New syntheses of selenolo(2,3-b)quinoline-2-carboxylic ethyl esters

Article abstract of DOI:10.1080/10426500600776045

The compounds selenolo(2, 3-b)quinoline-2-carboxylic ethyl esters were synthesized in varying yields by the reaction of (i) 3-(2-chloro-3-quinolyl) acrylic acids, (ii) 3-(2-chloro-3-quinolyl)acryloyl chlorides, and (iii) 2-chloro-3-(1,2-dibromo-3-quinolyl)acrylic ethyl esters with sodium diselenide in ethanol under a nitrogen atmosphere. Copyright Taylor & Francis Group, LLC.

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Phosphorus, Sulfur, and Silicon
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New Syntheses of Selenolo(2,3-
b)quinoline-2-carboxylic Ethyl
Esters
V. Nithyadevi a & S. P. Rajendran a
a Department of Chemistry , Bharathiar University ,
TamilNadu, India
Published online: 01 Feb 2007.
To cite this article: V. Nithyadevi & S. P. Rajendran (2006) New Syntheses of
Selenolo(2,3-b)quinoline-2-carboxylic Ethyl Esters, Phosphorus, Sulfur, and Silicon and
the Related Elements, 181:11, 2623-2634, DOI: 10.1080/10426500600776045
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Phosphorus, Sulfur, and Silicon, 181:2623–2634, 2006
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500600776045
New Syntheses of Selenolo(2,3-b)quinoline-2-carboxylic
Ethyl Esters
V. Nithyadevi
S. P. Rajendran
Department of Chemistry, Bharathiar University, TamilNadu, India
The compounds selenolo(2, 3-b)quinoline-2-carboxylic ethyl esters were synthe-
sized in varying yields by the reaction of (i) 3-(2-chloro-3-quinolyl)acrylic acids,
(ii) 3-(2-chloro-3-quinolyl)acryloyl chlorides, and (iii) 2-chloro-3-(1,2-dibromo-3-
quinolyl)acrylic ethyl esters with sodium diselenide in ethanol under a nitrogen
atmosphere.
Keywords Bromination; chlorination; condensation; cyclization using sodium dise-
lenide; dehydroxychlorination; esterification; hydrolysis; Vilsmeier–Haack reaction
INTRODUCTION
Recent advances in the area of organoselenium chemistry have been
driven by the potential applications of selenium compounds in mod-
ern organic synthesis,1 biochemistry,2 photography,3 as precursors for
metal organic chemical vapor deposition of semiconducting materials,4
ligand chemistry,5 enzyme mimics, etc. In addition to these applica-
tions, some of the organic selenium compounds have been tested as
antibacterial, antiviral, antifungal, antiparasitic, antiradiation, antiin-
flammatory, antihistamine, and anticancer agents.6 Some of them also
have hypnotic, analgesic, and anesthetic effects. Selenium analogs of
phenothiazines (promazines) have a comparable action as tranquilizing
agents.6 Benzo[b]selenien-3-ylacetic acid displays auxin-like7 activity
similar to indole-3-acetic acid. The role of organoselenium compounds
prompted us to explore simpler methods to synthesize selenium ana-
logues from the appropriately functionalized quinoline systems.
Received April 13, 2005; accepted April 13, 2006.
We wish to thank Bharathiar University for the award of URF to V. Nithyadevi. We
also thank the services rendered by the Department of Chemistry, Bharathiar University
at Coimbatore; IICT at Hyderabad, and Sophisticated Instumentation facility at IISc
Bangalore, for recording elemental analysis, Proton NMR, IR and mass spectra.
Address correspondence to S. P. Rajendran, Bharathiar University, Department of
Chemistry, Coimbatore, TamilNadu 641046, India. E-mail: rajendransp@yahoo.com
2623

