Synthesis of quinoline-based thieno-seleno-phenylquinazolinones

Article abstract of DOI:10.1080/10426500802176945

The synthesis of quinoline-substituted phenylquinazolinones containing sulfur and selenium is described. These molecules were isolated from a series of reactions of 2-phenyl-4H-3,1-benzoxazin-4-one with 2-chloro, 2-thieno, and 2-selenoquinoline-3-carbalde

Full text of DOI:10.1080/10426500802176945

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Phosphorus, Sulfur, and Silicon
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Synthesis of Quinoline-
Based Thieno-Seleno-
Phenylquinazolinones
H. R. Prakash Naik a , H. S. Bhojya Naik a , T. R.
Ravikumar Naik a , M. Raghavendra a , T. Aravinda a
& D. S. Lamani a
a Dept. of PG Studies and Research in Industrial
Chemistry, School of Chemical Sciences , Kuvempu
University , Shankaraghatta, Karnataka, India
Published online: 04 Feb 2009.
To cite this article: H. R. Prakash Naik , H. S. Bhojya Naik , T. R. Ravikumar Naik ,
M. Raghavendra , T. Aravinda & D. S. Lamani (2009) Synthesis of Quinoline-Based
Thieno-Seleno-Phenylquinazolinones, Phosphorus, Sulfur, and Silicon and the Related
Elements, 184:2, 460-470, DOI: 10.1080/10426500802176945
To link to this article: http://dx.doi.org/10.1080/10426500802176945
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Phosphorus, Sulfur, and Silicon, 184:460–470, 2009
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500802176945
Synthesis of Quinoline-Based
Thieno-Seleno-Phenylquinazolinones
H. R. Prakash Naik, H. S. Bhojya Naik, T. R. Ravikumar
Naik, M. Raghavendra, T. Aravinda, and D. S. Lamani
Dept. of PG Studies and Research in Industrial Chemistry, School of
Chemical Sciences, Kuvempu University, Shankaraghatta,
Karnataka, India
The synthesis of quinoline-substituted phenylquinazolinones containing sulfur and
selenium is described. These molecules were isolated from a series of reactions of
2-phenyl-4H-3,1-benzoxazin-4-one with 2-chloro, 2-thieno, and 2-selenoquinoline-
3-carbaldehyde hydrazones. The structure of the isolated compounds has been elu-
1
cidated on the basis of IR, H NMR, mass spectral, and elemental analysis data.
Keywords Phenylquinazolinone; quinoline; selenium; sulfur
INTRODUCTION
It has been more than a century since the initial studies on 4(3H)-
quinazolinones[1],1 and they are well known as biologically active
compounds.2 Several 2-styrylquinazolin-4(3H)-ones have been pre-
pared since 19103 and are active against certain types of cancers.4
Perydylvinyl-4(3H)-quinazolinones[2] showed anticonvulsant, hyp-
notic, tranquilizing, and muscle relaxant activity.5 The atropisomers,
2-(2-heteroarylvinyl)-3-aryl-6-fluro-4(3H)-quinazolinone[3], known as
AMPA (α-amino-3hydroxy-5-methyl-4-isoxazolepropanoic acid) re-
ceptor antagonists,6 2,6-disubstituted 4(3H)-quinazolinones[4] are
known as trace membrane receptor antagonists and their activ-
ity, has been subjected to extensive molecular modeling.7 Various
2- and 3-disubstituted quinazolines (C-2, N-3) have been studied
Received 4 April 2008; accepted 2 May 2008.
One of the authors (H.R. Prakash Naik) thanks the Indian Institute of Science for pro-
viding facilities for spectral analyses and SC/ST cell, Kuvempu University for awarding
the Junior Research Fellowship (JRF).
Address correspondence to H. S. Bhojya Naik, Dept. of PG Studies and Research in In-
dustrial Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta-
577 451, Karnataka, India. E-mail: hsb naik@rediffmail.com
460

