one-pot synthesis of dialkyl 2-(alkyl or aryl)-6-(pyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4 h...
TRANSCRIPT
Month 2013 One-Pot Synthesis of Dialkyl 2-(Al
kyl or aryl)-6-(pyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylate Derivatives via aFour-Component Reaction
Ghasem Marandi,a* Lotfali Saghatforoush,b Soheila Sanati,b and Roya KabiricaShahid Bakeri High Education Center of Miandoab, Urmia University, Urmia, IranbChemistry Department, Payame Noor University, 19395-4697 Tehran, Iran
cFaculty of Chemistry, University of Tabriz, Tabriz, Iran
*E-mail: [email protected]Received October 19, 2011DOI 10.1002/jhet.1615
Published online 00 Month 2013 in Wiley Online Library (wileyonlinelibrary.com).
R
O
Cl + KSCN +CC
CO2R'
CO2R'
+ N N
SH
XX
CH2Cl2
reflux
N
O
SCO2R'
CO2R'S
R
N
N
X
X
R = Me, PhR' = Me, EtX = H, Me
A number of new dialkyl 2-(alkyl or aryl)-6-(pyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylate have been prepared in good yield from the multicomponent reaction between 2-mercapto-pyrimidines and acetylenic diesters with acetyl or benzoyl isothiocyanate.
J. Heterocyclic Chem., 00, 00 (2013).
INTRODUCTION
Multicomponent reactions (MCRs) have been appeared asa powerful tool for the synthesis of many diverse organiccompounds [1,2]. Hence, the novel MCRs designation forsynthesis of valuable compounds with highly applicationsremains the interest of synthetic organic chemist [3–7]. Six-membered heterocycles such as pyrimidines and oxazinesare very important because of their pharmaceutical properties[8–14]. Diverse biological properties of oxazines are antimi-crobial agents, anti-inflammatory agents, acetylcholinesteraseinhibitors, analgesics, and muscle relaxants [15–20]. In con-tinuation of our investigations [21–24] on the developmentof synthesis of novel scaffold for biological purpose, wenow describe the synthesis of 4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylates containing an 2-mercaptopyrimi-dine substitution on C-6 position of the oxazine ring.
RESULTS AND DISCUSSION
We now report a new four-component reaction in whichdialkyl 2-(alkyl or aryl)-6-(pyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylate derivatives 5a–fin 83–93% yields can be synthesized by reacting acetyl orbenzoyl chloride 1, potassium thiocyante 2, and acetylenicdiesters 3 in the presence of 2-mercaptopyrimidine derivatives4 in dry CH2Cl2 as a solvent at reflux condition (Scheme 1).The reactions were carried out by first mixing the acetyl
or benzoyl chloride 1 and potassium thiocyante 2, thenacetylenic diesters 3 and 2-mercaptopyrimidine derivatives4 in dry CH2Cl2, under reflux condition for 6 h.
© 2013 HeteroC
The structures of compounds 5a–f were deduced fromtheir mass, IR, 1H-NMR, 13C-NMR spectra, and elementalanalysis. The mass spectra of these compounds displayedmolecular ion peaks at the appropriate m/z values. The IR,1H-NMR, and 13C-NMR spectroscopic data are in agreementwith the proposed structures. No product other than 5a–fcould be detected by NMR spectroscopy.
The 1H-NMR spectrum of 5a in DMSO-d6 exhibitedsignals for the two methyl groups of the carboxyethyl(d 1.02, 1.25 ppm), methyl group (d 2.33 ppm), carboxyethylmethylenes (d 4.08 and 4.21 ppm), and methine(d 4.53 ppm), H-atoms, along with triplet and doublet atd 7.36 and 8.68 ppm for the pyrimidine moiety.
The 13C-NMR spectrum of 5a exhibited 14 signalsin agreement with the proposed structure. Partial assign-ments of these resonances are given in the ExperimentalSection.
Of special interest are the strong carbonyl absorption bandsat 1711 and 1730 cm�1and fairly strong S═C peak at1197 cm�1 for compound 5a (see the Experimental Section).