2624
V. Nithyadevi and S. P. Rajendran
Early workers from our laboratory have synthesized selenolo
(2,3-b)quinolines8−10 using 2-quinolone-3-ethanols and 2-chloro-3-vinyl
quinolines as the starting compounds.
We recently reported a new synthesis of selenolo(2,3-b)quinoline-2-
carboxylic ethyl esters11 in good yields by the reaction of 3-(2-chloro-
3-quinolyl)acrylic ethyl esters, with sodium diselenide in an ethanol
medium under a nitrogen atmosphere.
As part of our current studies on the development of new routes to
the synthesis of selenium heterocycles, we now report the reaction of
the following intermediates with sodium diselenide individually:
1. 3-(2-chloro-3-quinolyl)acrylic acids,
2. 3-(2-chloro-3-quinolyl)acryloyl chlorides, and
3. 2-chloro-3-(1,2-dibromo-3-quinolyl)acrylic ethyl esters.
RESULTS AND DISCUSSION
The role of Na2Se122 is excellent where it is used for the introduction
of selenium into organic molecules. An ethanolic solution of sodium
diselenide is advantageous in that it provides a superior solvent for
nucleophilic displacement reactions in water-insoluble or hydrolysis-
sensitive organic compounds.
Shanmugam et al.13−15 from our laboratory were the first to syn-
thesize selenolo(2,3-b)quinolines utilizing 2-quinolone-3-ethanols and
2-chloro-3-vinyl quinolines as starting compounds. However, the prepa-
ration of these reported precursors involved tedious procedures.
Herein, we report simple and convenient methods to synthesize
selenolo(2,3-b)quinolines from the readily accessible precursors 2-
chloro-3-formyl quinoline and its derivatives (Scheme 1).
2-chloro-3-formyl quinolines were in turn prepared by reacting ac-
etanilides with Vilsmeir reagent (POCl3/DMF).16 This pocedure in-
volves the conversion of acetanilides into 2-chloro-3-formyl quinolines
using a Vilsmeier reagent.
2-chloro-3-formyl quinolines (1) were converted to the oxo compounds
(2) by refluxing with 4M of HCl. These were then treated with mal-
onic acid, pyridine, and piperidine to furnish 3-(2-oxo-1, 2-dihydro-3-
quinolyl)acrylic acids17 (3).
(i). Compound (4a) was synthesized by the dehydroxychlorination of
3-(2-oxo-1,2-dihydro-3-quinolyl)acrylic acid (3a) with freshly distilled
phosphorus oxychloride. The structure of the resulting compound was
attested through the following spectral values.
The IR spectrum of the solid displayed bands for ( C O) at
1
1690 cm−1, ( C Cl ) at 1010 cm−1, and ( OH) at 3401 cm−1. Its H

Selenolo Carboxylic Ethyl Esters
2625
(a) R1 R2 R3 H, (b) R1 CH3, R2 R3 H, (c) R1 R3 H, R2 CH3, (d) R1 R2 H,
R3 CH3, (e) R1 OCH3, R2 R3 H, (f) R1 R3 H, R2 OCH3, (g) R1 R2 H,
R3 OCH3, (h) R1 R3 CH3, R2 H, (i) R1 H, R2 R3
CH CH CH CH .
SCHEME 1 (i) 4M HCl (ii) Malonic acid, pyridine, piperidine.
NMR spectra showed a singlet at 8.38 δ for C4 H; COOH peak at
12.95δ; doublets for vinyl protons at 6.54δ, 8.09δ with J = 16Hz typical
of a trans configuration; and a multiplet for C5, C6, C7, and C8 H at
7.63δ–7.84 δppm. Its mass spectra with the m/e value at 233(M+) and
235(M+2) (one third the intensity of the parent peak); the elemental
analysis (C, 61.71; H, 3.11; N, 5.67%) corroborated with the molecu-
lar formula C12H8ClNO2. Thus, the structure of (4a) was confirmed as
3-(2-chloro-3-quinolyl)acrylic acid (4a) (Scheme 2).
(4a) was then refluxed with sodium diselenide to give rise to the
expected product, selenolo(2,3-b)quinoline-2-carboxylic acid (9).
The resulting yellow-colored crystals exhibited IR absorption bands
at 1726 cm−1 and 1191 cm−1 characteristic of ( C O), and ( C O) of
ester with the disappearance of an acid peak at 1690 cm−1, ( OH) peak
at 3401 cm−1, and ( C Cl ) at 1010 cm−1
.
The 1H NMR spectrum of the product exhibited multiplet for 6 pro-
tons at 7.28–8.01δ(C3, C4, C5, C6, C7, C8 H), a 2-proton quartet at
4.30δ(J = 7Hz, −OCH2) and a 3-proton triplet at 1.40δ (J = 7Hz, −CH3
of ester).
The NMR data clearly showed the disappearance of CH CH and
COOH groups. The mass spectrum of the product showed the molecu-
lar ion peak at m/z = 304. The elemental analysis (C, 54.95; H, 3.32; N,
4.49%) agreed with the molecular formula C14H11NO2 Se attesting the
structure of the product as selenolo(2,3-b)quinoline-2-carboxylic ethyl
ester (8a), thus attesting the esterification of the acid group.
(ii). The next intermediate compound (5a) was synthesized by reflux-
ing 3-(2-chloro-3-quinolyl)acrylic acid (4a) with thionyl chloride. The
structure of the recrystallized product was identified on the basis of the
following spectral and analytical data.
In IR spectrum COCl peak appeared at 1780 cm−1
;
C Cl at
1020 cm−1
.
In the 1H NMR spectrum, the doublets appeared at 6.78δ (J = 16Hz,
CH CH ) and 8.23δ (J = 16Hz, CH CH ); and multiplets appeared

