An efficient route for synthesis and reactions of seleno[2, 3-c]coumarin

Article abstract of DOI:10.3987/COM-16-13445

Synthesis of new selenium-containing coumarin moiety via the reaction of 4-chloro-2-oxo-2H-chromene-3-carbonitrile with selenium and sodium borohydride gave 3-cyano-4-coumarinselenol which reacted with different halo-acids, such as chloroacetonitrile, eth

Full text of DOI:10.3987/COM-16-13445

HETEROCYCLES, Vol. 92, No. 6, 2016, pp. -. © 2016 The Japan Institute of Heterocyclic Chemistry
Received, 24th February, 2016, Accepted, 29th March, 2016, Published online, 14th April, 2016
DOI: 10.3987/COM-16-13445
AN EFFICIENT ROUTE FOR SYNTHESIS AND REACTIONS OF
SELENO[2, 3-c]COUMARIN
Shams H. Abdel-Hafez,*a,b Ahmed Elkhateeb,a,c Adel A. Gobouri,a Islam H. El
Azab,a,d and Gilbert Kirsche
a
Chemistry Department, Faculty of Science, Taif University, Taif 21974, Saudi
Arabia
b
Chemistry Department, Faculty of Science, Chemistry department, Taif
University, Taif Kingdom Saudi arabia; E-mail: shams@aun.edu.eg;
shams_abdelhafez@yahoo.com
c
Phytochemistry and plant systematic department, National Research Centre,
Dokki 12622 Giza, Egypt
d
Chemistry Department, Faculty of Science, Aswan University, Aswan, 81528
Egypt
e UMR 7565 SRSMC, Boulevard Arago, 57070 Metz, France
Abstract — Synthesis of new selenium-containing coumarin moiety via the
reaction of 4-chloro-2-oxo-2H-chromene-3-carbonitrile with selenium and sodium
borohydride gave 3-cyano-4-coumarinselenol which reacted with different
halo-acids, such as chloroacetonitrile, ethyl chloroacetate and chloroacetamide to
give the corresponding 3-amino-4-oxo-4H-seleno[3,2-c]chromene derivatives.
Hydrazonolysis of the obtained new ethyl 3-amino-4-oxo-4H-seleno[3,2-c]-
hyphen chromene-2-carboxylate afforded the corresponding hydrazino compound.
The hydrazino compound was used as a versatile precursor for synthesis of new
other heterocyclic compounds containing selenocoumarin moiety. The newly
1
synthesized compounds were characterized using the spectroscopic tools (IR, H
NMR, 13C NMR and mass spectroscopy) as well as microanalysis.
INTRODUCTION
Coumarins natural and synthetic have been found to exhibit a variety of pharmacological activities like
anti-HIV,1 anticoagulant,2 antibacterial,3 antioxidant,4 and anti-inflammatory.5 Among the diverse

biological activities of coumarin the most intriguing bioactivity is the effect against breast cancer. 6-9 On the
other hand, in last years, many kinds of selenophene derivatives have been increased remarkably in organic
synthesis due to their chemical properties and biological activities.10-18 For example a series of selenophene
derivativies are reported as potent inhibitors CHK1 kinase.19 Therefore, many medicinal preparations have
been produced on the basis of organic derivatives of selenophene. In continuation of our program on
selenium containing heterocyclic systems,14-18 here in this paper we discuss the synthesis of selenophene
based on coumarin moiety to discover new useful compounds for the treatment of many diseases and act as
antioxidant and anti-inflammatory agents with significant analgesic effect.
RESULTS AND DISCUSSION
To achieve our target compounds, we started from compound, 4-hydroxycoumarin (1), which undergoes
Vilsmeier formylation onto 4-chloro-3-formylcoumarin (2). Compound 2 showed different reactivity
depending on the reaction conditions. Its reaction with hydroxylamine gives a variety of products which
described before in the last our paper.20 The obtained products were 4-chloro-3-cyanocoumarin (4);
4H-coumarino[3,4-d]isoxazol-4-one (5); ethyl 5-(2-hydroxyphenyl)isoxazole-4-formate (6) via the
intermediate compound (3) (Scheme 1).
Cl
CHO
OH
O
O
N
Cl
Cl
4
O
CHO
NH2OH.HCl
POCl3/ DMF
NOH
O
O
O
O
O
O
O
O
1
2
3
5
N
OH
O
Scheme 1
6
CO2Et
Those compounds were separated in good yields by preparative TLC. Chlorocyanocoumarin 4 was used as
a versatile precursor for synthesis of new 3-cyano-4-coumarinselenol (7) by refluxing with selenium metal
and sodium borohydride in ethanol. Compound 7 was characterized by 1H NMR spectrum which showed
singlet peak at (δ, ppm): 14.02 due to (-SeH). Compound 7 reacted with different halo-acids such as
chloroacetonitrile or ethyl chloroacetate or chloroacetamide in DMF and excess of NaOH underwent
Thorpe-Ziegler cyclization to afford the corresponding compounds selenochromene carbonitrile (8),
selenochromenecarboxylate (9) and selenochromenecarboximide (10) derivatives (Scheme 2). All the
newly synthesized compounds 2-10 were confirmed by IR, 1H NMR, 13C NMR and mass spectroscopy as
well as microanalysis.