Although we have not yet established the mechanism ofthe reaction between 2-mercaptopyrimidine 4 and dialkylacetylenedicarboxylate 3 in the presence of acetyl or benzoylisothiocanate 6 in an experimental manner, a speculativeproposed mechanism for the formation of structures 5 isshown in Scheme 2.
On the basis of the literature survey [6,23–28], it isreasonable to assume that acetyl or benzoyl isothiocyanate6 results from initial addition of the potassium isothiocyante2 to the acetyl or benzoyl chloride 3, and subsequent acetyl
orporation
Scheme 1. Synthesis of 4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylates.
R
O
Cl + KSCN +CC
CO2R'
CO2R'
+ N N
SH
XX1 2
3 4
CH2Cl2
reflux
N
O
SCO2R'
CO2R'S
R
N
N
X
X5
5
a
b
c
d
e
R R'
Me
Et
X
H
% Yield of 5 (M m)a
90 single product ---
Ph Me H
Me 86 57 43
83 57 43Ph Et Me 85 53 47
Et Me 93 single product ---
f Et H 89 71 29
a M and m indicate to major and minor products of 5.
Me
Me
Ph
Me
Scheme 2. Proposed mechanism for synthesis of 4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylates.
5
R
O
Cl + KSCN
1 2
R
O
NCS
3 + 4 S
CO2R'
N
N
X
X
R'O2C
SN
HO
RS
CO2R'
N
N
X
X
R'O2C
SNH
O
R
S
CO2R'
N
N
X
X
R'O2C
SN
O
R
HN
O
S
S
O
OR'
O
OR'
XX
H
S
CO2R'
N
N
X
X
R'O2C
H
6
7
N
O
SCO2R'
CO2R'S
R
N
N
X
X
HN
O
SCO2R'
CO2R'S
R
N
N
X
X
H
(5R,6R)-5 or mirror image(5S,6R)-5 or mirror image
Figure 1. Presentation of two diastereoisomers of 4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylates 5 that have been synthesized via amulticomponent reaction.
G. Marandi, L. Saghatforoush, S. Sanati, and R. Kabiri Vol 000
or benzoyl isothiocyanate 6 is probably attacked by the an-ionic Michael intermediate 7 to generate the heterocyclicsystem 5 (Scheme 2).Although a single product was characterized from the
spectroscopic data such as 1H-NMR and 13C-NMR of thecompounds 5a and 5e, but two diastereoisomer can beobtained because of the two stereogenic center that thisobservation was confirmed by spectroscopic data ofcompounds 5b, 5c, 5d, and 5f (Scheme 1 and Fig. 1).Our attempts for separation of major- and minor-5b, 5c,5d, and 5f were unsuccessful.In conclusion, we have revealed an effective transformation
involving acetyl or benzoyl chloride, potassium isothiocyante,dialkyl acetylenedicarboxylate, and 2-mercaptopyrimidinederivatives affording novel dialkyl 2-(alkyl or aryl)-6-(pyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-xazine-5,6-dicarboxylates. The present procedure has the
Journal of Heterocyclic Chemi
advantage that not only is the reaction performed under neu-tral conditions, but also the reactants can be mixed in a one-pot manner.
stry DOI 10.1002/jhet
Month 2013 One-Pot Synthesis of 4H-1,3-Oxazine Derivatives
EXPERIMENTAL
Melting points and IR spectra were taken on an Electrothermal9100 (USA) apparatus and a Shimadzu Prestige 21 FTIR spectrom-eter (Japan), respectively. The 1H-NMR and 13C-NMR spectra wererecorded on a Bruker DRX-400 AVANCE instrument (Germany)with DMSO-d6 as solvent at 400.1 and 100.6MHz, respectively.Elemental analyses for C, H, andNwere performed using a HeraeusCHN-O-Rapid analyzer (Germany). The mass spectra wererecorded on a Shimadzu GCMS-QP5050A mass spectrometeroperating at an ionization potential of 70 eV. All chemicals werepurchased from Merck, Fluka, and Acros (Germany), and usedwithout further purifications.
