Synthesis and Characterization of Unsymmetric 4-Picolyl Selenides

Article abstract of DOI:10.1080/10426507.2015.1085041

A number of unsymmetrical heteroaryl 4-picolyl selenides have been prepared by lithiation of 4-picoline using lithium diisopropylamide under cryogenic conditions. The intermediate 4-lithiopicoline formed was then reacted with elemental selenium followed b

Full text of DOI:10.1080/10426507.2015.1085041

Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN: 1042-6507 (Print) 1563-5325 (Online) Journal homepage: http://www.tandfonline.com/loi/gpss20
Synthesis and Characterization of Unsymmetric 4-
Picolyl Selenides
Gurjeet Gujral, Shivani D. Gulati, Kuldip K. Bhasin, V. A. Potapov & S. V.
Amosova
To cite this article: Gurjeet Gujral, Shivani D. Gulati, Kuldip K. Bhasin, V. A. Potapov
& S. V. Amosova (2015): Synthesis and Characterization of Unsymmetric 4-
Picolyl Selenides, Phosphorus, Sulfur, and Silicon and the Related Elements, DOI:
10.1080/10426507.2015.1085041
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Date: 13 January 2016, At: 08:06

PHOSPHORUS, SULFUR, AND SILICON
2016, VOL. 0, NO. 0, 1–4
http://dx.doi.org/10.1080/10426507.2015.1085041
Synthesis and characterization of unsymmetric 4-picolyl selenides
Gurjeet Gujrala, Shivani D. Gulatib, Kuldip K. Bhasinc, V. A. Potapovd, and S. V. Amosovad
aDepartment of Chemistry, G.C.G.-11, Chandigarh, 160 011, India; bDepartment of Chemistry, D. A. V. College, Sector-10, Chandigarh, 160 011, India;
cDepartment of Chemistry and Centre of Advanced Studies in Chemistry, Punjab University, Chandigarh, 160 014, India; dA. E. Favorsky Irkutsk Institute
of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk, 664033, Russia
ABSTRACT
ARTICLE HISTORY
Received 18 May 2015
Accepted 17 August 2015
A number of unsymmetrical heteroaryl 4-picolyl selenides have been prepared by lithiation of 4-picoline
using lithium diisopropylamide under cryogenic conditions. The intermediate 4-lithiopicoline formed was
then reacted with elemental selenium followed by the addition of suitable electrophiles to give 4-picolyl
alkyl selenides. 4-Lithiopicoline was also made to react directly with diaryl/dibenzyl diselenide to yield
mixed 4-picolyl aryl/benzyl selenides. All these hitherto unknown selenides were characterized through
various spectroscopic techniques viz., NMR (1H, 13C, 77Se), IR and mass spectrometry.
KEYWORDS
4-Picolyl; phenyl; benzyl;
lithium diisopropylamide
GRAPHICAL ABSTRACT
Introduction
A vast range of bioactive molecules contains the pyridine
unit that may be regarded as a pharmacophoric group and an
essential building block for biological function. Thus, the devel-
opment of new strategies for the preparation of this class of
compounds has become an important endeavor in synthetic
chemistry.20 Due to lack of systematic study on the chemistry
of chalcogen derivatives of 4-picoline, it has not merited special
attention in literature.21–24 Therefore we wish to report a new,
efficient and a convenient method for the synthesis and charac-
terization of mixed selenides of 4-picoline.
Interest in the field of organochalcogenides chemistry has
increased over a period of time, as these compounds have
become increasingly important as reagents and intermediates
in organic synthesis,1–3 transition metal chemistry,4 medicinal
chemistry,5 photography,6 and precursors for metal organic
chemical vapor deposition in semiconductor materials.7 These
compounds are used as a mimic of glutathione peroxidase, an
enzyme known for its antioxidant properties8,9 and also have a
great role as antimicrobial agents10 and are known for their
anticarcinogenic11,12 and hyperglycemic13 properties. Curi-
ously, a literature survey reveals that heteroaryl chalcogenides
have not able to keep pace with the advances made in the field
of aromatic/aliphatic chalcogenides14–16 as their synthetic
methodologies are time consuming, cumbersome, require
expensive reagents and involve drastic conditions.17–19
Results and discussion
Dipyridyl diselenide18a has been prepared by lithiation of 2-
bromopyridine with n-BuLi, subsequent insertion of elemental
chalcogen and followed by the aerial oxidation of lithium
CONTACT Shivani D. Gulati
Chandigarh, India
sdoomra2009@rediffmail.com
DAV College, Research Centre, Sector-10, Chandigarh, Chemistry, #587-J, Sector-21, Panchkula,
© 2016 Taylor & Francis

2
G. GUJRAL ET AL.
2-pyridyl selenolates. However, a similar attempt to lithiate the path that involves the loss of different groups to form various
methyl moiety of 4-picoline using n-BuLi was not successful as species, MC1 peak at m/z 202 [C8H13NSe]C.(62) and other
it led to the lithiation at C-6 position of pyridine ring. n-BuLi peaks are at m/z 172 [C6H6NSe]C. (58), m/z 93 [C6H7N]C
in association with tetramethylethylenediamine, leads to a Chi- (100).
chibabin-type reaction that has been documented in the litera-
Unsymmetrical selenides were also prepared by the cleavage
ture.25 These findings were the driving force to investigate of selenium-selenium bond in diaryl/dibenzyl diselenide with
lithium diisopropylamide, a sterically hindered base for the 4-lithiopicoline. Diaryl/dibenzyl diselenides undergo a reaction
lithiation of 4-picoline to synthesize the orange red colored 4- with 4-lithiopicoline at ¡78ꢀC in dried THF to form aryl/ben-
lithiopicoline. This, on subsequent insertion of selenium at zyl selenolate, which further react with 4-lithiopicoline to
¡78ꢀC with continuous stirring until all elemental selenium afford mixed 4-picolyl aryl/benzyl selenides in excellent yields.
dissolved, led to the formation of a reddish brown solution of It was observed that if the addition of diaryl/dibenzyl diselenide
intermediate selenolate, which was used for further reactions.
occur in one installment, the desired selenide formed was in
Mixed 4-picolyl alkyl selenides were prepared by the reac- very low yield, but slow addition of diaryl/dibenzyl diselenide
tion of intermediate selenolate with suitable alkyl halides, viz., solution in dried THF resulted in high yields of mixed 4-picolyl
methyl iodide and ethyl bromide at ¡78ꢀC in dried THF. After aryl/benzyl selenides (Scheme 2).
the addition of alkyl halides at ¡78ꢀC, the reaction mixture
All these newly synthesized unknown unsymmetrical sele-
was brought to room temperature with continuous stirring. nides are liquids with a foul odor, soluble in organic solvents
The progress of the reaction was monitored by TLC till the such as diethyl ether, chloroform, and dichloromethane. The
completion of reaction. After the usual workup and column compounds were characterized through various spectroscopic
chromatography on silica gel using hexane-ethyl acetate techniques, viz., NMR (1H, 13C, 77Se), IR and mass spectrome-
(9:1, v/v) as eluent, pure 4-picolyl alkyl selenides were obtained try in representative cases. 1H NMR spectra of these mixed sele-
(Scheme 1).
nides in CDCl3 using TMS as an internal reference display
Unsymmetrical 4-picolyl alkyl selenides, prepared by the aromatic protons signals in the range 6.86–8.40 (d ppm)
aforementioned methodology, are yellow viscous foul smelling whereas methylene protons signals appear in 3.47–4.31 (d,
liquids and are stable at room temperature. 4-Picolyl selenides ppm) region. It was observed that methylene protons attached
are less stable as compared to the corresponding alkyl/aryl to the pyridine ring appear downfield compared to the methy-
compounds. However, these compounds are comparable in sta- lene protons attached to phenyl ring in benzyl group due to the
bility with respect to mixed 2-picolyl selenium compounds. deshielding effect of nitrogen in the pyridine ring. Methylene
These compounds are miscible in conventional organic solvents protons appear more downfield when both the rings are pyri-
such as diethyl ether, chloroform, dichloromethane and were dine as in the case of 4-picolyl 2-pyridyl selenide due to the
characterized through various spectroscopic techniques, viz., presence of two electronegative nitrogen atoms in the rings. 13
NMR (1H, 13C, 77Se), IR and mass spectrometry in representa- NMR spectra of these unsymmetrical selenides display aro-
tive cases. matic carbon signals in 120.6–154.2 (d, ppm) range whereas ali-
C
Infrared spectra of these mixed 4-picolyl alkyl selenides were phatic carbon signals for methylene groups appear in the region
recorded in KBr plates in the range 4000–400 cm¡1. Bands in 25.7–30.4 (d, ppm). 77Se NMR spectra of the representative
the region 3100–3000 and 1600–1400 cm¡1 have been assigned mixed 4-picolyl aryl/benzyl selenides with dimethyl selenide as
to C-H and CHC, CHN stretching vibrations of pyridine ring an external reference reveals that the 77Se resonance signals are
whereas those in the range 2900–2800 cm¡1 correspond to very sensitive to even small variation of substituents attached
C-H stretching mode of methyl, methylene groups and 600– to selenium as substituents affect the polarizability of electron
1
400 cm¡1 bands signify C-Se stretching vibrations. H NMR cloud of relatively soft selenium atom. 77Se chemical shift val-
spectra of these selenides obtained in CDCl3 using TMS as an ues in 4-picolyl 2-pyridyl selenide and 4-picolyl benzyl selenide
internal reference, display two sets of signals, one correspond- were obtained at 418.7 (d, ppm) and 338.2 (d, ppm). The down-
ing to aliphatic protons of methyl, methylene groups in the field shift of value in the former case is due to the attachment of
range 1.27–3.61 (d, ppm) and other to the aromatic protons of selenium to the pyridine ring, whereas in the latter case sele-
pyridine ring appearing in the region between 7.06 and 8.44 (d nium is bonded to benzylic carbon of the benzyl group. Mass
ppm). 13C NMR spectra of these compounds in CDCl3 as a ref- spectra of these unsymmetrical selenides contain signals corre-
erence solvent, display aromatic carbon signals in the range sponding to number of characteristic ions, which confirm their
122.2–149.9 (d, ppm) due to magnetically nonequivalent car- structures. As a representative example, the fragmentation pat-
bon atoms of the pyridyl ring whereas aliphatic carbon signals tern of 4-picolyl 2-pyridyl selenide displays the MC1 peak at
for the methyl and methylene groups appear in the region 4.1– m/z 251 [C11H11N2Se]C. (13) and other fragments appear at
26.4 (d, ppm). Fragmentation pattern in the mass spectrum of m/z 170 [C11H10N2]C (100), 169 [C11H9N2]C (42),
representative compound, 4-picolyl ethyl selenide follows the 93 [C6H7N]C (12).
Scheme 1. Preparation of 4-picolyl alkyl selenides.
Scheme 2. Preparation of mixed 4-picolyl aryl/benzyl selenides.

PHOSPHORUS, SULFUR, AND SILICON
3
In an effort to extend the above methodology to prepare reaction mixture was extracted with dichloromethane (3 £
mixed tellurium compounds of 4-picoline, the intermediate tel- 20 mL) and washed with water. The solvent was dried over
lurolate was prepared by insertion of elemental tellurium to 4- anhydrous sodium sulfate and evaporated under reduced pres-
lithiopicoline. Quenching of intermediate tellurolate with sure to afford crude product. It was then subjected to column
methyl iodide did not afford expected telluride, but resulted in chromatography on silica gel using hexane-ethyl acetate
the formation of dimethyl ditelluride as evidenced by 1H NMR. (9:1, v/v) as eluent yielded following unsymmetrical 4-picolyl
A plausible mechanism for the reaction has been demonstrated alkyl selenides.
in Scheme 3.
4-Picolyl methyl selenide, (C5H4NCH2SeCH3), [1]: Yellow
1
Hydrolysis of intermediate selenolate/tellurolate followed by viscous liquid, Yield: 60% ; H NMR (300 MHz, CDCl3/TMS,
its aerial oxidation did not yield the desired 4,4’-dipicolyl dise- 25ꢀC) : d, 1.81 (s, 3H), 3.55 (s, 2H), 7.06–7.08 (d, 2H, J D
lenide, but resulted in the complete decomposition of the reac- 5.7 Hz), 8.39–8.41 (d, 2H, J D 5.7 Hz); 13C NMR (CDCl3/
tion mixture, which led to the formation of the coupled TMS): d, 4.1(-CH3), 26.4(PyCH2), 122.2(C-5), 123.5(C-3),
product, viz., 1,2-bis(4-pyridyl)ethane in quantitative yield.
147.8(C-4), 149.5(C-6), 149.7(C-2); 77Se NMR: d, 179.7; IR
(KBr, cm¡1): 3390, 2922, 2054, 1599, 1557,1415,1276, 1067,
922, 834, 813, 621, 554, 470; MS (EI, %): 188 [C7H10NSe]C
(36); 172 [C6H7NSe]C (12); 107 [C2H3Se]C (9); 93 [C6H7N]C
(100).
