Efficient preparation of 2, 2′-disubstituted-3, 3′-(1, 4-phenylene)bis-thienopyrimidin-4-ones based on an aza-Wittig reaction

Article abstract of DOI:10.1002/jhet.1579

Tandem aza-Wittig reaction of iminophosphorane with 1, 4-phenylene diisocyanate followed by intramolecular heteroconjugate addition annulation after addition of a nucleophilic reagent (amine, phenol, and alcohol), in the presence of catalytic K₂

Full text of DOI:10.1002/jhet.1579

850
Efficient Preparation of 2,20-Disubstituted-3,30-(1, 4-phenylene)bis-
Vol 50
thienopyrimidin-4-ones Based on an aza-Wittig Reaction
*
Kai Yan, Hong Chen, Qiuhong Dai, and Mingguo Liu
Hubei Key Laboratory of Natural Products Research and Development, China Three Gorges University, Yichang, 443002,
People’s Republic of China
*
E-mail: mgliu0427@yahoo.com.cn
Received August 25, 2011
DOI 10.1002/jhet.1579
Published online 27 June 2013 in Wiley Online Library (wileyonlinelibrary.com).
Tandem aza-Wittig reaction of iminophosphorane with 1,4-phenylene diisocyanate followed by intramolecular
heteroconjugate addition annulation after addition of a nucleophilic reagent (amine, phenol, and alcohol), in the
presence of catalytic K2CO3 or NaOR, gives selectively the functionalized substituted 2,20-di(alkylamino, aryloxy)-
3,30-(1, 4-phenylene)bis(thieno[3,2-d]pyrimidin-4(3H)-ones) and 2,20-di(alkylamino or alkoxy)-3,30-(1, 4-pheny-
lene)bis(3,5,6,7-tetrahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-ones).
J. Heterocyclic Chem., 50, 850 (2013).
INTRODUCTION
2-d]pyrimidin-4(3H)-ones) and 2, 20-di(alkylamino, alkoxy)-
3, 30-(1, 4-phenylene)bis(3, 5, 6, 7-tetrahydro-4H-cyclopenta
[4, 5]thieno[2, 3-d]pyrimidin-4-ones).
The development of efficient and mild synthetic methods
for heterocyclic compounds represents a broad area of or-
ganic chemistry. In recent years, the aza-Wittig reactions
of iminophosphoranes have received increased attention
in view of their utility in the synthesis of heterocyclic
compounds, especially nitrogen-containing heterocyclic
compounds [1]. The intermolecular aza-Wittig reaction
followed by cyclizing has been utilized for the synthesis
of many important nitrogen heterocycles [2]. Especially
thienopyrimidine derivatives, they are an important class
of S-heterocyclic and N-heterocyclic compounds in phar-
maceutical discovery research because of their significant
activities such as anticancer, antifungal, and antibacterial
activities [3–6].
Iminophosphoranes-containing thiophene ring, derived
from aminothiophene, have proved to be very versatile
building blocks for the construction of fused thienopyrimi-
dine system by the aza-Wittig reaction. We have previ-
ously published the synthesis of fused thienopyrimidines
on the basis of the tandem aza-Wittig reaction. As a contin-
uation of our work on the aza-Wittig-type methodology,
we report here a simple, general, and effective strategy
for the preparation of substituted derivatives of 2, 20-di
(alkylamino, aryloxy)-3, 30-(1, 4-phenylene)bis(thieno[3,
RESULTS AND DISCUSSION
In recent years, our work has been concerned with the dis-
covery and development of synthesis of new heterocyclic
compounds containing thienopyrimidine moiety. We have
previously reported on the synthesis of novel tricyclic ring
systems, containing the thienopyrimidine skeleton, with
antibacterial and antifungal activities [7]. Among them, 3,
30-diphenyl-2, 20-(1, 3-phenylenedioxy)bis(3, 5, 6, 7-tetrahy-
dro-4H-cyclopenta[4, 5]thieno[2, 3-d]pyrimidin-4-ones),
because of two connected thienopyrimidine, showed signifi-
cant activity of anticitrinin [8]. We now describe here, as a
further extension of the aza-Wittig-type methodology, the
synthesis of connected thienopyrimidines.
Heterocyclic compounds 5a–g and 6a-g were obtained
in a reaction of the corresponding iminophosphoranes with
aromatic isocyanates, followed by heterocyclization on ad-
dition of amines, phenol, or alcohol.
