5; 121.1; 118.5 (12
arom. carbons and C-6); 111.1 (=CH).
4-(4-Bromophenyl)-2-phenylaminocarbonyl-6-(thiophen-2-ylmethylene)-1,3,4-thiadiazin-5-one (5p).
IR spectrum, ν, cm–1: 3249 (N−H), 1683 (lactam C=O), 1655 (amide C=O), 1210 (C−S). 1H NMR spectrum, δ, ppm:
13
9.26 (1H, s, NH); 7.51-7.13 (12H, m, H Ar); 6.15 (1H, s, CH). C NMR spectrum, δ, ppm: 160.9 (lactam C=O);
158.2 (amide C=O); 144.3 (C=N); 141.3; 139.1; 138.6; 137.7; 135.3; 131.2; 129.1; 128.4; 127.1; 126.6; 124.1;
120.9; 118.4 (12 arom. carbons and C-6); 110.3 (=CH).
4-(4-Fluorophenyl)-6-(furan-2-ylmethylene)-2-phenylaminocarbonyl-1,3,4-thiadiazin-5-one (5q). IR
1
spectrum, ν, cm–1: 3245 (N−H), 1681 (lactam C=O), 1650 (amide C=O), 1213 (C−S). H NMR spectrum, δ, ppm:
13
9.12 (1H, s, NH); 7.48-7.14 (12H, m, H Ar); 6.18 (1H, s, CH). C NMR spectrum, δ, ppm: 160.7 (lactam C=O);
158.1 (amide C=O); 144.1 (C=N); 140.6; 139.4; 138.4; 135.5; 132.2; 129.3; 128.7; 128.2; 127.4; 125.4; 120.2;
116.6; 115.7 (12 arom. carbons and C-6); 110.2 (=CH).
6-Benzylidene-4-(4-chlorophenyl)-2-furoyl-1,3,4-thiadiazin-5-one (5r). IR spectrum, ν, cm–1: 1682
(lactam C=O), 1660 (C=O), 1213 (C−S). 1H NMR spectrum, δ, ppm: 7.84-7.16 (12H, m, H Ar); 6.20 (1H, s, CH).
13C NMR spectrum, δ, ppm: 173.5 (C=O); 161.3 (lactam C=O); 145.3 (C=N); 142.9; 139.7; 134.9; 130.4; 129.8;
129.0; 128.9; 128.6; 127.3; 125.1; 123.7; 120.6; 115.0 (12 arom. carbons and C-6); 111.3 (=CH).
4-(4-Chlorophenyl)-6-(furan-2-ylmethylene)-2-(2-furoyl)-1,3,4-thiadiazin-5-one (5s). IR spectrum, ν,
1
cm–1: 1682 (lactam C=O), 1665 (C=O), 1215 (C−S). H NMR spectrum, δ, ppm: 7.82-7.14 (10H, m, H Ar); 6.21
13
(1H, s, CH). C NMR spectrum, δ, ppm: 173.4 (C=O); 161.0 (lactam C=O); 145.7 (C=N); 142.3; 139.6; 135.2;
132.2; 130.9; 129.8; 129.1; 128.8; 127.6; 125.3; 123.7; 120.8; 114.9 (12 arom. carbons and C-6); 110.7 (=CH).
739

6-Benzylidene-4-(4-chlorophenyl)-2-thenoyl-1,3,4-thiadiazin-5-one (5t). IR spectrum, ν, cm–1: 1682
(lactam C=O), 1660 (C=O), 1217 (C−S). 1H NMR spectrum, δ, ppm: 7.76-7.12 (12H, m, H Ar); 6.16 (1H, s, CH).
13C NMR spectrum, δ, ppm: 174.7 (amide C=O); 161.1 (lactam C=O); 144.6 (C=N); 141.5; 140.2; 138.9; 135.2;
135.0; 130.4; 128.7; 128.5; 126.7; 124.3; 123.5; 120.2; 115.9 (12 arom. carbons and C-6); 111.3 (=CH).
4-(4-Clorophenyl)-6-(thiophen-2-ylmethylene)-2-(2-thenoyl)-1,2,4-thiadiazin-5-one (5u). IR spectrum, ν,
1
cm–1: 1682 (lactam C=O), 1651 (C=O), 1216 (C−S). H NMR spectrum, δ, ppm: 7.78-7.16 (10H, m, H Ar); 6.12
13
(1H, s, CH). C NMR spectrum, δ, ppm: 174.8 (C=O); 161.3 (lactam C=O); 144.1 (C=N); 141.3; 139.9; 138.6;
135.4; 135.1; 130.2; 128.9; 128.2; 126.1; 124.6; 123.9; 120.3; 115.8 (12 arom. carbons and C-6); 110.6 (=CH).
6-Benzylidene-2-(2-naphthoyl)-4-phenyl-1,3,4-thiadiazin-5-one (5v). IR spectrum, ν, cm–1: 1682 (lactam
C=O), 1646 (C=O), 1201 (C−S). 1H NMR spectrum, δ, ppm: 8.85-7.24 (17H, m, H Ar); 6.15 (1H, s, CH). 13C NMR
spectrum, δ, ppm: 184.7 (C=O); 161.0 (lactam C=O); 147.7 (C=N); 142.4; 140.8; 138.7; 137.5; 135.6; 134.9; 132.6;
132.4; 129.9; 128.9; 128.6; 128.0; 127.7; 127.2; 126.6; 125.5; 124.5; 121.0; 115.6 (18 arom. carbons and C-6); 111.4
(=CH).
6-Benzylidene-4-(4-methylphenyl)-2-(2-naphthoyl)-1,3,4-thiadiazin-5-one (5w). IR spectrum, ν, cm–1:
1682 (lactam C=O), 1642 (C=O), 1204 (C−S). 1H NMR spectrum, δ, ppm: 8.83-7.25 (16H, m, H Ar); 6.11 (1H, s,
CH); 2.27 (3H, s, CH3). 13C NMR spectrum, δ, ppm: 184.4 (C=O); 160.7 (lactam C=O); 147.3 (C=N); 142.2; 140.4;
139.7; 138.7; 137.5; 135.6; 132.9; 132.6; 130.4; 129.7; 128.9; 128.6; 128.0; 127.7; 127.3; 126.6; 125.5; 124.5; 114.0
(18 arom. carbons and C-6); 111.6 (=CH), 21.7 (CH3).
6-(Furan-2-ylmethylene)-4-(4-methylphenyl)-2-(2-naphthoyl)-1,3,4-thiadiazin-5-one (5x). IR spectrum,
ν, cm–1: 1682 (lactam C=O), 1645 (C=O), 1202 (C–S). 1H NMR spectrum, δ, ppm: 8.86-7.27 (14H, m, H Ar); 6.12
(1H, s, CH); 2.26 (3H, s, CH3). 13C NMR spectrum, δ, ppm: 184.5 (C=O); 160.8 (lactam C=O); 146.9 (C=N); 142.2;
140.8; 138.7; 137.5; 135.6; 132.9; 132.6; 132.4; 129.9; 128.9; 128.6; 128.0; 127.7; 127.4; 126.6; 125.5; 124.5;
121.0; 113.8 (18 arom. carbons and C-6); 109.9 (=CH), 21.9 (CH3).
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