Experimental
All synthetic reactions were carried out under a dry and inert
nitrogen atmosphere to prevent oxidation of the oxygen-sensi-
tive selenium/tellurium intermediates. Elemental selenium/tel-
lurium (sigma Aldrich) were activated and stored in a vacuum
desiccator over anhydrous CaCl2. THF was freshly dried and
distilled over sodium-benzophenone prior to use. 4-Picoline
(Fluka) and diisopropylamine (Fluka) were dried and distilled
over KOH pallets. Diphenyl diselenide/ditelluride,26 dibenzyl
diselenide,27 and dipyridyl diselenide18 were prepared by
reported methods. 1H, 13C, and 77Se NMR spectra were
recorded on JEOL AL 300 MHz and BRUKER II 400MHz spec-
trometers in solvents CCl4/CDCl3 using Me4Si (TMS) as an
4-Picolyl ethyl selenide, (C5H4NCH2SeCH2CH3), [2]: Yel-
1
low viscous liquid, Yield: 72%; H NMR (300 MHz, CDCl3/
TMS, 25ꢀC) : d, 1.27–1.33 (t, 3H, J D 7.5 Hz, J D 7.5 Hz), 2.37–
2.51 (q, 2H), 3.61 (s, 2H), 7.10–7.12 (d, 2H, J D 4.8 Hz),8.44
(bs, 2H); 13C NMR (CDCl3/TMS): d, 15.2(Se-CH2), 17.6 (CH3),
25.1(PyCH2), 123.8(C-3,C-5), 148.5(C-4), 149.8(C-6), 149.9(C-
2); 77Se NMR: d, 196.8; IR (KBr, cm¡1): 3399, 2956, 2923, 2056,
1598, 1448, 1413, 1375, 1233, 1066, 991, 831, 812, 734, 620,
553, 470; MS (EI, %): 202 [C8H12NSe]C (62); 172 [C6H6NSe]C
(58); 93 [C6H7N]C (100).
internal standard for H and 13C NMR, whereas 77Se NMR
1
General method for the synthesis of mixed 4-picolyl aryl/
benzyl selenides
spectra were recorded with Me2Se as an external reference. IR
spectra were recorded between KBr plates on a Perkin Elmer
model 1430 ratio recording spectrometer. Mass Spectra (EI,
70 eV) were obtained on VG-705 11–250J and WATERS Q-
TOF MICRO mass spectrometers. Separation and purification
were carried out by column chromatography using silica gel of
100–200 mesh and eluted with mixture of suitable solvents.
To solution of 4-lithiopicoline, obtained from 4-picoline
(0.48 g, 5.2 mmol), diisopropylamine (0.34 g, 6.1 mmol) and n-
o
BuLi (0.18 mL, 6.1 mmol), prepared at ¡78 C under an inert
atmosphere of nitrogen, 5.2 mmoles of dipyridyl/diphenyl/
dibenzyl diselenide, dissolved in dried THF was added drop
wise over a period of 1 h. The reaction mixture was brought to
room temperature slowly with continuous stirring till the com-
pletion of the reaction. Usual workup of the reaction mixture,
followed by column chromatography purification on silica gel
yielded following pure unsymmetrical selenides in nearly quan-
titative yields.
1
Sample H, 13C and 77Se NMR spectra for 3 are shown in the
Supplemental Materials (Figures S1–S3).
General procedure for the preparation of unsymmetrical 4-
picolyl alkyl selenides
To a solution of intermediate selenolate, obtained from 4-pico-
4-Picolyl 2-pyridyl selenide, (C5H4NCH2SeC5H4N), [3]:
1
line (0.48 g, 5.2 mmol), diisopropylamine (0.34 g, 6.1 mmol), Yellow viscous liquid; yield: 80%; H NMR (300 MHz, CDCl3/
n-BuLi (0.18 mL, 6.1 mmol), and elemental selenium (0.48 g, TMS, 25ꢀC): d 4.31 (s, 2H), 6.94–6.98 (m, 1H), 7.16–7.18 (m,
6.05 mmol) at –78ꢀC under an inert atmosphere of nitrogen, 3H), 7.32–7.35 (m, 1H), 8.36–8.40 (t, 3H, J D 6.0 Hz, J D
was added the suitable electrophiles (methyl iodide 0.8 g; 6.0 Hz); 13C NMR (CDCl3/TMS): d, 27.2 (PyCH2Se), 121.7,
5.6 mmol, ethyl bromide, 0.61 g; 5.6 mmol) dissolved in dried 124.0, 125.3, 127.9, 136.6, 148.8, 149.7, 150.1, 154.2; 77Se NMR:
THF (3.0 mL) drop wise to the reaction mixture. After the addi- d, 418.7; IR (KBr, cm¡1): 3409, 2959, 2927, 1722, 1598, 1573,
tion at ¡78ꢀC, the reaction mixture was brought to room tem- 1557, 1449, 1413, 1380, 1278, 1147, 1108, 1042, 986, 810, 755,
perature with continuous stirring. The progress of the reaction 699, 623, 554, 467; MS (EI, %): 251 [C11H11N2Se]C (13); 170
was monitored by TLC. On completion of the reaction, the [C11H10N2]C (100); 169 [C11H9N2]C (42); 93 [C6H7N]C (12).