General procedure for the preparation of compounds 5a–f. Toamagnetically stirred solution of acetyl or benzoyl chloride (1mmol) andpotassium thiocyante (1mmol) in dry CH2Cl2 (15mL), a mixture ofdialkyl acetylenedicarboxylate (1mmol) in dry CH2Cl2 (2mL) wasadded dropwise at �5�C over 10min, then an appropriate mixture of2-mercaptopyrimidine derivative in dry CH2Cl2 (3mL) was purred tothe reaction pot. The reaction mixture was then allowed to stir for 6hunder reflux condition. After completion of the reaction (TLCmonitoring), solvent was then removed by slow evaporation, and thegenerated precipitate was washed with cold diethyl ether (2� 3mL)and filtered off.
Diethyl 2-methyl-6-(pyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylate (5a). Brown powder; yield:90% (0.34 g), mp=98–101�C. IR (KBr) (nmax, cm
�1): 1730 and1711(C═O), 1197 (C═S). MS (m/z, %): 384 (M++1, 1), 383(M+,2), 355 (13), 324 (28), 216 (100), 110 (36). Anal. Calcd forC15H17N3O5S2 (383.44): C, 46.99; H, 4.47; N, 10.96. Found: C,46.87; H, 4.59; N, 11.13.
1H-NMR (400.1MHz, DMSO-d6): dH 1.02 (3H, t,3JHH=7.1Hz,
CO2CH2CH3), 1.25 (3H, t, 3JHH=6.9Hz, CO2CH2CH3), 2.33(3H, s, N═CCH3), 4.08 (2H, q, 3JHH=6.9Hz, CO2CH2CH3),4.21 (2H, q, 3JHH=7.1Hz, CO2CH2CH3), 4.53 (1H, s, CH), 7.36(1H, t, 3JHH=5.0Hz, CHaryl), 8.68 (2H, d,
3JHH=5.0Hz, 2 CHaryl).13C-NMR (100.6MHz, DMSO-d6): dC 13.48 and 13.57 (2s, 2CO2CH2CH3), 21.92 (s, N═CCH3), 47.93 (s, CH), 61.96 and62.03 (2s, 2 CO2CH2CH3), 116.41 (s, OCS), 119.22 (s, CHaryl),157.39 (s, 2 CHaryl), 163.11 (s, NCNaryl), 166.53 (s, N═CCH3),167.18 and 167.50 (2s, 2 C═O), 170.05 (NC═S).
Dimethyl 2-methyl-6-(4,6-dimethylpyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylate (5b). Dark brownpowder; yield: 86% (0.33 g), mp=110–113�C. IR (KBr)(nmax, cm
�1): 1737 and 1719 (C═O), 1203 (C═S). MS (m/z, %):385 (M++2, 1), 384 (M++1, 1), 383 (M+, 2), 368 (2), 355 (61),340 (47), 223 (100), 191 (36), 140 (27), 107 (41). Anal. Calcd forC15H17N3O5S2 (383.44): C, 46.99; H, 4.47; N, 10.96. Found: C,47.11; H, 4.54; N, 10.89.
Major (57%). 1H-NMR (400.1MHz, CDCl3): dH 2.31 (3H,s, N═CCH3), 2.38 (6H, s, ArMe2), 3.68 and 3.79 (6H, 2s, 2CO2CH3), 5.72 (1H, s, CH), 6.68 (1H, s, CHaryl).
13C-NMR(100.6MHz, CDCl3): dC 22.60 (s, ArMe2), 22.65 (s, N═CCH3),47.40 (s, CH), 51.15 and 51.88 (2s, 2 CO2CH3), 115.13(s, OCS), 116.28 (s, CHaryl), 163.82 (s, 2 Caryl), 166.05(s, NCNaryl), 166.28 (s, N═CCH3), 166.10 and 166.57 (2s, 2C═O), 167.62 (NC═S).
Minor (43%). 1H-NMR (400.1MHz, CDCl3): dH 2.31 (3H,s, N═CCH3), 2.38 (6H, s, ArMe2), 3.76 and 3.81 (6H, 2s, 2CO2CH3), 5.43 (1H, s, CH), 6.76 (1H, s, CHaryl).