Quinoline-Based Thieno-Seleno-Phenylquinazolinones
461
their interesting pharmacological activities such as analgesic, anti-
inflammatory,8 antibacterial,9 anticonvulsant,10 antihypertensive,11
and antimalarial activities,12 etc. Treatments of diabetic complica-
tions such as cataracts, nephropathy, and neuropathy,13 and signif-
icant anti-Parkinsonian activity against tremor, rigidity, hypokine-
sia, and catatonia has been evaluated in vivo in rats and mice of
quinazolinylthiazolidinone14 and anticancer15 activities. Recent mod-
eling and quantitative structure-activity relationships (QSAR) studies
include quinazolinone inhibitors of poly (ADP-ribose) polymerase,16 in-
dicating that quinazolinone drug design is approaching the preclinical
stage (Scheme 1).
O
O
R3
N
N
R1
CH3
N
R2
N
[ ]
1
N
[ ]
2
Cl
N
O
N
F
O
N
X
Y
HN
NH
COOH
H
N
N
CH3
CH3
[ ]
4
[ ]
3
N
N
H
_
NH
(CH2CH=CH)-n
R
SO2
X =
Y =
N
R
CO_
N
H
NH
(CH2)-n
SCHEME 1 Various structures of standard drugs possessing quinazoline moi-
ety.
Further, it is well known that number of heterocyclic compounds
containing S and Se exhibit a wide variety of biological activities. Even

462
H. R. P. Naik et al.
though sulfur and selenium are considered to be isosteric as defined by
Longmuir17 and Erlenmeyer,18 the reports about selenium-containing
heterocycles are few.19–21 However, the medicinal application of isos-
terism has been reviewed by Klayman and Gunther.22 The antioxidant
and anticancer activity of selenium-containing compounds have been
reported23–25 recently. Selenium plays an important role in decreasing
oxidative stress in HIV-affected cells and possibly suppresses the rate
of HIV replication.26,27 Recent research proposes that HIV may be ca-
pable of incorporating host selenium into viral selenoproteins that have
glutathione-peroxide activity. Though the significance of these findings
requires further clarification, they suggest that both the human im-
mune system and the activity of the virus are affected by selenium
nutritional status.28,29 In recent years, the number of publications de-
voted to various aspects of fused heterocycles containing sulfur and
selenium has sharply increased.
Due to great pharmacological importance and with the above facts,
we carried out the synthesis of some new heterocycles such as sulfur-
and selenium-containing phenylquinazolinones through a nitrogen
bridge in order to enhance the biological activity.
RESULTS AND DISCUSSION
Numerous condensed quinolines and quinazolines offer valuable phar-
macological activities as mentioned earlier, and, therefore, they are
useful materials in drug research. Hence, in continuation of our study
in developing condensed quinoline derivatives, it appeared expedient
to synthesize a series of systematically condensed and appropriately
functionalized quinoline-substituted phenylquinazolines.
In the present work, an attempt has been made to undertake the
synthesis of (6b–d), (7b–d), and (8b–d) derivatives through a multi-
step processes. The required starting compounds 2a–d and 3a–d were
synthesized according to the reported methods.30 To achieve these tar-
geted molecules, the required compounds, 2-phenyl-4-3,1-benzoxazin-
4-ones (5a–d), were prepared by a cyclization reaction between an-
thranilic acid and benzoyl chloride using pyridine as a solvent and
also as a base. The formation of (5a–d) was confirmed by a sharp
band at 1715 cm−1 for C O group along with a peak at 1178 cm−1
for C O stretching in IR spectra. Then 5a–d was converted to (6a),
(7a), and (8a) through its nucleophilic substitution reaction with 4a–d.
The insertion of nitrogen in the ring of 5a was characterized by the
disappearance of an absorption band at 1178 cm−1 of C O and shift
of carbonyl (C O) absorption bands from 1710, 1716, and 1720 cm−1