CN
Se
NH2
ClCH2CN
O
O
CO2Et
NH2
SeH
O
8
Se
ClCH2CO2Et
CN
O
Se/NaBH4
EtOH
4
O
O
7
ClCH2CONH2
9
CONH2
Se
NH2
Scheme 2
O
O
10
Selenochromenecarboxylate 9 was used as a key in the synthesis of different new heterocyclic system based
on coumarin. The reactivity of the ester group in 9 was tested via its hydrazonolysis with hydrazine hydrate
which, afforded the corresponding selenochromenecarbohydrazide (11). Compound 11 would be served as
precursor of other heterocyclic compounds as follows: compound 11 was reacted with triethyl orthoformate
in ethanol in the presence of catalytic drops of acetic acid to give chromenoselenopyrimidine (12). Also,
compound 11 reacted with sodium nitrite solution in acetic acid to give the corresponding carbonylazide
derivative (13) which underwent Curtius rearrangement upon boiling in dry xylene giving
chromenoselenoimidazole derivative (14). On the other hand condensation of carbohydrazide 11 with
acetylacetone in ethanol afforded pyrazolylselenochromen derivative (15) (Scheme 3).
H
N
O
Se
NH
9
OEt
O
O
14
NH2NH2/EtOH
N
O
Xylene
N
CONHNH2
CON3
Se
Se
Se
N
CH(OEt)3/AcOH
NH2
NH2
NaNO2/AcOH
O
O
O
O
O
12
O
O
11
13
O
O
N
Me
N
Se
NH2
Me
O
O
15
Scheme 3

Finally, the reaction of selenochromenecarboxylate 9 with alcoholic sodium hydroxide under reflux
afforded 3-amino-4-oxo-4H-seleno[3,2-c]chromene-2-carboxylic acid (16) which reacted with acetic
anhydride under reflux to give 8-methyl-6,10-dihydro-chromeno[3',4':4,5]seleno[3,2-d][1,3]-
oxazine-6,10-dione (17). Refluxing of compound 17 with aniline gave 8-methyl-6,10-dihydro-7(6H)-
chromeno[3',4':4,5]seleno[3,2-d]pyrimidine-6,10-dione (18) (Scheme 4).
CO2Et
CO2H
Se
Se
NH2
NH2
NaOH/EtOH
O
O
O
O
9
16
Ac2O
Ph
O
O
O
N
Se
Se
Me
N
Me
N
PhNH2
O
O
O
O
17
18
Scheme 4
Chemical structures of all products obtained 11-18 were confirmed by IR and NMR spectroscopy, mass
spectrometry and elemental microanalysis.
EXPERIMENTAL
General Methods. The melting points were determined by using the Kofler melting point apparatus, and
were uncorrected. IR (KBr, cm-1) spectra were recorded on a Pye-Unicam SP3–100 instrument at Taif
1
University. H NMR spectra were obtained on a Varian (400 MHz) EM 390 USA instrument at King
13
Abdel-Aziz University. C NMR spectra were recorded on a JNM-LA spectrometer (100 MHz) at King
Abdel-Aziz University, Saudi Arabia. For both 1H and 13C NMR, DMSO-d6 or (CDCL3) was used. Spectra
were internally referenced to TMS. Peaks are reported in ppm downfield of TMS. Multiplicities are
reported as singlet (s), doublet (d), triplet (t), quartet (q). Mass spectra were recorded on ISQ Thermo
Scientific GC-MS. GC column TG-SQC, Trace GC ultra at Taif University KSA for compounds 2-6. Purity
of the compounds was checked by thin layer chromatography (TLC) using silica gel plates.
Note: Compounds 7-18 were determined by using EI-MS on JEOL-JMS-AX 500 at Cairo National
Research Center Cairo, Egypt.