The key iminophosphoranes 2a–b were obtained by a
modified Kirsanov reaction of the aminothiophene 1a–b
with in situ prepared dichlorotriphenylphosphorane using
© 2013 HeteroCorporation

July 2013
Efficient Preparation of 2, 20-Disubstituted-3, 30-(1, 4-phenylene)bis-thienopyrimidin-4-ones
851
Based on an aza-Wittig Reaction
a hexachloroethane-triphenylphosphine-triethylamine reagent
system (Scheme 1). The molecular structure of iminophpo-
sphoranes was supported by the spectral data and elemental
analysis.
Moreover, we considered the possibility of extending
this design strategy to the preparation of 2, 20-di(alkylamino
or alkoxy)-3, 30-(1, 4-phenylene)bis(3, 5, 6, 7-tetrahydro-
4H-cyclopenta[4, 5]thieno[2, 3-d]pyrimidin-4-ones) 6. We
reacted 1, 4-phenylene diisocyanate with iminophosphor-
ane 2b, under similar reaction conditions, which furnished
new compounds 6 (Scheme 3).
Iminophosphorane 2 reacted with half equiv of 1,4-
Phenylene Diisocyanate (PPDI) to give carbodiimide 3,
which was allowed to react with amine to provide guani-
dine intermediates 4. In the presence of a catalytic amount
of sodium ethoxide, 4 were converted easily to substituted
5a–e at room temperature. While the formation of pro-
ducts 5f–g were carried out by heterocyclization on addi-
tion of phenols in the presence of K2CO3 (Scheme 2)
Owing to the unstability of carbodiimide 3, the prepara-
tion of carbodiimides 3 must be carried out at low temper-
ature (0–5ꢀC) and long reaction time (8–l2 h) under dry
conditions. Otherwise, hydrolysis or polymerization side
reaction of carbodiimide should take place, which will re-
sult in low yields [9].
EXPERIMENTAL
Measurements. Melting points were uncorrected. Mass spectra
were measured on a Finnigan Trace MS spectrometer (California,
USA). 1H and 13C NMR spectra were recorded in CDCl3 on Varian
(California, USA) Mercury 600 and 400 spectrometers, and
resonances were given in d relative to TMS. Elementary analyses
were carried out on a Vario EL III elementary analysis instrument.
Preparation of iminophosphorane 2.
To a mixture of
aminothiophene 1 (8 mmol), PPh3 (3.14 g, 12 mmol), and C2Cl6
(2.84 g, 12 mmol) in dry MeCN (40 mL) was added dropwise
NEt3 (2.42 g, 24 mmol) at room temperature. After stirring for
4 h, the solvent was removed under reduced pressure, and
the residue was recrystallized from EtOH to give methyl
3-[(triphenylphosphoranylidene)amino]thiophene-2-carboxylate 2a
or ethyl 2-[(triphenylphosphoranylidene)amino]-5, 6-dihydro-4H-
cyclopenta[b]thiophene-3-carboxylate 2b.
The participation of carbodiimide 3 and the corresponding
guanidine-type compound 4 as intermediates in this process
has been confirmed experimentally [10].
2a: White crystals (yield 71%). mp: 115–117ꢀC; 1H NMR
(CDCl3, 400 MHz) d (ppm): 7.82–7.45 (m, 15H, Ar-H), 7.03
(d, J = 5.2 Hz, 1H, Ar-H), 6.20 (d, J = 5.2 Hz, 1H, Ar-H), 3.84
(s, 3H, OCH3); 13C NMR (CDCl3, 100 MHz) d (ppm): 163.8,
156.0, 132.5, 131.8, 130.9, 129.9, 129.3, 129.1, 128.7, 128.5,
128.3, 124.7, 50.8; MS m/z (%): 417 (M+, 86), 384 (43), 358
(100), 183 (66), 77 (87), 59 (59); Anal. Calcd for C24H20NO2PS:
C, 69.05; H, 4.83; N, 3.36. Found C, 69.29; H, 4.61; N, 3.59.
2b: Yellow solid (yield 86%). mp: 183–184ꢀC. 1H NMR
(CDCl3, 400 MHz) d (ppm): 7.47–7.88 (m, 15H, Ar-H), 4.27
(q, J = 6.8 Hz, 2H, OCH2), 2.88 (t, J = 6.4 Hz, 2H, CH2), 2.59
Scheme 1. Preparation of iminophosphorane.