Quinoline-Based Thieno-Seleno-Phenylquinazolinones
463
in the series of chlorine, sulfur, and selenium containing 4a–d. The
accession of targeted compound (6a), (7a), and (8a) were confirmed by
1
the disappearance of singlets in H NMR at δ 5.54, 5.42, and 5.45 of
the NH2 group. This shows the formation of desired compounds (6a),
(7a), and (8a) from 4a–d. Finally the formation of the desired series
(6a), (7a), and (8a) were confirmed by means of obtained molecular ion
peaks at 410[M]+, 408[M]+, and 455[M]+ in mass spectra. Similarly
other compounds in the (6b–d), (7b–d), and (8b–d) series are also elu-
cidated on the basis of IR, 1H NMR, mass spectral data, and elemental
analysis (Scheme 2).
CONCLUSION
In conclusion, we developed a versatile and useful new access to a
different scaffold of biologically important quinoline-based sulfur- and
selenium-containing phenylquinazolinones (6a–d), (7a–d), and (8a–d)
using an efficient and simple methodology based on a cyclization, con-
densation technique. However, the availability and simplicity of the
starting materials and the experimental procedure itself make this
path more flexible to obtain a high yield of phenylquinazolines. Fur-
ther research is underway to use this procedure to synthesize other
derivatives.
MATERIALS AND METHODS
General Procedure
The purity of the compounds was checked by thin layer chromatog-
raphy (TLC) on silica gel plates using petroleum ether: ethyl acetate
solvent. Melting points were determined in open capillary tubes and
are uncorrected. IR spectra were recorded in KBr pellets on a Perkin-
1
Elmer 157 IR spectrophotometer. H NMR spectra were recorded in
DMSO-d6 on an EM-390(300 MHz) NMR spectrometer, and mass spec-
tra were recorded on a MASPEC low resolution instrument operating
at 70 eV.
2-Mercaptoquinoline-3-carbaldehyde (2a)
Yield 70%, m.p. 160◦C; IR (KBr) cm−1; 3020 (C H, Ar-H); 1710 (C O),
1583 (C N), 2593 (S H); 1H NMR (DMSO d6), δ 10.1 (s, 1H, CHO), 8.8
(s, 1H, H-4), 8.1 (d, 1H, H-5), 8.0 (d, 1H, H-8), 7.9 (dt, 1H, H-6), 7.7 (dt,
1H, H-7); MS: m/z 189 [M]+; Anal. Calcd. For (C10H7NOS) %: C, 63.47;
H, 3.73; N, 7.40. Found: C, 63.44; H, 3.69; N, 7.42.

464
H. R. P. Naik et al.
O
O
R
R
R
R
5
6
5
6
Na S/ethanol
2
Stirred/1-2 hrs
SH
N
N
Cl
2a-d
1a-d
NaHSe
NH NH . H
O
2
2
2
NH NH . H
stirred
O
2
2
2
stirred
O
R
R
5
SeH
N
3a-d
6
R
R
O
NH NH . H
O
1
4
2
2
2
R
2
stirred
OH
NH
R
R
O
1
4
R
3
2
R
NH
R
5
6
2
2
3
N
O
+
Pyridine
R
N
4a-d
R
R
N
+
R = Cl, SH, SeH
5a-d
Cl
Pyridine
in catalytic amount
O
abs. alcohol
R
R
N
6
R
R
O
N
1
4
R
N
2
R
N
5
R
3
R = Cl, SH, SeH
6a-d, 7a-d and 8a-d
(6a), (7a) and (8a) : R1=R2=R3=R4= H. R5=R6= H.
(6b), (7b) and (8b) : R1= R2= R4= H, R3= CH3. R5=H, R6=OCH3.
(6c), (7c) and (8c) : R1= R2= R4= H, R3=NO2. R5=H, R6=OCH3.
(6d), (7d) and (8d) : R1= R2= R4= H, R3=Cl. R5=H, R6= Cl
SCHEME 2 Synthetic route for the synthesis of phenylquinazolines (6a–d),
(7a–d), and (8a–d).