2626
V. Nithyadevi and S. P. Rajendran
(a) R1 R2 R3 H, (b) R1 CH3, R2 R3 H, (c) R1 R3
H , R2 CH3,
(d) R1 R2 H, R3 CH3, (e) R1 OCH3, R2 R3 H, (f) R1 R3 H,
R2 OCH3, (g) R1 R2 H, R3 OCH3, (h) R1 R3 CH3, R2 H, (i) R1 H,
R2 R3
CH CH CH CH .
SCHEME 2
at 7.59–7.92δ for C5, C6, C7, and C8 H; and a singlet appeared at 8.48δ
(C4 H).
In mass spectrum, the molecular ion peak appeared at m/e 252(M+),
254(M+2), and 256(M+4).
The elemental analysis (C, 56.91; H, 2.65; N, 5.23%) was compatible
with the molecular formula C12H7Cl2NO, attesting the structure as 3-
(2-chloro-3-quinolyl)acryloyl chloride (5a) (Scheme 2).
SCHEME 3

Selenolo Carboxylic Ethyl Esters
2627
SCHEME 4
To a freshly prepared solution of sodium diselenide in abs. ethanol, 3-
(2-chloro-3-quinolyl)acryloyl chloride (5a) was added and refluxed. The
pasty mass of the first product was left as an unidentified one.
The spectral and analytical data of the second product is given below.
IR absorption bands of the solid displayed bands at 1726 cm−1 and
1192 cm−1, with the disappearance of COCl peak at 1780 cm−1 and
C Cl at 1020 cm−1
.
Multiplet at 7.28–8.01δ (m, 6H, C3, C4, C5, C6, C7, C8 H), 2 pro-
ton quartet at 4.30δ (J = 7Hz, OCH2), and 3 proton triplet at 1.40 δ
(J = 7Hz, CH3 of ester) in the 1H NMR spectrum. The molecular
ion peak at m/z 304, with the elemental analysis (C, 54.95; H, 3.42; N
4.31%) corroborated with the molecular formula C14H11NO2Se, finally
confirming the structure as selenolo(2,3-b)quinoline-2-carboxylic ethyl
ester (8a) (Scheme 2).
(iii). To synthesize the trihalo intermediate, 3-(2-chloro-3-
quinolyl)acrylic ethyl ester (6a) was brominated with anhydrous
TABLE I The Physical and IR Data of 4a–i
Compound Yield (%)
M.P. (◦C)
IR (cm−1
)
Mass m/e
4a
4b
4c
4d
4e
4f
4g
4h
4i
72
68
68
79
79
69
60
58
64
188–189
192–193
108–109
207–208
222–223
231–232
198–199
170–171
260–261
1690, 3401, 1010
1692, 3400, 1020
1689, 3392, 1012
1695, 3393, 1015
1698, 3405, 1021
1698, 3401, 1025
1695, 3400, 1021
1678, 3375, 1010
1701, 3415, 1032
233, 235
247, 249
247, 249
247, 249
263, 265
263, 265
263, 265
261, 263
283, 285