Scheme 3. Mechanistic Pathway for the formation of dimethyl ditelluride.

4
G. GUJRAL ET AL.
4-Picolyl phenyl selenide, (C5H4NCH2SeC6H5), [4]: Yellow
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1
viscous liquid, yield: 70%; H NMR (300 MHz, CDCl3/TMS,
25ꢀC): d, 3.82 (s, 2H), 6.86–6.88 (d, 2H, J D 4.8 Hz), 7.07–7.14
(m, 3H), 7.26–7.28 (d, 2H, J D 8.0 Hz), 8.29–8.31 (d, 2H, J D
5 Hz); 13C NMR (CDCl3/TMS): d, 30.4 (PyCH2), 123.3, 127.6,
128.8, 134.0, 147.4, 149.4; 77Se NMR: d, 365.5; IR (KBr, cm¡1):
3399, 3067, 1598, 1577, 1558, 1476, 1436, 1413, 1067, 832, 810,
738, 691, 670, 611, 552, 464; MS (EI, %): 250 [C12H12NSe]C
(61); 169 [C12H11N]C (20); 93 [C6H7N]C (100).
12. Terazawa, R.; Garud, D. R.; Hamada, N. H.; Fujita, Y.; Itoh, T.;
Nozawa, Y.; Nakane, K.; Deguchi, T.; Koketsu, M.; Ito, M. Bioorg.
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4-Picolyl benzyl selenide, (C5H4NCH2SeCH2C6H5), [5]:
1
Yellow viscous liquid, yield: 62%; H NMR (300 MHz, CDCl3/
TMS, 25ꢀC): d, 3.47 (s, 2H), 3.61 (s, 2H), 7.01 (s, 2H), 7.13–7.17
(m, 5H), 8.38 (s, 2H); 13C NMR (CDCl3/TMS): d, 25.7 (PhCH2),
27.7 (PyCH2), 123.8, 126.9, 128.5, 128.9, 138.2, 148.1, 149.7; 77Se
NMR: d, 338.2; IR (KBr, cm¡1): 3390, 3026, 2925, 2853, 1721,
1599, 1557, 1493, 1453, 1415, 1279, 1214, 1179, 1067, 1029, 992,
912, 812, 759, 698, 610, 552, 470; MS (EI, %): 264 [C13H14NSe]C
(100); 170 [C7H6Se]C (28); 93 [C6H7N]C (63).
13. Barbosa, N. B.; Rocha, J. B.; Wondracek, D. C.; Perrottoni, J.; Zeni, G.;
Nogueira, C. W. Chem. Biol. Interact. 2006, 163, 230-238.
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Chem. 2013, 2672-2682. (b) Marin, G.; Braga, A. L.; Rosa, A. S.;
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2007, 72, 1241-1245.
In summary, the present studies provide a new, convenient and
an efficient protocol for the synthesis of unknown mixed organyl
selenides via the reaction of intermediate selenolate with suitable 17. (a) Barrios, R. M.; Fregeau, B. M.; Cozens, F. L. J. Org. Chem. 2009, 74,
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759.
electrophiles and by the cleavage of selenium-selenium bond in
diaryl/dibenzyl diselenide with 4-lithiopicoline, as previously
reported synthetic methods suffer due to their lengthy synthetic
procedures, harsh reaction conditions and expensive reagents.
18. (a) Bhasin, K. K.; Jain, V. K.; Kumar, H.; Sharma, S.; Mehta, S. K.;
Singh, J. Synth. Commun. 2003, 33, 977-988. (b) Bhasin, K. K. Phos-
phorous, Sulfur, Silicon Relat. Elem. 2005, 180, 1063-1070. (c)
Hodage, A. S.; Prabhu, C. P.; Phadnis, P. P.; Wadawale, A.; Priyadar-
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C.; Singh, H. B.; Morley, C. P.; Bachman, R.; Cocker, T. M.; Butcher,
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Acknowledgments
Thanks are acknowledged to Prof. Saurav Chatterjee, NIT, Rourkela for
providing 77Se NMR spectral data.
Funding
KKB is thankful to CSIR, Council of Scientific and Industrial Research,
New Delhi for Emeritus Scientist vide scheme 21(967)/13/EMR-II and to
Department of Science and Technology, DST, New Delhi for the research
grant, INT/RUS/RFBR/P-172 (C).
20. Hill, M. D. Chem. Eur. J. 2010, 20, 12052-12062. (b) Henry G. D. Tet-
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