Scheme 2. Preparation of compounds 5a–g.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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K. Yan, H. Chen, Q. Dai, and M. Liu
Vol 50
Scheme 3. Preparation of compounds 6a–g.
(t, J = 6.4 Hz, 2H, CH2), 2.19 (m, 2H, CH2), 1.34 (t, J = 6.8 Hz,
3H, CH3); MS m/z: 471 (M+, 79); Anal. Calcd for C28H26NO2PS:
C, 71.32; H, 5.56; N, 2.97. Found: C, 71.55; H, 5.32; N, 3.21.
General procedure of 2, 20-dialkylamino-3, 30-(1, 4-phenylene)
bis(thieno[3, 2-d]pyrimidin ꢁ4(3H)-ones) 5a–e. To a solution
of iminophosphorane 2a (0.84 g, 2 mmol) in dry CH2Cl2 (5 mL)
was added 1, 4-phenylene diisocyanate (1mmol) at room
temperature. Then, the reaction mixture was left to stand for 8–
12h at 0–5ꢀC until the iminophosphorane had disappeared (TLC
monitored). To the solution prepared earlier was added amine
(2mmol). After the reaction mixture was allowed to stand for
0.5–6 h (TLC monitored), the solvent was removed, and
anhydrous ethanol (10mL) with several drops of EtONa in EtOH
was added. The solution was then concentrated under reduced
pressure, and residual was recrystallized from CH2Cl2 and EtOH
(1:2) to give compounds 5a–f.
5d: 2, 20-Di(diisobutylamino)-3, 30-(1, 4-phenylene)bis(thieno
[3, 2-d]pyrimidin-4 (3H)-one). White crystals (yield 47%). mp
>300ꢀC. 1H NMR (CDCl3, 400 MHz) d (ppm): 7.73–7.15
(m, 8H, Ar-H), 2.91 (d, J = 7.2 Hz, 8H, 4NCH2), 1.86 (m, 4H,
4CH), 0.81 (m, 24H, 8CH3); 13C NMR (CDCl3, 150 MHz) d
(ppm): 159.0, 157.0, 156.4, 137.3, 134.5, 129.1, 124.4, 116.0,
58.5, 27.1, 20.5; MS m/z (%): 632 (M+, 14), 589 (100), 533
(71), 477 (56), 366 (35), 207 (34), 151 (90); Anal. Calcd for
C34H44N6O2S2: C, 64.52; H, 7.01; N, 13.28. Found: C, 64.79;
H, 6.77; N, 13.59.
5e: 2, 20-Di(dihexylamino)-3, 30-(1, 4- phenylene)bis(thieno
[3, 2-d]pyrimidin-4 (3H)-one).
White crystals (yield 39%).
mp: 100–101ꢀC. 1H NMR (CDCl3, 600 MHz) d (ppm): 7.73–
7.18 (m, 8H, Ar-H), 3.03 (t, J = 7.8 Hz, 8H, 4NCH2), 1.35–1.15
(m, 32H, 16CH2), 0.85 (t, J = 6.6 Hz, 12H, 4CH3); 13C NMR
(CDCl3, 150 MHz) d (ppm): 159.0, 156.8, 156.6, 137.2, 134.5,
129.1, 124.5, 116.7, 51.0, 31.4, 27.2, 26.7, 22.5, 14.0; MS m/z
(%): 744 (M+, 26), 674 (41), 493 (100), 436 (88), 250 (36), 151
(34); Anal. Calcd for C42H60N6O2S2: C, 67.70; H, 8.12; N,
11.28. Found: C, 67.95; H, 7.92; N, 11.53.
5a: 2, 20-Di(dipropylamino)-3, 30-(1, 4-phenylene)bis(thieno
[3, 2-d]pyrimidin-4 (3H)-one).
White crystals (yield 51%).
mp: 248ꢀC. 1H NMR (CDCl3, 400 MHz) d (ppm): 7.74–7.18
(m, 8H, Ar-H), 3.01 (t, J = 7.8 Hz, 8H, NCH2), 1.35 (m, 8H, CH2),
0.78 (t, J = 7.4 Hz, 12H, CH3); 13C NMR (CDCl3, 150 MHz)
d (ppm): 159.2, 156.9, 156.8, 137.4, 134.5, 129.5, 124.6, 116.9,
53.0, 20.7, 11.6; Anal. Calcd for C30H36N6O2S2: C, 62.47; H,
6.29; N, 14.57. Found: C, 62.69; H, 6.01; N, 14.79.