4-Chloro-3-coumarincarbaldehyde (2). Compound 2 was prepared as previously describe by Sabitae et
al. with a little modification.20-21 The pale yellow solid was collected by filtration and recrystallized from
acetone to give 10.5 g (84%) of 2; mp 133-135 °C (lit. 130 °C).20 1H NMR (DMSO-d6) δ, ppm: 10.39 (1H,
s, CH=O), 8.16–7.28 (4H, m, Ar-H); IR ν 1720 (C=O-pyrone), 1663 (CHO) cm–1. EI-MS m/z: 208 (M+, 11),
182 (31), 180 (100), 154 (31), 152 (91), 124 (20), 101 (11), 89 (80), 63 (37), 62 (31), 61 (14); EI-HRMS:
m/z 207.9909 (calculated for C10H5ClO3 207.9927)
3-Cyano-4-chlorocoumarin (4), 4H-chromeno[3,4-d]isoxazol-4-one (5), ethyl 5-(2-hydroxyphenyl)-
isoxazole-4-carboxylate (6): were prepared as previously described.20
Compound 4 as yellow crystal mp 198-200 °C (Lit, 199-200 °C).22
1
4H-Chromeno[3,4-d]isoxazol-4-one (5), mp 222-224 °C; H NMR (DMSO-d6) δ, ppm: 10.21 (1H, s,
13
CH-isoxazole), 8.03–7.41 (4H, m, Ar-H); C NMR δ, ppm: 165.50, 155.04, 154.90, 152.80, 133.36,
125.29, 124.07, 117.67, 110.24, 107.83. IR ν 1761 (C=O-pyrone), 1608 (C=N) cm–1. EI-MS m/z: 187 (M+,
100), 159 (33), 131 (11), 119(4), 103 (54), 76 (26). EI-HRMS: m/z 187.0268 (calculated for C10H5NO3:
187.0269)
Ethyl 5-(2-hydroxyphenyl)isoxazole-4-formate (6), mp 218-220 °C; 1H NMR (CDCl3) δ, ppm: 9.02 (1H,
s, CH-isoxazole), 8.12–7.01 (4H, m, Ar-H), 4.37 (2H, q, J= 6.80 Hz, CH2); 1.36 (3H, t, J= 6.80 Hz,
CH3).13C NMR δ, ppm: 175.80, 163.49, 160.60, 155.68, 134.01, 125.66, 122.80, 118.68, 116.20.93.54,
60.29, 13.72.IR ν 1669 (C=O…H-bond), 1601 (C=N) cm–1. EI-MS m/z 233 (M+, 33), 187 (100), 159 (41),
131 (12), 119 (4), 103 (35), 76 (8); EI-HRMS: m/z 233.0684 (calculated for C12H11NO4: 233.0688).
3-Cyano-4-coumarinselenol (7).
A mixture of compound 4 (2.05 g, 0.01 mol), selenium powder (1g, 0.12 mol) and NaBH4 (1.2 g, 0.031
mol) were refluxed in 50 mL of EtOH for 3 h, and then the reaction mixture cooled and poured onto 50 mL
crushed ice/HCl. The precipitated compound was collected, dried and recrystallized from EtOH as orange
1
precipitate in 85% yield, mp 218-220 °C. IR: 2223 (CN), 1719 (C=O chromene) cm–1. H NMR
(DMSO-d6) δ, ppm: 14.02 (s, 1H, SeH), 7.20–7.80 (4H, m, Ar-H). 13C NMR δ, ppm: 160.1, 155.4, 128.3,
127.8, 126.8, 125.4, 119.9, 104.8, 100.4, 115.3. Mass: m/z: 251 [M+ + 1, 27%]. Anal. Calcd for
C10H5NO2Se (250.11): C, 48.02; H, 2.01; N, 5.60%. Found: C, 47.99; H, 2.00; N, 5.55%.
3-Amino-4-oxo-4H-seleno[3,2-c]chromene-2-carbonitrile (8), Ethyl 3-amino-4-oxo-4H-seleno[3,2-c]-
chromene-2-carboxylate (9), 3-Amino-4-oxo-4H-seleno[3,2-c]chromene-2-carboximide (10)
General procedure:
A mixture of seleno compound (7) (2.51 g, 0.01 mol) and halo compounds (chloroacetonitrile or ethyl
chloroacetate or chloroacetamide) (0.012 mol) was dissolved in DMF (30 mL) containing aq. KOH (10%, 5
mL). The reaction mixture was stirred for 1 h., after that another KOH solution (5 mL) was added and

