Synthesis, characterisation and antimicrobial activity of thiazole, bisthiazole, pyridone and bispyridone derivatives

Article abstract of DOI:10.3184/030823410X12812857779516

N-cyclohexyl-2-cyano-acetamide was reacted with phenyl isothiocyanates and sulfur to give thiazolidine and bisthiazolidine derivatives. Treatment of N-cyclohexyl-2-cyanoacetamide with phenyl isothiocyanate and KOH followed by in situ heterocyclisation with a-halo compounds gave thiazole derivatives. Treatment of N-cyclohexyl-2-cyanoacetamides with cinnamonitriles gave pyridone and bispyridone derivatives. N-cyclohexyl-2-cyanoacetamide coupled smoothly with benzene-diazonium chloride in pyridine. Cyclocondensation of N-cyclohexyl-2-cyanoacetamide with acetylacetone gave 1,1'-(ethane-1,2-diyl) bis(4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile). Ternary condensation of N-cyclohexyl-2-cyanoacetamide, malononitrile and acetaldehyde gave a bispyridone derivative. Some of the new compounds were tested against bacteria and some fungi.

Full text of DOI:10.3184/030823410X12812857779516

JOURNAL OF CHEMICAL RESEARCH 2010
RESEARCH PAPER 459
AUGUST, 459–464
Synthesis, characterisation and antimicrobial activity of thiazole,
bisthiazole, pyridone and bispyridone derivatives
Gameel A. M. El-Hag Ali, Mohamed H. Helal*, Yehia A. Mohamed, Ahmed A. Ali and
Yousry A. Ammar
Chemistry Department, Faculty of Science, Al-Azhar University, 11284 Nasr City, Cairo, Egypt
N-cyclohexyl-2-cyano-acetamide was reacted with phenyl isothiocyanates and sulfur to give thiazolidine and bisthia-
zolidine derivatives. Treatment of N-cyclohexyl-2-cyanoacetamide with phenyl isothiocyanate and KOH followed
by in situ heterocyclisation with α-halo compounds gave thiazole derivatives. Treatment of N-cyclohexyl-2-cyano-
acetamides with cinnamonitriles gave pyridone and bispyridone derivatives. N-cyclohexyl-2-cyanoacetamide cou-
pled smoothly with benzene-diazonium chloride in pyridine. Cyclocondensation of N-cyclohexyl-2-cyanoacetamide
with acetylacetone gave 1,1’-(ethane-1,2-diyl)bis(4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile). Ternary
condensation of N-cyclohexyl-2-cyanoacetamide, malononitrile and acetaldehyde gave a bispyridone derivative.
Some of the new compounds were tested against bacteria and some fungi.
Keywords: thiazole, bisthiazole, pyridone and bispyridone derivatives, antimicrobial activity
Heterocyclic compounds play an important role in all spheres
of life including pharmaceuticals, natural resources, veteri-
nary, agricultural products analytical reagents and dyes.1,2
Cyanoacetamide derivatives are highly reactive reagents and
their use in heterocyclic synthesis has recently received con-
siderable attention.3–5 The development of effective therapeutic
agents for the treatment of inflammation continues to be a
challenge in medicinal chemistry. Compounds containing thia-
zole have been reported to exhibit anti-inflammatory activ-
ity.6–11 Furthermore, the antimicrobial activity of thiazoles
is well documented.12,13 On the other hand, the synthesis of
polyfunctionalised pyridines is important because of their
widespread occurrence in nature.14–16 The pyridine ring is a
basic unit of numerous biologically active alkaloids and phar-
maceutical products.17,18 Oligopyridines and their complex-
ation with metal ions have been extensively studied because
of their application in coordination and super molecular
chemistry.19,20 Some bipyridine derivatives are used in cataly-
sis, molecular electronics, photoactivated species, and as
optoelectronic devices.21–24
on treatment with ethyl chloroacetate 5a at room temperature
gave the novel 4-thiaozlidinone derivative 6 in good yield.
Cycloalkylation of the intermediate 4 with chloroacetone 5b
at room temperature gave the corresponding 4-methyl thiazole
7 and the structure of thiophene derivative 8 was rejected
according to the spectral data (Scheme 1). The structure of
4-thiazolidinone 6 and 4-methylthiazole 7 derivatives were
elucidated on the basis of elemental analysis and spectral
data.
The reaction of N-cyclohexyl-2-cyanoacetamide 1a with
triethyl orthoformate in acetic anhydride gave N-(cyclohexyl)-
2-ethoxymethylidene-2-cyanoacetamide 9 (Scheme 2). As a
part of this research, the reaction of compound 1a with α-
cyanocinnamonitrile was investigated. Thus, Michael addition
of cyanoacetamide derivative 1a on the activated double bond
of α-cyano-o-chlorocinnamonitrile gave 2-pyridone derivative
13 (Scheme 2). The formation of 2-pyridone 13 proceed via
Michael type addition of the methylene function of 1a to the
activated double bond in α-cyanocinnamonitrile to yield
Michael adduct 10 which underwent intramolecular cyclisa-
tion and auto-oxidation to give 13 (Scheme 2). Structure 13
was established on the basis of spectral data.
Attention has been increasingly paid to the synthesis of
bisheterocyclic compounds, which displayed much better anti-
bacterial activity than heterocyclic compounds.26 Thus, com-
pound 1b coupled smoothly with benzene diazonium chloride
in pyridine to give 2,2p-[ethane-1,2-diylbis(azanediyl)]bis
(2-oxo-N’-phenylacetohydrazonoyl cyanide) 14 (Scheme 3
and Fig. 2)).
Cyclocondensation of compound 1b with acetylacetone
gave 1,1p-(ethane-1,2-diyl)bis(4,6-dimethyl-2-oxo-1,2-dihy-
dropyridine-3-carbonitrile) 16, via intramolecular heterocycli-
sation of the non-isolable intermediate 15 by loss of water.27
Ternary condensation of biscyanoacetamide derivative 1b,
malononitrile and acetaldehyde (1:2:2 molar ratio) in ethanol
solution containing a catalytic amount of piperidine gave bis-
pyridone 17. Similarly, bispyridone 18 was obtained via reac-
tion of compound 1b with α-cyano-p-methylcinnamonitrile
in refluxing ethanol in presence of a catalytic amount of piper-
idine (Scheme 3). The structures of bispyridine derivatives
16–18 were confirmed on the basis of elemental analysis and
spectral data (see Fig. 3).
Encouraged by the above finding, the present investigation
deals with the synthesis of compounds having thiazole,
bisthiazole, pyridine and bispyridine moieties in order to
investigate their antimicrobial activities.
Combination of NH–C=O and CH2CN in N-alkyl-2-
cyanoacetamide molecule opens synthetic opportunities for
further reaction and utilisation as a starting material in the syn-
thesis of many heterocyclic compounds. Therefore N-alkyl-2-
cyanoacetamide derivatives 1a,b were prepared in high yield
from the reaction of aliphatic amines with ethyl cyanoacetate.25
The reactivity of the methylene group in 1a towards isothio-
cyanates and sulfur in the presence of triethylamine was inves-
tigated. Thus, the reaction of N-cyclohexyl-2-cyano-acetamide
1a with isothiocyanate derivatives and/or biphenyl isothiocya-
nate and sulfur in ethanol catalysed with triethylamine
gave thiazolidine and bisthiazolidine derivatives 2a,b and 3
(Scheme 1). The structures of compounds 2a,b and 3 were
established on the basis of analytical analysis and spectral data
(see Fig.1).
The reactivity of the methylene group in cyanoacetamide
derivative 1a towards isothiocyanate in the presence of potas-
sium hydroxide followed by in situ heterocyclisation with
α-halocarbonyl compounds was studied. Thus, the reaction of
cyanoacetamide derivative 1a with phenyl isothiocyanate in
the presence of potassium hydroxide at room temperature gave
the non-isolable potassium salt 4. The potassium sulfide salt 3
Antimicrobial activity
Most of the synthesised compounds were screened for their
antimicrobial activity. The diameter of inhibition zone was
measured as an indicator for the activity of the compounds;
ampillicin is used as reference drug.
* Correspondent. E-mail: m_h_helal_chem@yahoo.com

460 JOURNAL OF CHEMICAL RESEARCH 2010
Scheme 1
Fig. 1 Fragmentation pattern of 2a.
The results for antibacterial activities depicted in Table 1
revealed that compounds 2a, 6, 13, 14, and 18 exhibited good
activities against the reference chemotherapeutics, while com-
pounds 2b, 3, 7 and 16 showed moderate antibacterial activity.
On the other hand, most of the prepared compounds exhibited
moderate antifungal activities against the reference drugs,
whereas, 2a, 6, 9, 16 and 18 exhibited good antifungal activi-
ties against Fusariumoxy sporum and low activity against
Aspergillus ochraceus.
In conclusion, we have described a simple and convenient
route for the synthesis of some heterocyclic bases on thiazole,
bisthiazole, pyridine, and bispyridine derivatives for antimi-
crobial evaluation.
The tested compounds were evaluated by the agar diffusion
technique28 using a 1 mg mL−1 solution in DMSO. The test
organisms were four bacterial strains: Bacillius theringiensis,
Serratia marcescens, Klebsiella pneumoniae, and Proteus
mirabilis and two fungi: Fusarium oxysporum, and Aspergillus
ochraceus. A control using DMSO without the test compound
was included for each organism. Ampicillin was purchased in
Egypt and used in a concentration 2 mg mL−1 as a reference
drug. The bacterial and fungi were tested on nutrient agar and
potato dextrose agar media, respectively. Three plates were
used for each compound as replicates. The plates were incu-
bated for 24 h, and seven days for bacteria and fungi, respec-
tively. After the incubation period, the diameter of inhibition

JOURNAL OF CHEMICAL RESEARCH 2010 461
Scheme 2
1630 cm−1 (C=O). 1H NMR (DMSO-d6): δ =1.21–1.31 (m, 6H, cyclo-
hexyl protons), 1.37 (t, 3H, CH3),1.53–1.72 (m, 4H, cyclohexyl
protons), 3.71 (hump, 1H, cyclohexyl proton), 4.08 (q, 2H, CH2), 6.70
(s, 2H, NH2; exchangeable with D2O), 7.07–7.29 (m, 5H, ArH+ NH;
exchangeable with D2O).13C NMR (DMSO-d6): δ = 24.92, 25.10,
32.35, 47.96, 83.57, 129.81, 129.85, 134.95, 150.72, 160.88, 185.01.
MS: m/z = 376 (M-1; 50%), 332 (75%), 235 (100%), 161 (98%). Anal.
Calcd For C18H23N3O2S2 (377.52): C, 57.27; H, 6.14; N, 11.13. Found:
C, 57.20; H, 6.00; N, 11.10%.
3,3p-(Biphenyl-4,4p-diyl)bis(4-amino-N-cyclohexyl-2-thioxo-2,3-
dihydrothia-zole-5-carboxamide) (3): A mixture of compound 1a
(0.02 mol), biphenylisothio-cyanate (0.01 mol) and elemental sulfur
(0.02 mol) in ethanol (30 mL) containing few drops of triethylamine
were refluxed for 3h, The solid product which produced on heating
was collected by filtration. 60% yield; brown crystals (acetic acid),
m.p. 280–282°C. IR (KBr): ν = 3258 (NH), 2931 (stretching CH) and
1639 cm−1 (C=O).1H NMR (DMSO-d6): δ =1.22–1.26 (m, 6H, cyclo-
hexyl protons), 1.63–1.74 (m, 4H, cyclohexyl protons), 3.72 (hump,
1H, cyclohexyl proton),6.82 (s, 4H, 2NH2; exchangeable with D2O),
7.36–8.00 (m, 10H, ArH and 2NH; exchangeable with D2O). Anal.
Calcd for C32H36N6O2S4 (664.93): C, 57.80; H, 5.46; N, 12.64. Found:
C, 57.60; H, 5.30; N, 12.60%.
zone was measured as an indicator for the activity of the
compounds.
Experimental
All melting points are uncorrected. IR spectra (KBr) were measured
1
on Shimadzu 440 spectrometer, H NMR spectra were obtained in
DMSO on a Varian Gemini 200 MHz spectrometer using TMS as
internal standard; chemical shifts are reported as (ppm). Mass spectra
were obtained on GCMS\QP 1000 Ex mass spectrometer at 70 eV.
Elemental analyses were carried out at the Microanalytical Center,
Faculty of Science (Cairo University, Egypt). Microbiology screening
was carried out in the Botany Department, Faculty of Science,
Al-Azhar University.
Synthesis of dihydrothiazole derivatives (2a,b)
A mixture of compound 1a (0.01 mol), the requisite aryl isothiocya-
nate (0.01 mol) and elemental sulfur (0.01 mol) in ethanol (30 mL)
containing few drops of triethylamine were refluxed for 3h, the solid
product so formed on heating was collected and recrystallised from
suitable solvent to give 2a,b.
4-Amino-N-cyclohexyl-3-phenyl-2-thioxo-2,3-dihydrothiazole-5-
carboxamide (2a): 70% yield; brown crystals (acetic acid), m.p. 266–
268°C. IR (KBr): ν = 3461, 3301, 3213 (NH and NH2) and 1654 cm−1
Preparation of compounds 6 and 7
1
To a suspension of finely powdered potassium hydroxide (0.01 mol)
in dry dimethylformamide (10 mL), cyanoacetamide derivative (1a)
(0.01 mol) and then the phenyl isothiocyanate (0.01 mol) were added
in portions. The reaction mixture was stirred at room temperature with
α-halocarbonyl compounds (namely, ethyl chloroacetate, chloroace-
tone; 0.01 mol) and left at room temperature for 3h, then it was placed
into ice-water and acidified with 0.1 N HC1 at pH 3–4. The resulting
precipitate was filtered off, dried and recrystallised from the proper
solvent.
(C=O). H NMR (DMSO-d6): δ = 1.24–1.35 (m, 6H, cyclohexyl
protons), 1.57–1.76 (m, 4H, cyclohexyl protons), 3.82 (hump, 1H,
cyclohexyl proton), 6.50 (s, 2H, NH2), 6.81–7.42 (m, 5H, ArH), 8.26
(s, 1H, NH). MS: m/z = 333 (M+; 50%), 250 (0.2%), 208 (25%), 136
(40%), 77 (100%). Anal. Calcd for C16H19N3OS2 (333.47): C, 57.63;
H, 5.74; N, 12.60. Found: C, 57.60; H, 5.60; N, 12.55%.
4-Amino-N-cyclohexyl-3-(4-ethoxyphenyl)-2-thioxo-2,3-dihydro-
thiazole-5-carboxamide (2b): 65% yield; brown crystals (acetic acid),
m.p. 266–268°C. IR (KBr): ν = 3332, 3280, 3258 (NH/NH2) and

462 JOURNAL OF CHEMICAL RESEARCH 2010
Scheme 3
Fig. 2 Fragmentation pattern of 14.

JOURNAL OF CHEMICAL RESEARCH 2010 463
Fig. 3 13CNMR of 18.
Table 1 Zone (mean diameter of inhibition in mm) as a criterion of antibacetrial and antifungal activities of the newly synthesised
compounds
Compound
Bacteria
Fungi
Bacillius
theringiensis
Serratia
marcescens
Klebsiella
pneumoniae
Proteus
mirabilis
Fusarium
oxysporum
Aspergillus
ochraceus
2a
13
27.55
21
15
6
33
22
24
31
11
19
31
27
24
31
40
14.5
7
3
4
2b
11.5
10.5
15
3
21
12
17
11
15
16
16.5
14
17
20
9
2
6
28
13
5
14
6
7
13
14
15
–
7
12
21
5
9
9
9
1
13
15
26.5
26.5
22
3
14
13.5
10
3
16
2
18
16
17
31
40
–
Ampicillin
10
2-Cyano-N-cyclohexyl-2-(4-oxo-3-phenylthiazolidin-2-ylidene)
acetamide (6): 70% yield; brown crystals (benzene), m.p. 270–272°C.
IR (KBr): ν = 3332 (NH), 2189 (C≡N) and 1684, 1640 cm−1 (C=O). 1H
NMR (DMSO-d6): δ = 1.34–1.47 (m, 6H, cyclohexyl protons), 1.57–
1.77 (m, 4H, cyclohexyl protons), 3.74 (hump, 1H, cyclohexyl proton),
4.02 (s, 2H, CH2), 7.16–7.31 (m, 5H, ArH), 9.37 (s, 1H, NH). MS:
m/z = 341 (M+; 25.6%), 284 (30.3%), 250 (26.7%), 172 (73.6%),
76 (100%). Anal. Calcd for C18H19N3O2S (341.43): C, 63.32; H, 5.61;
N, 12.31. Found: C, 63.33; H, 5.50; N, 12.25%.
2-Cyano-N-cyclohexyl-2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)
acetamide (7): 60% yield; brown crystals (benzene), m.p. 185–187°C.
IR (KBr): ν = 3219, 3105 (NH), 2923 (aliph. CH), 2164 (C≡N) and
1635 cm−1 (C=O). 1H NMR (DMSO-d6): δ =1.16–1.21 (m, 6H, cyclo-
hexyl protons), 1.63–1.67 (m, 4H, cyclohexyl protons), 1.79 (s, 3H,
CH3), 3.53 (hump, 1H, cyclohexyl proton), 6.21 (d, 1H, NH), 6.80 (s,
1H, thiazol-H5), 7.46–7.57 (m, 5H,ArH). MS: m/z = 339 (M+; 49.2%),
241 (85.8%), 128 (23%), 93 (50%), 55 (100%). Anal.Calcd for
C19H21N3OS (339.45): C, 67.23; H, 6.24; N, 12.38. Found: C, 67.22;
H, 6.10; N, 12.30%.
derivative 1a (0.01 mol) and few drops of piperidine and the reaction
mixture was heated under reflux for 2h, then left to cool to room tem-
perature. The precipitated product was collected by filtration, and
recrystallised from acetic acid as yellow crystals. 65% yield, m.p.
>300°C. IR (KBr): ν = 3458, 3288 (NH2), 2938 (stretching CH), 2213
1
(C≡N), and 1644 cm−1 (C=O). H NMR (DMSO-d6): δ =1.16–1.34
(m, 6H, cyclohexyl protons), 1.55–1.73 (m, 4H, cyclohexyl protons),
3.71 (hump, 1H, cyclohexyl proton), 7.12–7.63 (m, 6H, ArH+ NH2).
MS: m/z = 352 (M+; 24.3%), 270 (75%), 245 (8%), 180 (10%), 68
(47%), 55 (100%). Anal. Calcd For C19H17N4OCl (352.82): C, 64.68;
H, 4.86; N, 15.88. Found: C, 64.60; H, 4.80; N, 15.80%.
2,2p-(Ethane-1,2-diylbis(azanediyl))bis(2-oxo-Np-phenylacetohy-
drazonoyl cyanide) (14): A mixture of compound 1b (0.01 mol), ben-
zene diazonium chloride (0.02 mol) and pyridine (10 mL) was stirred
at room temperature for 6 h. The resulting solution was poured into
crushed ice with adding a few drops of conc. HCl and the precipitate
product was collected and crystallised from dioxane as red crystals.
70% yield, m.p. 210–213°C. IR (KBr): ν = 3304 (NH), 2922 (CH-
aliph.), 2216 (C≡N), and 1648 cm−1 (C=O). 1H NMR (DMSO-d6): δ =
4.01 (s, 4H, 2CH2), 7.14–7.88 (m, 10H, ArH), 8.11, 9.8 (2s, 4H, 4NH).
MS: m/z = 402 (M+; 23.7%), 298 (30%), 172 (40%), 144 (10.9%),
109 (15%), 77 (100%).Anal. Calcd for C20H18N8O2 (402.41): C, 59.69;
H, 4.51; N, 27.85. Found: C, 59.60; H, 4.40; N, 27.80%.
1,1p-(Ethane-1,2-diyl)bis(4,6-dimethyl-2-oxo-1,2-dihydropyridine-
3-carbonitr-ile) (16): Equimolar amounts of 1b (0.01 mol) and acety-
lacetone (excess) with a few drops of piperidine in an oil bath were
refluxed for 1 h at 160°C, then allowed to cool. The solid product was
collected and recrystallised from ethanol as yellow crystals to give 16.
70% yield, m.p. 240–243°C. IR (KBr): ν = 3304 (NH), 2922 (stretch-
ing CH), 2216 (C≡N), and 1648cm−1 (C=O).1H NMR (DMSO-d6):
δ = 2.27, 2.50 (s, 12H, 4CH3), 4.24 (s, 4H, 2CH2),6.03 (s, 2H, pyri-
dine-H). MS: m/z = 322 (M+; 15%), 258 (30%), 256 (15%), 218
(17%), 173 (100%), 149 (95%), 104 (20%), and 77 (30%). Anal.
Calcd for C18H18N4O2 (322.36): C, 67.07; H, 5.63; N, 17.38. Found:
C, 67.00; H, 5.20; N, 17.30%.
2-Cyano-N-cyclohexyl-3-ethoxyacrylamide (9): A mixture of 1a
(0.01 mol), triethylorthoformate (0.01 mol) and acetic anhydride
(20 mL) was heated under reflux for 3h. The solid product was
collected and recrystallised from dioxane as white crystals. 75% yield,
m.p. 140–142°C. IR (KBr): ν = 3258 (NH), 2968, 2922 (stretching
1
CH), 2200 (C≡N) and 1661 cm−1 (C=O). H NMR (DMSO-d6): δ =
1.19–1.28 (m, 6H, cyclohexyl protons), 1.39 (t, 3H, CH3), 1.56–1.75
(m, 4H, cyclohexyl protons), 3.84 (hump, 1H, cyclohexyl proton),
4.23 (q, 2H, CH2), 8.15 (s, 1H, methine-H), 8.87 (s, 1H, NH). MS:
m/z = 222 (M+; 0.5%), 199 (8%), 185 (12%), 171 (10%), 157 (10%),
149 (16%), 129 (25%), 115 (15%), 98 (33%), 97 (38%), 73 (47%),
55 (100%). Anal. Calcd for C12H18N2O2 (222.28): C, 64.84; H, 8.16;
N, 12.60. Found: C, 64.80; H, 8.00; N, 12.50%.
6-Amino-4-(2-chlorophenyl)-1-cyclohexyl-2-oxo-1,2-dihydropyridine-
3,5-dicarbonitrile (13): To a solution of o-chlorobenzylidenemalono-
nitrile (0.01 mol) in ethanol (30 mL) was added cyanoacetamide

464 JOURNAL OF CHEMICAL RESEARCH 2010
5
6
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1,1p-(Ethane-1,2-diyl)bis(6-amino-4-Methyl-2-oxo-1,2-dihydropyri-
dine-3,5-dicarbonitrile) (17): A mixture of biscyanoacetanilide 1b
(0.01 mol), acetaldehyde (0.02 mol), malononitrile (0.02 mol) in etha-
nol (30 mL) containing piperidine (0.5 mL) was heated under reflux
for 3hr. the resulting solid was filtered off and recrystallised from the
suitable solvent to give 17. 70% yield, m.p. 300–302°C. IR (KBr): ν =
1
3333, 3316 (NH2), 2216 (C≡N) and 1642 cm−1 (C=O). H NMR
(DMSO-d6): δ = 2.16 (s, 6H, 2CH3), 4.31 (s, 4H, 2CH2), 6.89 (s, 4H,
2NH2). MS: m/z = 376 (M+2; 15%), 342 (23%), 271 (26%), 163
(45%), 111 (100%), 67 (53%). Anal. Calcd for C18H14N8O2 (374.36):
C, 57.75; H, 3.77; N, 29.93. Found: C, 57.70; H, 3.70; N, 29.90%.
1,1p-(Ethane-1,2-diyl)bis(6-amino-2-oxo-4-p-tolyl-1,2-dihydro-
pyridine-3,5-dicarbonitrile) (18): To a mixture of biscyanoacetanilide
derivative 1b (0.01 mol), p-tolualdehyde (0.02 mol), malononitrile
(0.02 mol) in ethanol (30 mL), piperidine (0.5 mL) was added. The
reaction mixture was refluxed for 4 h. The solid product which
produced on heating was collected and recrystallised from dioxane
as brown crystals. 65% yield, m.p. >300°C. IR (KBr): ν = 3492, 3324
(NH2), 2214 (C≡N), and 1640 cm−1 (C=O).1H NMR (DMSO-d6):
δ = 2.34, 2.37 (2s, 6H, 2CH3),4.40 (s, 4H, 2CH2),7.18–7.41 (m, 8H,
ArH), 8.58 (s, 4H, 2NH2; exchangeable with D2O).13C NMR (DMSO-
d6): δ = 22.96, 40.33, 40.86, 54.67, 115.65, 116.53, 129.11, 120.67,
120.72, 153.93, 162.67 and 163.56. MS: m/z = 526 (M+; 6%), 423
(23%), 368 (21.4%), 360 (40%), 273 (60%), 290 (100%), 189 (55%),
143 (40%), 84 (72%). Anal. Calcd For C30H22N8O2 (526.55): C, 68.43;
H, 4.21; N, 21.28. Found: C, 68.40; H, 4.10; N, 21.20%.
8
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Received 9 May 2010; accepted 12 July 2010
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