13C-NMR(100.6MHz, CDCl3): dC 22.60 (s, ArMe2), 22.65 (s, N═CCH3),
Journal of Heterocyclic Chemi
47.14 (s, CH), 51.63 and 51.80 (2s, 2 CO2CH3), 115.17 (s, OCS),115.89 (s, CHaryl), 164.77 (s, 2 Caryl), 166.05 (s, NCNaryl), 166.28(s, N═CCH3), 166.05 and 166.10 (2s, 2 C═O), 169.69 (NC═S).
Dimethyl 2-phenyl-6-(pyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylate (5c). White powder; yield:83% (0.35g), mp=93–96�C. IR (KBr) (nmax, cm
�1): 1735 (C═O),1203 (C═S). MS (m/z, %): 418 (M++1, 1), 417 (M+, 2), 402 (3),325 (3), 255 (58), 195 (100), 112 (82), 59 (33). Anal. Calcd forC18H15N3O5S2 (417.46): C, 51.79; H, 3.62; N, 10.07. Found: C,51.86; H, 3.54; N, 10.21.
Major (57%). 1H-NMR (400.1MHz, DMSO-d6): dH 3.68and 3.70 (6H, 2s, 2 CO2CH3), 5.63 (1H, s, CH), 7.26–7.28(1H, m, CHphen), 7.38 (1H, t, 3JHH=4.8Hz, CHaryl), 7.51 (1H, t,3JHH=7.8Hz, CHphen), 7.94 (1H, d, 3JHH=7.8Hz, CHphen), 8.65(2H, d, 3JHH=5.0Hz, CHphen), 8.71 (2H, d, 3JHH=4.8Hz,CHaryl).
13C-NMR (100.6MHz, DMSO-d6): dC 47.49 (s, CH),53.07 and 53.11 (2s, 2 CO2CH3), 118.15 (s, OCS), 119.18 (s,CHaryl), 122.15, 127.18, 129.00 and 136.07 (4s, 5 CHphen andCphen), 158.05 (s, 2 CHaryl), 158.16 (s, N═CC6H5), 158.60(s, NCNaryl), 164.17 and 165.12 (2s, 2 C═O), 169.69 (NC═S).
Minor (43%). 1H-NMR (400.1MHz, DMSO-d6): dH 3.63and 3.75 (6H, 2s, 2 CO2CH3), 5.38 (1H, s, CH), 7.29–7.31(1H, m, CHphen), 7.38 (1H, t, 3JHH = 4.8 Hz, CHaryl), 7.51(1H, t, 3JHH = 7.8Hz, CHphen), 7.96 (1H, d, 3JHH = 7.6Hz,CHphen), 8.61 (2H, d, 3JHH = 5.0 Hz, CHphen), 8.71 (2H,d, 3JHH = 4.8Hz, CHaryl).
13C-NMR (100.6MHz, DMSO-d6):dC 47.38 (s, CH), 52.18 and 52.31 (2s, 2 CO2CH3), 118.10(s, OCS), 119.02 (s, CHaryl), 122.18, 126.15, 129.21 and135.85 (4s, 5 CHphen and Cphen), 157.36 (s, 2 CHaryl), 159.02(s, N═CC6H5), 158.41 (s, NCNaryl), 163.97 and 165.12 (2s, 2C═O), 170.03 (NC═S).
Diethyl 2-phenyl-6-(4,6-dimethylpyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylate (5d). Lightyellow powder; yield: 85% (0.40 g), mp=100–103�C. IR (KBr)(nmax, cm
�1): 1739, 1727 (C═O), 1195 (C═S). MS (m/z, %): 474(M++1, 1), 473 (M+, 2), 444 (16), 428 (46), 383 (54), 318 (100),305 (68). Anal. Calcd for C22H23N3O5S2 (473.56): C, 55.80; H,4.90; N, 8.87. Found: C, 55.91; H, 4.84; N, 8.79.
Major (53%). 1H-NMR (400.1MHz, DMSO-d6): dH 1.14(3H, t, 3JHH=7.0Hz, CO2CH2CH3), 1.18 (3H, t, 3JHH=7.1Hz,CO2CH2CH3), 2.38 (6H, s, ArMe2), 4.11–4.13 (2H, m,CO2CH2CH3), 4.14–4.19 (2H, m, CO2CH2CH3), 4.55 (1H, s,CH), 6.90 (1H,s, CHaryl), 7.44–7.48 (1H, m, CHphen), 7.65 (2H, t,3JHH=7.8Hz, 2 CHphen), 8.15 (2H, d, 3JHH=8.4Hz, 2 CHphen).13C-NMR (100.6MHz, DMSO-d6): dC 13.55 and 13.78 (2s, 2CO2CH2CH3), 23.17 (s, ArMe2), 48.09 (s, CH), 61.53 and 61.68(2s, 2 CO2CH2CH3), 116.53 (s, CHaryl), 117.50 (s, OCS), 123.14,127.75, 128.35 and 131.10 (4s, 5 CHphen and Cphen), 164.50 (s,C═O), 165.00 (s, 2 Caryl), 166.23 (s, C═O), 166.58 (s,N═CC6H5), 167.22 (s, NCNaryl), 167.67 (NC═S).
Minor (47%). 1H-NMR (400.1MHz, DMSO-d6): dH 1.05(3H, t, 3JHH=6.8Hz, CO2CH2CH3), 1.16 (3H, t, 3JHH=7.0Hz,CO2CH2CH3), 2.33 (6H, s, ArMe2), 4.05–4.09 (2H, m,CO2CH2CH3), 4.21–4.30 (2H, m, CO2CH2CH3), 5.27 (1H, s,CH), 7.00 (1H,s, CHaryl), 7.64 (1H, t, 3JHH=7.2Hz, CHphen),7.80–7.88 (2H, m, 2 CHphen), 7.94 (2H, d, 3JHH=7.0Hz, 2CHphen).
13C-NMR (100.6MHz, DMSO-d6): dC 13.61 and 13.98(2s, 2 CO2CH2CH3), 23.36 (s, ArMe2), 48.13 (s, CH), 61.02 and61.95 (2s, 2 CO2CH2CH3), 116.53 (s, CHaryl), 117.35 (s, OCS),122.44, 125.89, 128.11 and 129.63 (4s, 5 CHphen and Cphen),164.11 (s, 2 Caryl), 165.21 (s, C═O), 166.83 (s, N═CC6H5), 167.17(s, NCNaryl), 167.35 (s, C═O), 167.54 (NC═S).
stry DOI 10.1002/jhet
G. Marandi, L. Saghatforoush, S. Sanati, and R. Kabiri Vol 000
Diethyl 2-methyl-6-(4,6-dimethylpyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylate (5e). Dark brownpowder; yield: 93% (0.38g), mp=123–126�C. IR (KBr)(nmax, cm
�1): 1739 and 1726 (C═O), 1195 (C═S). MS (m/z, %):412 (M++1, 1), 411 (M+, 2), 383 (15), 367 (28), 352 (27), 212(100), 140 (34). Anal. Calcd for C17H21N3O5S2 (411.50): C, 49.62;H, 5.14; N, 10.21. Found: C, 49.69; H, 5.05; N, 10.29.
1H-NMR (400.1MHz, DMSO-d6): dH 1.14 (3H, t, 3JHH=6.5Hz,CO2CH2CH3), 1.17 (3H, t, 3JHH=7.0Hz, CO2CH2CH3), 2.26 (3H,s, N═CCH3), 2.44 (6H, s, ArMe2), 4.13 (2H, q, 3JHH=7.0Hz,CO2CH2CH3), 4.16 (2H, q, 3JHH=6.5Hz, CO2CH2CH3), 5.55(1H, s, CH), 7.00 (1H,s, CHaryl).