General procedure of 2, 20-diaryloxy-3, 30-(1, 4-phenylene)bis
(thieno[3, 2-d]pyrimidin ꢁ4(3H)-ones) 5f–g. To a solution of
iminophosphorane 2a (0.84 g, 2 mmol) in dry CH2Cl2 (5 mL) was
added 1, 4-phenylene diisocyanate (1 mmol) at room temperature.
Then, the reaction mixture was left to stand for 8–12 h at 0–5ꢀC
until the iminophosphorane had disappeared (TLC monitored).
The solvent was evaporated, and the residue was dissolved in
MeCN (3 mL), a catalytic amount of K2CO3 was added, and the
mixture was refluxed for 5 h (TLC monitored) then filtered off.
The filtrate was then concentrated under reduced pressure, and
residue was recrystallized from CH2Cl2 and EtOH (1:2) to give
compounds 5f–g.
5b: 2, 20-Di(diisopropylamino)-3, 30-(1, 4-phenylene)bis(thieno
[3, 2-d]pyrimidin-4 (3H)-one). White crystals (yield 52%). mp:
>300ꢀC. 1H NMR (CDCl3, 600 MHz) d (ppm): 7.72–7.16
(m, 8H, Ar-H), 3.55 (m, 4H, 4NCH), 1.13 (d, 24H, 8CH3); 13C
NMR (CDCl3, 150 MHz) d (ppm): 159.8, 156.7, 155.4, 138.0,
134.2, 129.8, 124.8, 117.2, 50.2, 21.6; MS m/z (%): 576 (M+, 2),
367 (17), 277(17), 210 (43), 151 (100), 100 (48); Anal. Calcd for
C30H36 N6O2S2: C, 62.47; H, 6.29; N, 14.57. Found: C, 62.71; H,
6.02; N, 14.79.
5f: 2, 20-Di[4-(methylthio)phenoxy]-3, 30-(1, 4-phenylene)bis
5c: 2, 20-Di(dibutylamino)-3, 30-(1, 4-phenylene)bis(thieno[3,
(thieno[3, 2-d] pyrimidin-4(3H) -one).
White crystals (yield
45%). mp: 190–192ꢀC. 1H NMR (CDCl3, 600 MHz) d (ppm):
7.77–7.09 (m, 16H, Ar-H), 2.49 (s, 6H, 2SCH3); MS m/z (%):
654 (M+, 14), 268 (17), 247 (31), 200 (27), 139 (100), 111
(29), 96 (74); Anal. Calcd for C32H22N4O4S4: C, 58.70; H,
3.39; N, 8.56. Found: C, 58.95; H, 3.11; N, 8.79.
2-d]pyrimidin-4(3H) -one).
White crystals (yield 49%). mp:
174–176ꢀC. 1H NMR (CDCl3, 400 MHz) d (ppm): 7.74–7.18
(m, 8H, Ar-H), 3.04 (t, J = 7.4 Hz, 8H, 4NCH2), 1.33–1.16
(m, 16H, 8CH2), 0.86(t, J = 7.2 Hz, 12H, 4CH3); 13C NMR
(CDCl3, 150 MHz) d (ppm): 159.0, 156.7, 156.6, 137.1, 134.4,
129.2, 124.5, 116.7, 50.8, 29.3, 20.2, 13.7; MS m/z (%): 632
(M+, 4), 380 (20), 151 (42), 125 (29), 57 (65), 41 (100); Anal.
Calcd for C34H44N6 O2S2: C, 64.52; H, 7.01; N, 13.28. Found:
C, 64.79; H, 6.78; N, 13.54.
5g: 2, 20-Di[3-(trifluoromethyl)phenoxy]-3, 30-(1, 4-phenylene)
bis(thieno[3, 2-d] pyrimidin-4(3H)-one). White crystals (yield
1
55%). mp >300ꢀC. H NMR (CDCl3, 600 MHz) d (ppm): 7.80–
7.13 (m, 16H, Ar-H); MS m/z (%): 698 (M+, 54), 537 (64), 269
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Efficient Preparation of 2, 20-Disubstituted-3, 30-(1, 4-phenylene)bis-thienopyrimidin-4-ones
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Based on an aza-Wittig Reaction
(100), 188 (32), 96 (74); Anal. Calcd for C32H16F6N4O4 S2: C,
55.01; H, 2.31; N, 8.02. Found: C, 55.27; H, 2.01; N, 8.27.