Quinoline-Based Thieno-Seleno-Phenylquinazolinones
465
2-Selenoquinoline-3-carbaldehyde (3a)
Yield 70%, m.p. 185◦C; IR (KBr) cm−1; 3020 (C H, Ar-H); 1710 (C O),
1583 (C N), 2598 (Se-H); 1H NMR (DMSO d6), δ 10.1 (s, 1H, CHO), 8.7
(s, 1H, H-4), 8.3 (d, 1H, H-5), 8.0 (d, 1H, H-8), 7.8 (dt, 1H, H-6), 7.5 (dt,
1H, H-7); MS: m/z 236 [M]+; Anal. Calcd. For (C10H7NOSe) %: C, 63.47;
H, 3.73; N, 7.40. Found: C, 63.44; H, 3.69; N, 7.42.
General Procedure for the Synthesis of 2-Chloro, 2-Mercapto,
2-Selenoquinoline-3-carbaldehyde hydrazone (4a–c)
A hydrazine hydrate solution (80%, 0.02 mol) was added dropwise at
room temperature and with stirring over 1–2 h to an ethanolic solution
containing 1.91 g, 1.89 g, and 2.36 g of 2-chloro, 2-mercapto, and 2-
seleno quinoline-3-carbaldehydes (0.01 mol). The resulting yellow and
brown colored solid was washed with diethyl ether, filtered, and dried
under vacuum and recrystallized from methanol.
2-Chloro-3-(hydrazinomethyl)quinoline (4a)
Yield 80%, m.p. 135◦C; IR (KBr) cm−1; 3015 (C H, Ar-H); 1590
1
(C N), 830 (C-Cl); H NMR (DMSO d6), δ 8.0 (s, 1H, H-4), 7.5 (s, 1H),
8.7 (s, 1H, CHN), 5.54 (s, 2H, NH2); MS: m/z 205 [M]+; Anal. Calcd. For
(C10H8Cl N3) %: C, 58.41; H, 3.92; N, 20.43. Found: C, 58.44; H, 3.89;
N, 20.45.
2-Mercaptoquinoline-3-carbaldehyde hydrazone (4b)
Yield 75%, m.p. 145◦C; IR (KBr) cm−1; 3018 (C H, Ar-H); 1598
(C N), 2585 (S-H); 1H NMR (DMSO d6), δ 7.9 (s, 1H, H-4), 7.5 (s,
1H, C-4), 8.9 (s, 1H, CHN), 5.42 (s, 2H, NH2), 10.5 (s, 1H, SH); MS: m/z
203 [M]+; Anal. Calcd. For (C10H9N3S) %: C, 59.09; H, 4.46; N, 20.67.
Found: C, 59.03; H, 4.53; N, 20.69.
2-Selenoquinoline-3-carbaldehyde hydrazone (4c)
Yield 75%, m.p. 173◦C ; IR (KBr) cm−1; 3016 (C H, Ar-H); 1591
1
(C N), 2583 (S-H); H NMR (DMSO d6), δ 7.8 (s, 1H, H-4), 7.6 (s, 1H,
C-4), 8.9 (s, 1H, CHN), 5.45 (s, 2H, NH2), 11.3 (s, 1H, SeH); MS: m/z
250 [M]+; Anal. Calcd. For (C10H9N3Se) %: C, 59.09; H, 4.46; N, 20.67.
Found: C, 59.03; H, 4.53; N, 20.69.
2-Phenyl-4H-3,1-benzoxazin-4-one (5a)
Yield 63%, m.p. 115◦C; IR (KBr) cm−1; 3028 (C H, Ar-H); 1715 (C O),
1590 (C N), 1178 (C-O); 1H NMR (DMSO d6), δ 7.6 (m, 9H, Ar-H); MS:

466
H. R. P. Naik et al.
m/z 223 [M]+; Anal. Calcd. For (C14H9NO2) %: C, 75.33; H, 4.03; N,
60.27. Found: C, 75.29; H, 4.01; N, 60.25.
General Procedure for the Synthesis of
3-{[(1)-(2-Chloroquinolin-3-yl)methylene]amino}-2-
phenylquinazolin-4(3H)-one (6a–d), (7a–d), and (8a–d)
A mixture containing 2.23 g of 2-phenyl-4H-3,1-benzoxazin-4-one (0.01
mol) and 2.05 g, 2.03 g, and 2.50 g of 2-chloro, 2-mercapto, 2-
selenoquinoline-3-carbaldehyde hydrazone (0.01 mol) was dissolved in
ethanol, and to this was added a catalytic amount of pyridine. The re-
action mass was refluxed for 4–5 h. Then the cooled reaction mixture
was poured on crushed ice, and the obtained yellow-, brown-, and dark
brown-colored precipitate was filtered and recrystallized from ethanol.
3-{[(2-Chloroquinolin-3-yl)methylidene]amino}-2-
phenylquinazolin-4(3H)-one (6a)
Yield 75%, m.p. 165◦C; IR (KBr) cm−1; 3015 (C H, Ar-H); 1588
1
(C N), 1710 (C O), 1360 (C N); H NMR (DMSO d6), δ 7.1–8.0 (m,
14H, Ar-H), 8.7 (s, 1H, CHN); MS: m/z 410 [M]+; Anal. Calcd. For
(C24H15Cl N4O) %: C, 70.16; H, 3.68; N, 13.64. Found: C, 70.14; H, 3.61;
N, 13.69.
3-{[(2-Chloro-7-methoxyquinolin-3-yl)methylene]amino}-7-
methyl-2-phenylquinazolin-4(3H)-one (6b)
Yield 75%, m.p. 185◦C; IR (KBr) cm−1; 3029(C H, Ar-H); 1620 (C N),
1681 (C O), 1318 (C-N), 1182 (C-O-C), 2975 (C H, CH3); 1H NMR
(DMSO d6), δ 7.5 (m, 12H, Ar-H), 3.93 (s, 3H, OCH3), 2.4 (s, 3H, CH3),
8.3 (s, 1H, CHN); MS: m/z 454 [M]+; Anal. Calcd. for (C26H19Cl N4O2)
%: C, 68.65; H, 4.21; N, 12.32. Found: C, 68.63; H, 4.25; N, 12.35.
3-{[(2-Chloro-7-methoxyquinolin-3-yl)methylene]amino}-7-
nitro-2-phenylquinazolin-4(3H)-one (6c)
Yield 75%, m.p. 169◦C; IR (KBr) cm−1; 3021(C H, Ar-H); 1615 (C N),
1675 (C O), 1331 (C-N),1185 (C-O-C), 1390 (NO2), 2975 (C H, CH3);
1H NMR (DMSO d6), δ 7.5 (m, 10H, Ar-H), 8.6 (s, 2H), 3.89 (s, 3H,
OCH3), 8.5 (s, 1H, CHN); MS: m/z 485 [M]+; Anal. Calcd. For (C25H16Cl
N5O4) %: C, 61.80; H, 3.32; N, 14.41. Found: C, 61.78; H, 3.35; N, 14.40.
7-Chloro-3-{[(2,7-dichloroquinolin-3-yl)methylene]amino}-2-
phenylquinazolin-4(3H)-one (6d)
Yield 75%, m.p. 161◦C; IR (KBr) cm−1; 3013(C H, Ar-H); 1590 (C N),
748 (C-Cl), 1710 (C O), 1370 (C-N); 1H NMR (DMSO d6), δ 7.4 (m, 8H,
Ar-H), 6.9 (s, 4H, H-4), 8.5 (s, 1H, CHN); MS: m/z 479 [M]+; Anal. Calcd.

Quinoline-Based Thieno-Seleno-Phenylquinazolinones
467
For (C24H13Cl3 N4O) %: C, 60.09; H, 2.73; N, 11.68. Found: C, 60.11; H,
2.76; N, 11.64.
3-{[(2-Mercaptoquinolin-3-yl)methylene]amino}-2-phenyl
quinazolin-4(3H)-one (7a)
Yield 68%, m.p. 171◦C; IR (KBr) cm−1; 3019 (C H, Ar-H); 1602
(C N), 1716 (C O), 1345 (C-N); 1H NMR (DMSO d6) δ 7.0–7.9 (m,
14H, Ar-H), 10.1 (s, 1H, SH), 8.7 (s, 1H, CHN); MS: m/z 408 [M]+; Anal.
Calcd. For (C24H16N4OS) %: C, 70.57; H, 3.95; N, 13.72. Found: C, 70.52;
H, 3.90; N, 13.68.
3-{[(2-Mercapto-7-methoxyquinolin-3-yl)methylene]amino}-7-
methyl-2-phenylquinazolin-4(3H)-one (7b)
Yield 68%, m.p. 176◦C; IR (KBr) cm−1; 3018(C H, Ar-H); 1625 (C N),
1679 (C O), 1300 (C-N), 1395 (NO2); 1H NMR (DMSO d6), δ 7.1–8.0 (m,
12H, Ar-H), 3.81 (s, 3H, OCH3), 10.3 (s, 1H, SH), 2.2 (s, 3H, CH3), 8.5
(s, 1H, CHN); MS: m/z 452 [M]+; Anal. Calcd. For (C26H20N4O2S) %: C,
69.01; H, 4.45; N, 12.38. Found: C, 69.05; H, 4.41; N, 12.41.
3-{[(2-Mercapto-7-methoxyquinolin-3-yl)methylene]amino}-7-
nitro-2-phenylquinazolin-4(3H)-one (7c)
Yield 68%, m.p. 183◦C; IR (KBr) cm−1; 3025(C H, Ar-H); 1611 (C N),
1695 (C O), 1321 (C-N), 1395 (NO2); 1H NMR (DMSO d6), δ 7.1–7.9 (m,
10H, Ar-H), 8.5 (s, 2H), 10.7 (s, 1H, SH), 3.9(s, 3H, OCH3), 8.6 (s, 1H,
CHN); MS: m/z 483 [M]+; Anal. Calcd. For (C25H17N5O4S) %: C, 62.10;
H, 3.54; N, 14.48. Found: C, 62.12; H, 3.58; N, 14.44.
7-Chloro-3-{[(7-chloro-2-mercaptoquinolin-3-
yl)methylene]amino}-2-phenylquinazolin-4(3H)-one (7d)
Yield 68%, m.p. 168◦C; IR (KBr) cm−1; 3015(C H, Ar-H); 1625 (C N),
1730 (C O), 700 (C-Cl), 1300 (C=S), 1361(C-N); 1H NMR (DMSO d6), δ
7.1–7.9 (m, 8H, Ar-H), 6.9 (s, 4H, H-4),10.2 (s, 1H, SH), 8.5 (s, 1H, CHN);
MS: m/z 477 [M]+; Anal. Calcd. For (C24H14Cl2N4OS) %: C, 60.38; H,
2.96; N, 11.74. Found: C, 60.39; H, 2.91; N, 11.75.
3-{[(2-Selenooquinolin-3-yl)methylene]amino}-2-
phenylquinazolin-4(3H)-one (8a)
Yield 68%, m.p. 171◦C; IR (KBr) cm−1 ; 3019 (C H, Ar-H); 1602
(C N), 1720 (C O), 1345 (C-N); 1H NMR (DMSO d6) δ 7.0–8.1 (m, 14H,
Ar-H), 11.1 (s, 1H, SeH), 8.7 (s, 1H, CHN); MS: m/z 455 [M]+; Anal.
Calcd. For (C24H16N4OSe) %: C, 63.30; H, 3.54; N, 12.30. Found: C,
63.33; H, 3.51; N, 12.35.

468
H. R. P. Naik et al.
3-{[(2-Seleno-7-methoxyquinolin-3-yl)methylene]amino}-7-
methyl-2-phenylquinazolin-4(3H)-one (8b)
Yield 55%, m.p. 197◦C; IR (KBr) cm−1; 3018(C H, Ar-H); 1625 (C N),
1679 (C O), 1300 (C-N); 1H NMR (DMSO d6), δ 7.–8.0 (m, 12H, Ar-H),
3.81 (s, 3H, OCH3), 11.4 (s, 1H, SeH), 2.2 (s, 3H, CH3), 8.5 (s, 1H,
CHN); MS: m/z 499 [M]+; Anal. Calcd. For (C26H20N4O2Se) %: C, 62.53;
H, 4.04; N, 11.22. Found: C, 62.49; H, 4.10; N, 11.29.
3-{[(2-Seleno-7-methoxyquinolin-3-yl)methylene]amino}-7-
nitro-2-phenylquinazolin-4(3H)-one (8c)
Yield 58%, m.p. 191◦C; IR (KBr) cm−1; 3023(C H, Ar-H); 1615 (C N),
1699 (C O), 1325 (C-N), 1391 (NO2); 1H NMR (DMSO d6), δ 7.0–8.1 (m,
10H, Ar-H), 8.4 (s, 2H), 11.7 (s, 1H, SeH), 3.9(s, 3H, OCH3), 8.8 (s, 1H,
CHN); MS: m/z 530 [M]+; Anal. Calcd. For (C25H17N5O4Se) %: C, 56.61;
H, 3.23; N, 13.20. Found: C, 56.57; H, 3.29; N,13.25.
7-Chloro-3-{[(7-chloro-2-seleenoquinolin-3-
yl)methylene]amino}-2-phenylquinazolin-4(3H)-one (8d)
Yield 58%, m.p. 183◦C; IR (KBr) cm−1; 3011(C H, Ar-H); 1621 (C N),
1
1733 (C O), 709 (C-Cl), 1308 (C=S), 1368(C-N); H NMR (DMSO d6),
δ 7.2–8.0 (m, 8H, Ar-H), 6.9 (s, 4H, H-4),11.2 (s, 1H, SeH),8.5 (s, 1H,
CHN); MS: m/z 524 [M]+; Anal. Calcd. For (C24H14Cl2N4OSe) %: C,
54.98; H, 2.69; N, 10.69. Found: C, 54.91; H, 2.73; N, 10.61.
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