13C-NMR (100.6MHz, DMSO-d6): dC 13.75 and 13.88 (2s, 2 CO2CH2CH3), 22.76 (s, N═CCH3),23.41 (s, ArMe2), 48.15 (s, CH), 61.55 and 61.74 (2s, 2CO2CH2CH3), 116.60 (s, OCS), 117.73 (s, CHaryl), 161.47 (s, 2Caryl), 167.14 (s, N═CCH3), 167.27 (s, C═O), 167.87 (s, NCNaryl),167.93 (s, C═O), 169.19 (NC═S).
Diethyl 2-phenyl-6-(pyrimidin-2-ylthio)-4-thioxo-5,6-dihydro-4H-1,3-oxazine-5,6-dicarboxylate (5f). Yellow powder; yield:89% (0.40 g), mp=107–110�C. IR (KBr) (nmax, cm
�1): 1739 and1724 (C═O), 1206 (C═S). MS (m/z, %): 446 (M++1, 1), 445(M+, 1), 401 (2), 395 (8), 282 (66), 209 (100), 181 (51). Anal.Calcd for C20H19N3O5S2 (445.51): C, 53.92; H, 4.30; N, 9.43.Found: C, 54.07; H, 4.36; N, 9.32.
Major (71%). 1H-NMR (400.1MHz, DMSO-d6): dH 1.14(3H, t, 3JHH = 7.5Hz, CO2CH2CH3), 1.18 (3H, t, 3JHH = 7.3Hz,CO2CH2CH3), 4.14–4.18 (4H, m, 2 CO2CH2CH3), 5.56 (1H, s,CH), 7.27 (1H, t, 3JHH = 4.8Hz, CHaryl), 7.37 (1H, m, CHphen),7.45 (1H, t, 3JHH = 7.3Hz, CHphen), 7.50 (1H, t, 3JHH = 7.6Hz,CHphen), 7.88 (1H, d, 3JHH = 7.3Hz, CHphen), 7.95 (1H, d,3JHH = 7.2Hz, CHphen), 8.65 (2H, d, 3JHH = 4.8Hz, 2 CHphen).13C-NMR (100.6MHz, DMSO-d6): dC 13.62 and 13.77 (2s, 2CO2CH2CH3), 47.52 (s, CH), 61.68 and 61.80 (2s, 2CO2CH2CH3), 118.07 (s, OCS), 119.13 (s, CHaryl), 123.07,127.38, 129.15 and 131.18 (4s, 5 CHphen and Cphen), 158.06(s, N═CC6H5), 158.55 (s, 2 CHaryl), 167.47 (s, C═O), 168.47(s, NCNaryl), 169.13 (s, C═O), 169.33 (NC═S).
Minor (29%). 1H-NMR (400.1MHz, DMSO-d6): dH 1.103H, t, 3JHH=7.1Hz, CO2CH2CH3), 1.15 (3H, t, 3JHH=7.0Hz,CO2CH2CH3), 4.06 (2H, q, 3JHH=7.1Hz, CO2CH2CH3), 4.23(2H, q, 3JHH = 7.0Hz, CO2CH2CH3), 5.33 (1H, s, CH), 7.30(1H, t, 3JHH = 4.6Hz, CHaryl), 7.30–7.37 (1H, m, CHphen),7.48 (1H, t, 3JHH=7.5Hz, CHphen), 7.64 (1H, m, CHphen), 7.66(1H, m, CHphen), 8.15 (1H, d, 3JHH=7.3Hz, CHphen), 8.61(2H, d, 3JHH=4.6Hz, 2 CHphen).
13C-NMR (100.6MHz,DMSO-d6): dC 13.48 and 13.53 (2s, 2 CO2CH2CH3), 47.65(s, CH), 61.47 and 61.59 (2s, 2 CO2CH2CH3), 118.48(s, OCS), 119.58 (s, CHaryl), 123.11, 127.54, 129.18 and130.72 (4s, 5 CHphen and Cphen), 157.95 (s, N═CC6H5),158.57 (s, 2 CHaryl), 167.71 (s, C═O), 168.43 (s, NCNaryl),169.08 (s, C═O), 169.56 (NC═S).
Journal of Heterocyclic Chemi
Acknowledgment. We gratefully acknowledge the financial supportof the Research Council of the Payame Noor University of Khoy.
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stry DOI 10.1002/jhet