General procedure of 2, 20-di(alkylamino)-3, 30-(1, 4-
phenylene)bis(3, 5, 6, 7-tetrahydro -4H-cyclopenta[4, 5]thieno[2,
6f: 2, 20-Di(n-butylamino)-3, 30-(1, 4-phenylene)bis(3, 5, 6, 7-
tetrahydro-4H-cyclopenta[4, 5]thieno[2, 3-d]pyrimidin-4-
1
one). White crystals (yield 64%). mp: 270–272ꢀC. H NMR
(CDCl3, 600 MHz) d (ppm): 7.49(s, 4H, Ar-H), 5.18 (s, 2H,
2NH), 3.37–1.27 (m, 24H, 12CH2), 0.91–0.89 (t, 6H, 2CH3);
13C NMR (CDCl3, 150 MHz) d (ppm): 171.9, 159.2, 150.1,
139.5, 136.2, 131.9, 131.6, 111.4, 41.9, 31.3, 29.4, 29.0, 27.7,
20.0, 13.8; MS m/z: 600 (M+, 100); Anal. Calcd for C40H52N6
O2S2: C, 67.38; H,7.35;N,11.79. Found: C, 67.59; H, 7.07; N,
3-d]pyrimidin-4-ones) 6a–f.
The experimental process is
similar to the formation of 2, 20-dialkylamino-3, 30-(1, 4-phenylene)
bis(thieno[3, 2-d]pyrimidin-4(3H)-ones) 5a–e.
6a: 2, 20-Di(dipropylamino)-3, 30-(1, 4-phenylene)bis(3, 5, 6,
7-tetrahydro-4H-cyclopenta[4,
5]thieno[2,
3-d2]pyrimidin-4-
1
ones). White crystals (yield 41%). mp: 253–255.6ꢀC. H NMR
(CDCl3, 600 MHz) d (ppm): 7.40–7.27 (d, 4H, Ar-H), 2.99–1.35
(m, 28H, 14CH2), 0.76 (t, J=6.6Hz, 4CH3); 13C NMR (CDCl3,
150 MHz) d (ppm): 168.7, 159.3, 154.3, 140.1, 137.2, 134.3, 129.2,
114.3, 53.4, 52.3, 29.4, 28.9, 27.7, 20.6, 11.5; MS m/z (%): 656
(M+, 100). Anal. Calcd for C31H34N6O2S2: C, 63.45; H, 5.84; N,
14.32; Found: C, 63.69; H, 5.61; N, 14.58.
12.01.
Synthesis of 2, 20-dipropoxy-3, 30-(1, 4-phenylene)bis(3, 5, 6,
7-tetrahydro-4H-cyclopenta[4, 5] thieno[2, 3-d]pyrimidin-4-
one) 6g. To the solution of carbodiimides prepared earlier in
C3H7OH (15 mL) was added 1 equiv of C3H7ONa in C3H7OH.
The mixture was stirred for 6 h at room temperature (TLC
monitored). The solution was condensed, and the residue was
recrystallized from CH2Cl2 and EtOH to give 6g. White crystals
6b: 2, 20-Di(diisopropylamino)-3, 30-(1, 4-phenylene)bis(3, 5,
6, 7-tetrahydro-4H-cyclopenta[4, 5] thieno[2, 3-d]pyrimidin-4-
1
(yield 61%). mp: 276.6–277.6ꢀC. H NMR (CDCl3, 600 MHz)
White crystals (yield 69%). mp: 173ꢀC. 1H NMR
d (ppm): 7.30 (s, 4H, Ar-H), 4.31 (s, 4H, OCH2), 3.02 (s, 4H,
CH2), 2.93 (s, 4H, CH2), 2.44 (m, 4H, CH2), 1.65 (s, 4H, CH2),
0.84 (s, 6H, CH3); MS m/z: 574 (M+, 20); Anal. Calcd for
C30H30 N4O4S2: C, 62.70; H, 5.26; N, 9.75. Found: C, 62.91;
H, 5.05; N, 10.02.
ones).