stirred for another 1 h. The precipitate product that formed was collected, dried and recrystallized from
EtOH affording compounds 8-10 respectively.
3-Amino-4-oxo-4H-seleno[3,2-c]chromene-2-carbonitrile (8), as a yellow crystal in 85% yield, mp 275–
277 °C; IR: 3460, 3350 (NH2), 1725 (C=O chromene), 2217 (CN) cm–1. 1H NMR (DMSO-d6): δ, ppm: 6.90
(2H, s, NH2), 7.20–7.80 (4H, m, Ar-H). ). 13C NMR δ, ppm: 175.1, 160.1, 155.4, 128.3, 127.8, 126.8, 125.4,
119.9, 139.1, 131.5, 113.9, 75.3. Mass: m/z: 289 [M+, 20%]. Anal. Calcd for C12H6N2O2Se (289.15): C,
49.85; H, 2.09; N, 9.69%. Found: C, 49.68; H, 2.00; N, 9.54%.
Ethyl 3-amino-4-oxo-4H-seleno[3,2-c]chromene-2-carboxylate (9), as a yellow crystal in 88% yield, mp
200–202 °C; IR: 3470, 3367 (NH2), 1725 (C=O chromene), 1695 (C=O ester) cm-1. 1H NMR (CDCl3): δ,
ppm: 1.35–1.40 (3H, J = 7.0 Hz, t, CH3), 4.30–4.50 (2H, J = 6.0 Hz, q, CH2), 7.19 (2H, s, NH2), 7.20–7.80
13
(4H, m, Ar-H). C NMR δ, ppm: 166.9, 165.4, 160.1, 155.4, 139.7, 131.5, 128.3, 127.8, 126.8, 125.4,
119.9, 95.6, 63.1, 14.8. Mass: m/z: 337 [M+ + 1, 100%]. Anal. Calcd for C14H11NO4Se (336.20): C, 50.01;
H, 3.30; N, 4.17%. Found: C, 49.88; H, 3.25; N, 4.01%.
3-Amino-4-oxo-4H-seleno[3,2-c]chromene-2-carboximide (10), as an orange crystal in 80% yield, mp
1
280–282 °C; IR: 3500, 3460, 3350, 3250 (2NH2), 1725 (C=O chromene), 1660 (C=O) cm–1. H NMR
13
(DMSO-d6): δ, ppm: 7.19 (2H, s, NH2), 5.90 (2H, s, NH2); 7.20–7.80 (4H, m, Ar-H). C NMR δ, ppm:
168.3, 164.3, 160.1, 155.4, 139.0, 131.0, 128.3, 127.8, 126.8, 125.4, 119.9, 97.5. Mass: m/z: 307 [M+, 20%].
Anal. Calcd for C12H8N2O3Se (307.16): C, 46.92; H, 2.63; N, 9.12%. Found: C, 46.76; H, 2.55; N, 9.00%.
3-Amino-4-oxo-4H-seleno[3,2-c]chromene-2-carbohydrazide (11).
A mixture of compound (9) (3.36 g, 0.01 mol) and hydrazine hydrate (3 mL, 0.06 mol) was refluxed for 1 h
then absolute EtOH (20 mL) was added. The reaction mixture was refluxed for additional 2 h. The
precipitated product which formed was dried and recrystallized from EtOH to give pale yellow crystals in
66% yield, mp 270–272 °C. IR: 3450, 3350, 3180 (NH, NH2), 1725 (C=O chromene), 1650 (CONH) cm-1.
1H NMR (DMSO-d6): δ, ppm: 4.45 (2H, s, NH2), 6.90 (2H, s, NH2), 7.20–7.50 (4H, m, Ar-H), 8.85 (1H, s,
NH). 13C NMR δ, ppm: 166.5, 164.3, 160.1, 155.4, 139.0, 131.0, 128.3, 127.8, 126.8, 125.4, 119.9, 97.5.
Mass: m/z 322 [M+, 30%]. Anal. Calcd for C12H9N3O3Se (322.18): C, 44.74; H, 2.82; N, 13.04%. Found: C,
44.58; H, 2.77; N, 13.00%.
(E)-Ethyl N-(6,10-dioxo-6H-chromeno[3',4':4,5]seleno[3,2-d]pyrimidin-9(10H)-yl)formimidate (12).
A mixture of compound (11) (3.22 g, 0.01 mol) and triethyl orthoformate (8 mL, 0.027 mol) was refluxed in
presence of glacial acetic acid (3 mL) for 3 h. The precipitate product which formed on hot was filtered off,
dried and recrystallized from DMF/EtOH mixture giving pale yellow crystals in 55% yield, mp > 300 °C.
IR: 1720 (C=O chromene), 1660 (C=O pyrimidine) cm-1. 1H NMR (DMSO-d6): δ, ppm: 1.25–1.40 (3H, t,
CH3, J=7 Hz), 4.30–4.40 (2H, q, CH2, J=7.1 Hz); 7.60–8.50 (6H, m, Ar-H + CH-pyrimidine+ CH=N). 13 C
NMR δ, ppm: 168.0, 163.5, 160.1, 157.4, 150.8, 149.5, 139.6, 131.01, 128.3, 127.8, 126.8, 125.4, 119.9,

115.05, 63.4, 15.3. Mass: m/z 388 [M+, 25%]. Anal. Calcd for C16H11N3O4Se (388.24): C, 49.50; H, 2.86; N,
10.82%. Found: C, 49.45; H, 2.77; N, 10.59%.
3-Amino-4-oxo-4H-seleno[3,2-c]chromene-2-carbonylazide (13).
To a stirred solution of compound (11) (3.22 g, 0.01 mol) in glacial acetic acid (15 mL) sodium nitrite
solution (4.5 g, 0.07 mol) was added dropwise at 0-5 °C for 15 min, a brown precipitate was formed and
then filtered off, washed with water, dried and used without recrystallization for the following step, in 47%
yield, mp 145–147 °C. IR: 3450, 3350 (NH2), 2100 (N3), 1725 (C=O chromene), 1660 (C=O azide) cm-1.
13
1H NMR (CDCl3): δ, ppm: 7.19 (2H, s, NH2), 7.25–7.60 (4H, m, Ar-H). C NMR δ, ppm: 189.5, 172.0,
160.1, 155.4, 139.3, 131.6, 128.3, 127.8, 126.8, 125.4, 119.9, 107.01. Mass: m/z 333[M+, 30%]. Anal.
Calcd for C12H6N4O3Se (333.16): C, 43.26; H, 1.82; N, 16.82%. Found: C, 43.10; H, 1.76; N, 16.78%.
7,9-Dihydro-6H,8H-chromeno[3',4':4,5]seleno[2,3-d]imidazole-6,8-dione (14).
A mixture of 13 (1 g, 0.003 mol) in dry xylene (10 mL) was refluxed for 2 h. The solid product which
formed on hot was filtered off, washed three times by xylene, dried and recrystallized from xylene as dark
green crystals in 50% yield, mp > 300 °C. IR: 3450, 3350 (2NH), 1725 (C=O chromene), 1645 (C=O
imidazole) cm-1. 1H NMR (DMSO-d6): δ, ppm: 5.90 (2H, s, 2NH); 7.20–7.75 (4H, m, Ar-H). 13C NMR δ,
ppm: 160.1, 155.4, 151.01, 139.5, 131.08, 128.3, 127.8, 126.8, 125.4, 119.9, 118.68, 99.5. Mass: m/z 305
[M+, 50%]. Anal. Calcd for C12H6O3N2Se (305.15): C, 47.23; H, 1.98; N, 9.18%. Found: C, 47.11; H, 1.80;
N, 9.11%.
3-Amino-2-[(3,5-dimethyl-1H-pyrazol-1-yl)carbonyl]-4H-seleno[3,2-c]chromen-4-one (15).
A mixture of carbohydrazide (11) (3.22 g, 0.01 mol) and acetylacetone (1.2 mL, 0.013 mol) was refluxed in
EtOH (10 mL) for 3 h. The precipitate product was filtered off and recrystallized from EtOH as yellow
crystals in 60% yield, mp 250–252 °C. IR: 3350, 3250 (NH2), 1720 (C=O chromene), 1690 (C=O) cm-1. 1H
NMR (DMSO-d6): δ, ppm: 2.30–2.45 (6H, 2s, 2CH3), 6.90 (2H, s, 2NH2), 5.50 (1H, s, CH-pyrazole), 7.20–
7.50 (4H, m, Ar-H). 13C NMR δ, ppm: 188.8, 170.2, 164.0, 161.9, 160.1, 152.3, 155.4, 143.2, 131.7, 128.3,
127.8, 126.8, 125.4, 119.9, 105.5, 13.7, 13.2. Mass: m/z 386 [M+, 45%]. Anal. Calcd for C17H13N3O3Se
(386.26): C, 52.86; H, 3.39; N, 10.88%. Found: C, 52.66; H, 3.29; N, 10.78%.
3-Amino-4-oxo-4H-seleno[3,2-c]chromene-2-carboxylic acid (16).
A suspension of ester compound (9) (3.36 g, 0.01 mol) in 10% ethanolic sodium hydroxide (40 mL) was
heated under reflux for 3 h., and then allowed to cool. The reaction mixture was diluted with (50 mL) of
water, filtered, and then acidified with dilute acetic acid. The precipitate was filtered off and recrystallized
from dioxane to give orange crystals, yield 68%; mp 245–247 ºC. IR: 3420, 3300 (NH2), 1720 (C=O
1
chromene), 1640 (C=O) cm-1. H NMR (DMSO-d6): δ, ppm: 10.55 (1H, s, COOH); 7.20-7.75 (6H, m,
H-Ar + NH2). 13C NMR δ, ppm: 168.0, 164.4, 160.1, 155.4, 139.1, 131.8, 128.3, 127.8, 126.8, 125.4, 119.9,

93.5. Mass: m/z 309 [M+ +1, 35%]. Anal. Calcd for C12H7NO4Se (308.15): C, 46.77; H, 2.29; N, 4.55%.
Found: C, 46.55; H, 2.15; N, 4.44%.
8-Methyl-6,10-dihydrochromeno[3',4':4,5]seleno[3,2-d][1,3]oxazine-6,10-dione (17).
Compound 16 (3.08 g, 0.01 mol) in acetic anhydride (25 mL) was heated under reflux for 3 h, and allowed
to cool at room temperature. The crystalline product was collected, dried in air, and applied in the next
reaction without recrystallization, yield 35%; mp 265–267 ºC. IR: 1720 (C=O chromene), 1640 (C=O) cm-1.
1H NMR (DMSO-d6): δ, ppm: 7.20–7.55 (4H, m, H-Ar); 1.95 (3H, s, CH3). 13C NMR δ, ppm: 175.1, 164.0,
161.8, 160.1, 140.0, 134.2, 155.4, 128.3, 127.8, 126.8, 125.4, 119.9, 112.6, 16.3. Mass: m/z 333 [M+ +1,
15%]. Anal. Calcd for C14H7NO4Se (332.17): C, 50.62; H, 2.12; N, 4.22%. Found: C, 50.33; H, 2.11; N,
4.10%.
8-Methyl-6,10 dihydro-7(6H)-chromeno[3',4':4,5]seleno[3,2-d]primidine-6,10-dione (18)
A mixture of compound 17 (3.32 g, 0.01 mol) and aniline (1 mL) in glacial acetic acid (10 mL) was heated
under reflux for 3 h. The reaction mixture was cooled and diluted with water. The solid precipitate was
collected and recrystallized from an EtOH/DMF mixture to give pale yellow crystals, yield 35%; mp 235–
237 ºC. IR: 1720 (C=O chromene), 1660 (C=O) cm-1. 1H NMR (DMSO-d6): δ, ppm: 7.20-7.95 (9H, m, H
13
Ar); 2.10 (3H, s, CH3). C NMR δ, ppm: 168.1, 164.5, 160.1, 157.9, 140.1, 133.4, 155.4, 128.3, 127.8,
126.8, 125.4 (2-Ar), 119.9, 115.4, 25.8. Mass: m/z 408 [M+ +1, 65%]. Anal. Calcd for C20H12N2O3Se
(407.28): C 58.98; H 2.97; N 6.88% . Found: C 58.88; H 2.78; N 6.77%.
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