2628
V. Nithyadevi and S. P. Rajendran
TABLE II The Physical and IR Data of 5a–i∗
Compound
Yield (%)
M.P. (◦C)
IR (cm−1
)
5a
5b
5c
5d
5e
5f
5g
5h
5i
75
78
80
82
70
71
60
60
73
150–151
161–162
120–121
174–175
182–183
190–191
169–170
194–195
201–202
1780, 1020
1780, 1020
1783, 1025
1775, 1015
1786, 1023
1790, 1029
1790, 1027
1790, 1029
1790, 1029
∗Recrystallized from chloroform.
chloroform. The structure of the resulting compound was established
from the following spectral and analytical data.
IR (KBr, cm−1) = 1721 ( C O), 1064( C Cl).
1H-NMR(CDCl3)δ ppm = 1.34(J = 7Hz, CH3 of ester), a 2 proton
quartet at 4.25(J = 7Hz, CH2 of ester), multiplet at 7.43–7.92 (4H, C5
to C8 H), 5.02(s, 2H, CHBr CHBr ), 8.25(s, C4 H).
The mass spectrum showed its molecular ion peak at 421(M+),
423(M+2), 425(M+4), and 427(M+6). The elemental analysis (C, 39.52;
H, 2.61; N, 3.19%) was compatible with the molecular formula
C14H12Br2ClNO2 confirming the structure of the compound as 2-chloro-
3-(1,2-dibromo-3-quinolyl)acrylic ethyl ester (6a) (Scheme 2).
The reaction of 2-chloro-3-(1,2-dibromo-3-quinolyl)acrylic ethyl es-
ter (6a) with sodium diselenide under a reflux temperature furnished
yellow needle-shaped crystals.
TABLE III The Physical and IR Data of 7a–i∗
Compound
Yield (%)
M.P. (◦C)
IR (cm−1
)
7a
7b
7c
7d
7e
7f
7g
7h
7i
75
70
72
72
70
71
68
70
74
151–152
174–175
125–126
155–156
105–106
140–141
137–138
164–165
182–183
1721, 1064
1720, 1060
1720, 1060
1715, 1057
1726, 1067
1730, 1069
1733, 1071
1715, 1041
1735, 1075
∗Recrystallized from pet. ether:benzene (4:1v/v).

Selenolo Carboxylic Ethyl Esters
2629
It exhibited the following spectral and analytical data: an appearance
of a peak at 1726 cm−1 and 1191 cm−1 in IR spectrum, a triplet at 1.40δ
(J = 7Hz, CH3 of ester), a quartet at 4.30δ (J = 7Hz, 2H, OCH2), and
a multiplet at 7.28–8.01δ (m, 6H, C3, C4, C5, C6, C7, C8 H) in 1H NMR
spectrum.
A molecular ion peak at m/z 304 and elemental analysis (C, 54.91;
H, 3.51; N, 4.45%) further advocated the proposed molecular for-
mula C14H11NO2Se, augmenting the structure of the compound as
selenolo(2,3-b)quinoline-2-carboxylic ethyl ester (8a) (Scheme 2).
A series of similar compounds (8b–i) were realized from (4b–i),
(5b–i), and (7b–i) in varying yields.
EXPERIMENTAL
Melting points were determined using a Raaga melting point appara-
tus and were uncorrected. IR spectra were recorded on FTIR 8201(PC)S
spectrometer as KBr pellets, and the absorption frequencies are ex-
pressed in reciprocal centimeters (cm−1). Proton NMR spectra were
recorded on a Gemini-200MHz or on a Varian AMX 400 spectrome-
ter in CDCl3. Chemical shifts were expressed in δ(ppm) downfield from
tetramethylsilane as an internal standard. Elemental analysis was per-
formed by Perkin-Elmer model 240B CHN analyzer, and the values are
within the permissible limits ( 0.5). Mass spectra were recorded by an
EIMS technique on an Autospec mass spectrometer. Crude products
were checked by TLC and purified by column chromatography using
silica gel (60–120 mesh).
The Preparation of 3-(2-chloro-3-quinolyl)acrylic Acids (4a–i):
General Procedure
3-(2-oxo-1,2-dihydro-3-quinolyl)acrylic acid (3a–i) (1.56 g, 0.008 mole)
was refluxed with phosphoryl chloride 8 mL (excess) in an oil bath for
2–21/2 h. The mixture was then cooled and poured into crushed ice.
The separated solid was filtered , washed with water, and purified by
column chromatography over silica gel using pet. ether: ethyl acetate
(10:1) as the eluent.
The Preparation of Selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Esters (8a–i) from 3-(2-Chloro-3-quinolyl)acrylic Acids (4a–i):
General Procedure
To a freshly prepared solution of sodium diselenide [selenium powder
(1.069 g, 0.0136 mole) and sodium borohydride (0.358 g, 0.0095 mole)

2630
V. Nithyadevi and S. P. Rajendran
in abs. ethanol], 3-(2-chloro-3-quinolyl)acrylic acid (4a–i) (1 g, 0.0043
mole) was added and heated under reflux temperature for 15 h on a
steam bath. Thereafter, the solution was evaporated, and the residue
was dissolved in 50 mL of chloroform followed by washing with 70 mL
of water. The organic extract was dried and evaporated. Column chro-
matography was used to purify the crude product using pet. ether as
the eluent. The first product was left as an unidentified one since it was
a pasty mass.
The Preparation of 3-(2-Chloro-3-quinolyl)acryloyl Chloride
(5a–i): General Procedure
3-(2-chloro-3-quinolyl)acrylic acid (4a–i) (1 g, 0.043 mole) was refluxed
with thionyl chloride (1.56 mL, 0.0214 mole) for 1 h. Excess thionyl
chloride was removed by co-distillation with benzene, and the resulting
acid chloride was recrystallized from chloroform.
The Preparation of Selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Esters (8a–i) from 3-(2-Chloro-3-quinolyl)acryloyl Chloride
(5a–i): General Procedure
To a freshly prepared solution of sodium diselenide [selenium powder
(0.991 g, 0.0131 mole) and sodium borohydride (0.332 g, 0.0088 mole)
in abs. ethanol], 3-(2-chloro-3-quinolyl)acryloyl chloride (5a–i) (1 g,
0.0043 mole) was added and heated under reflux temperature for 15 h on
a steam bath. Thereafter, the solution was evaporated, and the residue
was dissolved in 40 mL of chloroform followed by washing with 70 mL
of water. The organic extract was dried and evaporated. Column chro-
matography was used to purify the crude product using pet. ether as the
eluent. The pasty mass of the first product was left as an unidentified
one. The second product was identified as selenolo(2,3-b)quinoline-2-
carboxylic ethyl ester.
The Preparation of 2-Chloro-3-(1,2-dibromo-3-quinolyl)-
acrylic Ethyl Ester (7a–i): General Procedure
Bromine (0.18 mL, 0.0036 mole) in 10 mL of anhydrous chloroform was
added in a dropwise manner to a cooled, stirred suspension of 3-(2-
chloro-3-quinolyl)acrylic ethyl ester (6a) (0.9 g, 0.0033 mole) in 20 mL
of anhydrous chloroform, for about 30 min.
Stirring and cooling was continued for another 3 h. A light brown
yellow powder resulted from distilling out the solvent together with

Selenolo Carboxylic Ethyl Esters
2631
excess bromine. It was then recrystallized from pet. ether:benzene (4:1
v/v) to yield creamy white needles.
The Preparation of Selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Esters (8a–i) from 2-Chloro-3-(1,2-dibromo-3-quinolyl)acrylic
Ethyl Ester (7a–i): General Procedure
To a freshly prepared solution of sodium diselenide [selenium powder
(0.593 g, 0.0075 mole,) and sodium borohydride (0.198 g, 0.0053 mole)
in abs. ethanol], 2-chloro-3-(1,2-dibromo-3-quinolyl)acrylic ethyl ester
(7a–i) (1 g, 0.0024 mole) was added and heated under reflux tempera-
ture for 15 h on a steam bath. Thereafter, the solution was evaporated
and the residue was dissolved in 40 mL of chloroform followed by wash-
ing with 70 mL of water. The organic extract was dried and evaporated.
The residue was then chromatographed over silicagel with pet. ether
as the eluent. The first product was left as an unidentified one since it
was a pasty mass. The second product was identified as selenolo(2,3-
b)quinoline-2-carboxylic ethyl ester.
Physical and Spectroscopic Data of (8a–i)
Selenolo(2,3-b)-quinoline-2-carboxylic Ethyl Ester (8a)
Light-yellow needle-shaped crystals, Yield = 65%, m.p. = 194–196◦C,
Lit.11 m.p. 194–196◦C (Cal: C, 55.20; H, 3.64; N, 4.62; Found: C, 55.4;
H, 3.50; N, 4.59), IR (KBr, cm−1) = 1726( C O of ester), 1192 ( C O of
ester), 1H NMR (CDCl3)δ ppm: 1.40 (t, J = 7 Hz, CH3 of ester), 4.30 (q,
J = 7 Hz, OCH2 of ester), 7.28–8.01 (m, 6H, C3, C4, C5, C6, C7, C8 H),
M F = C14H11NO2Se, Mass (m/z)M+ = 304.
6-Methyl Selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Ester (8b)
Light-yellow needle-shaped crystals, Yield = 60%, m.p. = 159–161◦C,
Lit.11 m.p. 159–161◦C (Cal: C, 56.59; H, 4.12; N, 4.42; Found: C, 56.50;
H, 4.10; N, 4.40), IR (KBr, cm−1) = 1709 (C O of ester), 1251 ( C O of
1
ester), H NMR(CDCl3) δ ppm: 1.43 (t, J = 7 Hz, CH3 of ester), 4.42
(q, J = 7 Hz, OCH2 of ester), 2.57 (s, 3H, CH3), 8.26 (s, 1H, C4 H),
8.53 (s, C3 H), 8.13 (d, J = 2 Hz, C5 H), 8.03 (s, C7 H), 7.64 (d, C8 H,
J = 8.2 Hz). M.F = C15H13NO2Se, Mass (m/z)M+ = 318.
7-Methyl Selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Ester (8c)
Light-yellow needle-shaped crystals, Yield = 66%, m.p. = 178–180◦C,
Lit.11 m.p. 178–180◦C (Cal: C, 56.59; H, 4.12; N, 4.42; Found: C, 56.60;

2632
V. Nithyadevi and S. P. Rajendran
H, 4.12; N, 4.50), IR (KBr, cm−1) = 1712 (C O of ester), 1251 ( C O of
1
ester), HNMR(CDCl3)δ ppm: 1.42 (t, J = 6.6 Hz, CH3 of ester), 4.44
(q, J = 6.8 Hz, OCH2 of ester), 2.61 (s, 3H, CH3), 8.25 (s, 1H, C4 H),
8.56 (s, C3-H) 7.39–7.92 (m, 3H, C5, C6, C8 H). M.F = C15H13NO2Se,
Mass (m/z)M+ = 318.
8-Methyl Selenolo(2,3-b)quinoline-2-carboxylic Ethyl Ester
(8d)
Light-yellow needle-shaped crystals, Yield = 75%, m.p. = 164–166◦C,
Lit.11 m.p. 164–166◦C (Cal: C, 56.59; H, 4.12; N, 4.42; Found: C, 56.60;
H, 4.12; N, 4.50), IR (KBr, cm−1) = 1724 (C O of ester), 1254 ( C O of
1
ester), H NMR(CDCl3) δ ppm: 8.25 (s, C4 H), 8.56 (s, C3 H), 7.45 (t,
J = 7.4 Hz, C6 H), 7.79 (d, J = 8 Hz, C5 H), 7.63 (d, J = 7 Hz, C7 H),
2.86 (s, 3H, CH3), 1.44 (t, J = 7 Hz, 3H, CH3 (of ester)), 4.43 (q, J =
7 Hz, 2H, OCH2). M.F = C15H13NO2Se, Mass (m/z) M+ = 318.
6-Methoxy Selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Ester (8e)
Light-yellow needle-shaped crystals, Yield = 66%, m.p. = 145–147◦C,
Lit.11 m.p. 145–147◦C (Cal: C, 53.88; H, 3.92; N, 4.21; Found: C, 53.80;
H, 3.99; N, 4.21), IR (KBr, cm−1) = 1718 ( C O of ester), 1242 ( C O
1
of ester), H NMR(CDCl3)δ ppm: 8.28 (s, C4 H), 8.54 (s, C3-H), 7.51–
7.93 (m, 3H, C5, C7, C8 H), 4.47 (q, J = 7.6 Hz, 2H, OCH2), 3.99 (s,
3H, OCH3), 1.46 (t, J = 6.4 Hz, 3H, CH3) M.F = C15H13NO3Se, Mass
(m/z)M+ = 334.
7-Methoxy Selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Ester (8f)
Light-yellow needle-shaped crystals, Yield = 58%, m.p. = 154–156◦C,
Lit.11 m.p. 154–156◦C (Cal: C, 53.88; H, 3.92; N, 4.21; Found: C, 53.89;
H, 3.99; N, 4.15), IR (KBr, cm−1) = 1700 (C O of ester), 1245 ( C O of
ester), 1H NMR(CDCl3)δ ppm: 8.23 (s, C4 H), 8.50 (s, C3 H), 7.24–7.84
(m, 3H, C5, C6, C8 H), 3.97 (s, 3H, OCH3), 1.45 (t, 3H, CH3), 4.40 (q,
J = 6.2 Hz, OCH2) M.F = C15H13NO3Se, Mass (m/z) M+ = 334.
8-Methoxy-selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Ester (8g)
Light-yellow needle-shaped crystals, Yield = 49%, m.p. = 161–
162◦C, (Cal: C, 53.88; H, 3.92; N, 4.21; Found: C, 53.89; H, 3.99; N,
1
4.15), IR(KBr, cm−1) = 1720(C O of ester), 1241 ( C O of ester), H
NMR(CDCl3)δppm: 8.30(s, C4 H), 8.54(s, C3 H), 7.28–7.91(m, 3H, C5,

Selenolo Carboxylic Ethyl Esters
2633
C6, C7 H), 4.01(s, 3H, OCH3), 1.47(t, 3H, CH3), 4.48(q, J = 6.2 Hz,
OCH2). M.F = C15H13NO3Se, Mass (m/z) M+ = 334.
6,8-Dimethyl-selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Ester (8h)
Light-yellow-needle-shaped crystals, Yield = 56%, m.p. = 184–
185◦C, (Cal: C, 57.84; H, 4.55; N, 4.22; Found: C, 57.56; H, 4.25; N,
4.02), IR (KBr, cm−1) = 1709 (C O of ester), 1219 ( C O of ester), 1H
NMR(CDCl3)δ ppm: 2.40, 2.55 (seach
,
CH3), 8.18 (s, C4 H), 8.48 (s,
C3 H), 7.20 (s, C7 H), 7.41 (s, C5 H), 1.39 (t, 3H, CH3), 4.41 (q, J =
6.2 Hz, OCH2). M.F = C16H15NO2Se, Mass (m/z)M+ = 332.
Benzo(h) Selenolo(2,3-b)quinoline-2-carboxylic Ethyl
Ester (8i)
Light-yellow needle-shaped crystals, Yield = 60%, m.p. = 191–
192◦C, (Cal: C, 61.03; H, 3.70; N, 3.95; Found: C, 60.92; H, 3.35; N,
1
3.51), IR (KBr, cm−1) = 1735(C O of ester), 1246 ( C O of ester), H
NMR(CDCl3)δ ppm: 1.52(t, J = 7.2 Hz, CH3 of ester), 4.48 (q, J =
7.2 Hz, OCH2 of ester), 7.49–9.51 (m, 8H, C3, C4, C5, C6, C7, C8, C9,
C10 H). M.F = C18H13NO2Se, Mass (m/z) M+ = 354
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