(CDCl3, 600 MHz) d (ppm): 7.36–7.26 (d, 4H, ArH), 3.53–2.89
(m, 12H, 6CH2), 2.44–2.39 (m, 4H, 4CH), 0.12–0.11 (d, 24H,
8CH3); 13C NMR (CDCl3, 150 MHz) d (ppm): 168.3, 159.9,
153.2, 140.0, 137.8, 134.5, 129.6, 114.7, 50.2, 29.4, 28.9, 27.7,
21.6. MS m/z (%): 656 (M+, 100). Anal. Calcd for
C31H34N6O2S2: C, 63.45; H, 5.84; N, 14.32; Found: C, 63.68;
H, 5.59; N, 14.57.
Acknowledgments. We gratefully acknowledge the Science Foun-
dation of Hubei Province Education Department, China (project no.
D20091301) and the Excellent Fund for Scientific Research and
Special Projects in China Three Gorges University, China
(project no. KJ 2009 B004) for the financial support of this work.
6c: 2, 20-Di(dibutylamino)-3, 30-(1, 4-phenylene)bis(3, 5, 6, 7-
tetrahydro-4H-cyclopenta[4, 5] thieno[2, 3-d]pyrimidin-4-
ones).
White crystals (yield 48%). mp: 253.8–254.5ꢀC. 1H
NMR (CDCl3, 600 MHz) d (ppm): 7.40–7.28 (d, 4H, ArH),
3.03–1.16 (m, 36H, 18CH2), 0.85 (t, J = 7.2 Hz, 12H, 4CH3);
13C NMR (CDCl3, 150 MHz) d (ppm): 168.7, 159.2, 154.3,
140.1, 137.1, 134.3, 129.1, 114.3, 50.9, 29.5, 29.4, 28.9, 27.7,
20.2, 13.7. MS m/z (%): 712 (M+, 100). Anal. Calcd for
C33H38N6O2S2: C, 64.47; H, 6.23; N, 13.67; Found: C, 64.71;
H, 6.01; N, 13.95.
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6d: 2, 20-Di(diisobutylamino)-3, 30-(1, 4-phenylene)bis(3, 5, 6,
7-tetrahydro-4H-cyclopenta[4, 5] thieno[2, 3-d]pyrimidin-4-
1
ones). White crystals (yield 63%). mp: 269–271ꢀC. HNMR
(CDCl3, 600 MHz) d (ppm): 7.43–7.26 (d, 4H, Ar-H), 2.99–
2.39 (m, 24H, 12CH2), 1.84 (s, 4H, 4CH), 0.81–0.79 (d, 24H,
8CH3); 13C NMR (CDCl3, 150 MHz) d (ppm): 168.9, 159.1,
154.2, 140.1, 137.3, 133.9, 129.1, 113.8, 58.6, 29.4, 28.9, 27.7,
27.2, 20.5. MS m/z (%): 712 (M+, 100). Anal. Calcd for
C33H38N6O2S2: C, 64.47; H, 6.23; N, 13.67; Found: C, 64.73;
H, 6.02; N, 13.91.
6e: 2, 20-Di(diamylamino)-3, 30-(1, 4-phenylene)bis(3, 5, 6, 7-
tetrahydro-4H-cyclopenta[4,
ones).
5]thieno[2,
3-d]pyrimidin-4-
White crystals (yield 41%). mp: 220.3–220.4ꢀC. 1H
NMR (CDCl3, 600 MHz) d (ppm): 7.40 (s, 4H, Ar-H), 3.01–
1.12 (m, 44H, 22CH2), 0.87–0.84 (t, J = 7.2 Hz, 12H, 4CH3).
13C NMR (CDCl3, 150 MHz) d (ppm): 168.7, 159.2, 154.2,
140.1, 137.1, 134.2, 129.1, 114.3, 51.1, 29.4, 29.2, 28.9, 27.7,
27.1, 22.2, 13.9. MS m/z (%):768 (M+, 70). Anal. Calcd for
C33H38 N6O2 S2: C, 64.47; H, 6.23; N, 13.67; Found: C, 64.76;
H, 5.99; N, 13.93.
[9] Liu, M. G.; Zhong, Y.; Ding, M. W. Chem Res Chinese U
2008, 24, 437.
[10] Vazquez, D.; Peinador, C.; Quintela, J. M. Tetrahedron, 2004,
60, 275.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet