A simple synthesis of some new thienopyridine and thieno-pyrimidine derivatives

Article abstract of DOI:10.3390/71000756

A number of pyridothienopyridine (2, 3), pyridothienopyrimidine (6, 10), pyridothienotriazine (13), pyrimidothienopyrimidine (15, 16, 17a,b) and thienoimidazo-triazines (18) were obtained via interaction of 3-amino-5-phenylamino-2,4-dicarbonitrile (1) with different reagents.

Full text of DOI:10.3390/71000756

Molecules 2002, 7, 756-766
molecules
ISSN 1420-3049
http://www.mdpi.org
A Simple Synthesis of Some New Thienopyridine and Thieno-
pyrimidine Derivatives
*
Ahmed M. M. El-Saghier
Department of Chemistry, Faculty of Science, South Valley University, Sohag 82524, Egypt.
Tel. (+20) 106393441, Fax. (+20) 93602054
*Author to whom correspondence should be addressed; e-mail: el_saghier@yahoo.com
Received: 8 May 2002; in revised form: 25 August 2002 / Accepted: 18 September 2002 / Published:
31 October 2002
Abstract: A number of pyridothienopyridine (2, 3), pyridothienopyrimidine (6, 10),
pyridothienotriazine (13), pyrimidothienopyrimidine (15, 16, 17a,b) and thienoimidazo-triazines
(18) were obtained via interaction of 3-amino-5-phenylamino-2,4-dicarbonitrile (1) with
different reagents.
Keywords:
pyridothienopyridines,
pyridothienopyrimidines,
thienotriazopyrimidines,
pyridothienotriazines, pyrimidothienopyrimidines.
Introduction
Many thienopyridines have been evaluated pharmacologically and have been found to show activity
against, for example, diabetes mellitus [1-3], as analgesics and antiinflammatories [4-6], sedatives [4],
anticoagulants [6], antiartherosclerotics [7], and as gonadotropin releasing hormone antagonists [8].
Moreover the pyridothienopyrimidines showed analgesic and antiinflammatory activity [9].
In earlier communications, we have reported the syntheses and reactions of various thiophenes and fused
thiophenes [10-12], which were prepared in one-pot reactions using phase transfer techniques (PTC). Also,
several papers have reported the synthesis of polyfused heterocycles containing different nuclei [13-16],
starting from fused thiophenes prepared in our laboratory.

Molecules 2002, 7
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Results and Discussion
We report herein the synthesis of some new polyfunctionally substituted thienopyridines,
thienopyrimidines and pyridothienopyrimidines starting with 3-amino-5-phenylamino-2,4-dicarbonitrile (1).
Compound 1 was prepared in one-pot reaction using PTC conditions [K2CO3/benzene/ tetrabutylammonium
bromide (TBAB)] from malononitrile, PhNCS and ClCH2CN compounds in a 1:1:1 molar ratio, (Scheme 1)
[12].
Scheme 1
NC
NH2
NC
PTC
CN
PhNCS
ClCH CN
+
+
2
PhHN
CN
S
1
Compound 1 was allowed to react with two moles of ethyl cyanoacetate or diethyl malonate in the
presence of ammonium acetate-acetic acid at 200oC [17] to give the corresponding 4,9-diamino-2,7-dioxo-
6-phenyl-1,2,6,7-tetrahydropyrido[2',3':4,5]thieno[2,3-b]pyridin-3,8-dicarbonitrile (2) or 4,9-diamino-3,8-
diethoxycarbonyl-6-phenyl-1,2,6,7-tetrahydro[2',3':4,5]thieno[2,3-b]pyridin-2,7-dione (3).
Scheme 2
O
H
NH2
N
CNCH CO Et
2
2
2
CN
NH2
NC
O
S
N
.
Ph
2
O
H
NH2
N
COOEt
NH2
EtOOC
O
CH (CO Et)
2
2
2
2
S
N
P.h
3
NC
N
NC
NH2
NC
N
HCONH2
PhCHO
N
N
PhHN
PhHN
CN
PhHN
S
S
S
NH2
N=CHPh
5
4
1
.
.
NCCH2CO2Et
NH2
NC
N
N
N=CHPh
O
N
Ph
S
.
6

Molecules 2002, 7
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Reaction of compound 1 with formamide gave the corresponding 4-amino-6-phenylamino-thieno[3,2-
d]pyrimidin-7-carbonitrile (4) which was allowed then allowed to react with benzaldehyde to yield 6-
phenylamino-4-benzalaminothieno[3,2-d]pyrimidin-7-carbonitrile
(5).
9-Amino-7-oxo-6-phenyl-4-
phenylmethanimido-6,7-dihydropyrido-[3',2':4,5]thieno[3,2-d]pyrimidin-8-carbonitrile (6) was obtained by
treating compound 5 with ethyl cyanoacetate (Scheme 2).
The condensation of compound 1 with triethyl orthoformate in refluxing acetic anhydride gave ethyl N-
(2,4-dicyano-5-phenylamino-3-yl)metanimidate (7) which underwent further cyclization upon treatment with
hydrazine hydrate at room temperature affording 3-amino-3,4-dihydro-4-imino-6-phenylaminothieno[3,2-
d]pyrimidin-7-carbonitrile (8) (Scheme 3).
Scheme 3
NC
NC
N=CHOEt
CN
N
H2NNH2 .H2O
HC(OEt)3
Ac2O
NH
N
2
PhHN
PhHN
S
S
NH
8
7
HC(OEt)3
Ac2O
NH2
NC
N
NC
N
N
O
N
N
N
N
S
PhHN
N
S
Ph
N
10
1
9
NH2
NC
NC
N
N
N
N
NaNO2/HCl
AcOH
N
N
O
PhHN
S
N
S
Cl
Ph
Cl
11
12
H2NNH2.H2O
NH2
NC
N
N
N
O
N
S
Ph
NHNH2
13

Molecules 2002, 7
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Reaction of compound 8 with triethyl orthoformate gave 8-phenylaminothieno[3,2-d][1,2,4]-triazolo[3,2-
f]pyrimidin-7-carbonitrile (9). Fusion of compound 9 with ethyl cyanoacetate in the presence of ammonium
acetate yielded 7-amino-9-oxo-10-phenyl-9,10-dihydropyrido[3',2':4,5]-thieno[3,2-d][1,2,4]triazolo[3,2-
f]pyrimidin-8-carbonitrile (10). Diazotisation of compound 1 with NaNO2/concentrated HCl led to the
formation of 4-chloro-6-phenylaminothieno[3,2-d]-1,2,3-triazin-7-carbonitrile (11) which, in turn, was
allowed to react with ethyl cyanoacetate to give 9-amino-4-chloro-7-oxo-6-phenyl-6,7-
dihydropyrido[3',2':4,5]thieno[3,2-d][1,2,3]triazin-8-carbonitrile (12). Compound 12 was further treated
with hydrazine hydrate to afford 9-amino-4-hydrazino-7-oxo-6-phenyl-6,7-dihydropyrido-[3',2':4,5]-
thieno[3,2-d][1,2,3]triazin-8-carbonitrile (13).
Incorporation of the imidazolyl moiety in pyrimidothienopyrimidine, imidazothienopyrimidine and
imidazothienotriazine systems were achieved by converting the nitrile group of compound 1 into a
dihydroimidazolyl residue, followed by some additional reactions [18]. Thus, the interaction of compound 1
with ethylenediamine in the presence of carbon disulfide afforded 3-amino-2,4-di(4,5-dihydro-1H-2-
imidazolyl)-5-phenylaminothiophene (14) (Scheme 4).
Scheme 4
S
H2N
NH
N
NH2
NC
NH2
S
H
H
H2N(CH2)2NH2
CS2
NH2
N
S
PhHN
PhHN
CN
S
S
S
NH
1
N
N
NH2
H
H2NSC
PhHN
NH2
H
H2N(CH2)2NH2
heat
N
PhHN
S
CSNH2
S
N
14
Treatment of compound 14 with triethyl orthoformate, benzaldehyde, dimethythiomethylenemalononitrile
or dimethylthio-2-acetylbuten-3-one furnished 5,6,12-triphenyl-2,3,5,6,9,10-hexahydroimidazo[1,2-
c]imidazo[2",1":6',1']pyrimido[4',5':4,5]thieno[3,2-e]pyrimidine (15), 5-ethoxy-6-phenyl-2,3,5,6,-9,10-
hexahydroimidazo[1,2-c]imidazo[2",1":6',1']pyrimido[4',5':4,5]-thieno[3,2-e]-pyrimidine (16), 2-(12-(1,1-
dicyanomethylidene)-6-phenyl-2,3,5,6,9,10,12,13-octahydro-imidazo[1,2-c]imidazo[2",1":6',1']pyrimido-
[4',5':4,5]thieno[3,2-e]pyrimidin-5-yliden)malononitrile (17a) or 2-(12-(1-acetyl-2-oxopropylidene)-6-
phenyl-2,3,5,6,9,10,12,13-octahydroimidazo[1,2-c]imidazo[2",1":6',1']-pyrimido[4',5':4,5]thieno[3,2-

Molecules 2002, 7
760
e]pyrimidin-5-yliden)-2,4-pentandione (17b), respectively. In addition 7-(4,5-dihydro-1H-2-imidazolyl)-
2,3-dihydro-8-phenylaminoimidazo[1,2-c]-thieno[2,3-e][1,2,3]-triazine (18) was obtained through the
treatment of compound 14 with nitrous acid (Scheme 5). Analytical and spectral data of the newly
synthesized compounds were in agreement with the proposed structures (Tables 1 and 2).
Scheme 5
N
Ph
PhCHO
N
N
N
Ph
N
S
N
Ph
15
N
HC(OEt)3
N
N
N
EtO
N
S
N
Ph
N
16
N
H
NH2
X
X
X
SMe
SMe
N
H
N
X
N
PhHN
N
S
X
N
N
14
N
S
X
N
Ph
17a,b
a,X=CN
b,X=COCH3
N
N
N
N
H
N
NaNO2/HCl
H
N
S
N
Ph
18
Experimental
General
All melting points were determined on a Koffler melting points apparatus and are uncorrected. IR spectra
were obtained on a Nicolet 710 FT-IR spectrometer. 1H-NMR spectra were recorded on a Varian EM 360
A at 60 MHz using TMS as an internal reference. Elemental analyses were carried out with an elemental

Molecules 2002, 7
761
analyzer model 240 C. Satisfactory microanalysis (C±0.4, H±0.4, N±0.3%) were obtained for all newly
prepared compounds.
4,9-diamino-2,7-dioxo-6-phenyl-1,2,6,7-tetrahydropyrido[2',3':4,5]thieno[2,3-b]pyridin-3,8-dicarbo-
nitrile (2) or 4,9-diamino-3,8-diethoxycarbonyl-6-phenyl-1,2,6,7-tetrahydro[2',3':4,5]-thieno[2,3-
b]pyridin-2,7-dione (3). A mixture of 1 (0.01 mol), ethyl cyanoacetate or diethyl malonate (0.02 mol),
ammonium acetate (6 g) and acetic acid (1.2 mL) was heated with stirring at 200 oC for 2h, left to cool and
then triturated with ethanol. The solid product thus formed was collected by filtration. Compound 2 (from
o
ethyl cyanoacetate) was recrystallized from ethanol as yellow needles; m. p. 200 C. Compound 3 (from
diethyl malonate) was recrystallized from ethanol as orange crystals; m. p. > 320 oC.
4-Amino-6-phenylaminothieno[3,2-d]pyrimidin-7-carbonitrile (4). A solution of 1 (0.001 mol) in
formamide (10 mL) was refluxed for 2h. The precipitate that formed on cooling was filtered off and
recrystallized from ethanol to give white powder; m.p. >271 oC.
6-Phenylamino-4-benzalaminothieno[3,2-d]pyrimidin-7-carbonitrile (5). An equimolar mixture of 4
(0.01 mol) and benzaldehyde (0.01 mol) was dissolved in EtOH (30 mL) in the presence of a few drops of
piperidine. The reaction mixture was refluxed for 2h and left to cool. The solid product was filtered off and
recrystallized from pyridine as white crystals; m.p. 243 oC.
General Procedure for the Preparation of Thienopyridone Derivatives 6, 10 or 12. A mixture of 1 (0.01
mol), ethyl cyanoacetate (0.01 mol), ammonium acetate (3 g) and acetic acid (0.6 mL) was heated with
stirring at 200 oC for 2h, then left to cool and triturated with ethanol. The solid product, so formed, was
collected by filtration and recrystallized from appropriate solvents.
9-Amino-7-oxo-6-phenyl-4-phenylmethanimido-6,7-dihydropyrido[3',2':4,5]thieno[3,2-d]-pyrimidin-8-
carbonitrile (6). Recrystallized from pyridine as white crystals; m.p. 220 oC.
7-Amino-9-oxo-10-phenyl-9,10-dihydropyrido[3',2':4,5]thieno[3,2-d][1,2,4]triazolo-[3,2-f]-
pyrimidin-8-carbonitrile (10). Recrystallized from acetonitrile as yellow crystals; m.p. 236 oC.
9-Amino-4-chloro-7-oxo-6-phenyl-6,7-dihydropyrido-[3',2':4,5]thieno[3,2-d][1,2,3]triazin-8-carbo-
nitrile (12). Recrystallized from acetonitrile as yellow crystals; m.p. 158-160 oC.
Ethyl N-(2,4-dicyano-5-phenylamino-3-yl)metanimidate (7). A mixture of 1 (0.005 mol), triethyl
orthoformate (3 mL) and acetic anhydride (20 mL) was heated under reflux for 5h. After cooling the
precipitated solid was filtered off and recrystallized from ethanol as white crystals; m.p. 215 oC.

Molecules 2002, 7
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3-Amino-3,4-dihydro-4-imino-6-phenylaminoyhieno[3,2-d]pyrimidin-7-carbonitrile (8). Hydrazine
hydrate (80%) (4 mL) was added to a suspension of 7 (0.005 mol) in dioxane (40 mL). The reaction mixture
was stirred at room temperature for 1h. The precipitate which formed was filtered off, washed with water,
dried in air and recrystallized from dioxane as white crystals; m.p. 185 oC.
8-Phenylaminothieno[3,2-d][1,2,4]triazolo[3,2-f]pyrimidin-7-carbonitrile (9). Compound 8 (0.001
mol) in an excess of triethyl orthoformate (7 mL) was refluxed for 1h. After cooling, the precipitated product
was collected by filtration and recrystallized from ethanol-chloroform mixture as white needles; m.p. 299 oC.
4-Chloro-6-phenylamino-thieno[3,2-d]-1,2,3-triazin-7-carbonitrile (11). A solution of (0.01 mol) sodium
nitrite in 10 mL of water was added to a cold solution of 1 (0.005 mol) in acetic acid (30 mL) and
concentrated hydrochloric acid (15 mL). After completion of the addition, the ice bath was removed and
stirring continued for an additional 2h. The crude product obtained was recrystallized from ethanol as white
needles; m.p. 201 oC.
9-Amino-4-hydrazino-7-oxo-6-phenyl-6,7-dihydropyrido-[3',2':4,5]thieno[3,2-d][1,2,3]triazin-8-
carbonitrile (13). A mixture of 12 (0.002 mol) and hydrazine hydrate (3 mL) in ethanol (20 mL) was
refluxed for 1h. The precipitate that separated after cooling was recrystallized from dioxane as white crystals;
m.p. 262 oC.
3-Amino-2,4-di(4,5-dihydro-1H-2-imidazolyl)-5-phenylaminothiophene (14). To a suspension of 1
(0.002 mol), ethylenediamine (3 mL) and carbon disulfide (1 mL) were added dropwise. The reaction
mixture was heated on a water bath for 2h. The precipitated solid was triturated with ethanol (10 mL), filtered
off and recrystallized from ethanol to give golden yellow crystals; m.p. 197 oC.
5,6,12-Triphenyl-2,3,5,6,9,10-hexahydroimidazo[1,2-c]imidazo-[2",1":6',1']pyrimido[4',5':4,5]-
thieno-[3,2-e]pyrimidine (15). A mixture of 14 (0.005 mol), benzaldehyde (0.01 mol) and acetic acid (15
mL) was heated under reflux for 5 h. The precipitated solid was collected and recrystallized from dioxane in
the form of white needles; m.p. 215 oC.
5-Ethoxy-6-phenyl-2,3,5,6,-9,10-hexahydroimidazo[1,2-c]imidazo[2",1":6',1']pyrimido[4',5':4,5]-
thieno[3,2-e]pyrimidine (16). Compound 14 (0.001 mol) in triethyl orthoformate (14 mL) was heated
under reflux for 3 h. The precipitated solid was collected and recrystallized from pyridine as pale yellow
crystals; m.p. 163 oC.
Preparation of 2-(12-(1,1-dicyanomethylidene)-6-phenyl-2,3,5,6,9,10,12,13-octahydroimidazo[1,2-
c]imidazo[2",1":6',1']pyrimido[4',5':4,5]thieno[3,2-e]pyrimidin-5-yliden)malononitrile (17a) and 2-
(12-(1-Acetyl-2-oxopropylidene)-6-phenyl-2,3,5,6,9,10,12,13-octahydroimidazo[1,2-c]imidazo-[2",1":
6',1']pyrimido[4',5':4,5]thieno[3,2-e]pyrimidin-5-yliden)-2,4-pentandione (17b). A mixture of 1 (0.001

Molecules 2002, 7
763
mol) and dimethylthiomethylenemalononitrile or 2-acetyl-1,1-dimethylthiobuten-3-one (0.002 mol) in ethanol
(20 mL) was heated under reflux for 24h. The separated solids were collected and recrystallized from the
o
appropriate solvent. Compound 17a: gray crystals; m.p. 172 C (from dioxane). Compound 17b: orange
crystals; m.p.179 oC (from methanol).
7-(4,5-Dihydro-1H-2-imidazolyl)-2,3-dihydro-8-phenylaminoimidazo[1,2-c]thieno[2,3-e][1,2,3]-
triazine (18). To a solution of 1 (0.001 mol) in concentrated sulphuric acid (2 mL) and glacial acetic acid (10
mL), sodium nitrite (0.003 mol) dissolved in 5 mL water was added dropwise with constant stirring during 10
minutes. The mixture was stirred without heating for additional 1 h and then diluted with water. The forming
precipitate was filtered off and recrystallized from ethanol as white needles; m.p. 269 oC.
Table 1: Analytical data for the newly prepared compounds
Yield
%
Mol.Form.
Mol. Wt.
C18H10N6O2S
374.37
Analysis(%) Calcd./Found
Product
C
H
N
S
76
57.75
57.64
56.40
56.48
58.41
58.56
67.58
67.67
65.38
65.44
60.82
61.02
55.30
55.22
57.52
57.33
56.81
56.77
50.10
49.99
2.67
2.73
4.27
4.05
3.63
3.55
3.66
3.77
3.31
3.23
4.05
3.98
3.54
3.46
2.74
2.87
2.50
2.56
2.09
1.98
22.44
22.55
17.93
17.85
26.28
25.99
19.69
19.58
19.88
19.92
18.90
19.03
29.75
29.66
28.74
28.65
27.27
27.30
24.33
24.15
8.56
2
8.62
81
92
85
77
89
90
78
66
75
C22H20N4O6S
468.48
6.83
3
4
6.77
C13H9N5S
267.30
11.97
11.88
9.00
C20H13N5S
355.41
5
8.98
C23H14N6 OS
422.46
7.57
6
7.61
C15H12N4OS
269.21
10.82
1076
11.33
11.43
11.94
11.99
8.90
7
C13H10N6S
282.32
8
C14H8N6S
292.31
9
C17H9N7OS
359.36
10
11
9.12
C12H6N5SCl
287.72
11.12
10.98

Molecules 2002, 7
764
81
64
91
89
78
85
82
89
C15H7N6OSC
354.77
50.77
50.85
51.42
51.61
58.87
58.84
71.97
71.89
61.20
60.32
60.75
60.56
61.97
62.13
56.95
57.02
1.97
2.01
2.85
2.82
5.61
5.54
4.79
4.81
5.10
4.94
2.95
3.02
4.79
4.81
4.44
4.32
23.68
23.44
31.97
31.99
25.73
25.62
211.40
21.32
21.40
21.22
22.50
22.65
15.48
15.50
29.04
30.12
9.02
8.94
9.13
8.99
9.80
9.91
6.39
6.41
8.15
8.00
6.74
6.61
5.89
5.75
9.48
9.51
12
13
C15H10N8OS
350.35
C16H18N6S
326.41
14
C30H24N6S
500.62
15
C20H20N6OS
392.47
16
C24H14N10S
474.50
17a
17b
18
C28H26N6O4S
542.61
C16H15N7S
337.40
Table 2: Spectroscopic data of the newly prepared compounds.
IR (KBr)b 1H-NMRc (DMSO-d6)
Product
3430,3330,3300 (2NH2), 3180 (NH), 8.20 (s,1H,NH), 7.70-7.20 (m,5H,arom.), 6.20-5.90
2222, 2210 (2CN), 1640, 1630 (C=O) (br,2H,NH2)
2
3
4
5
6
7
8
9
3420,3300,3250(2NH2), 3190 (NH), 8.30-7.80 (m,5H,arom.), 6.30-6.10 (br,2H,NH2 ), 4.80-
1720,1710 (C=O ester), 1630 (C=O).
4.60 (br,2H,NH2), 2.80 (s,3H,COCH3) , 2.10 (s,3H,CH3).
3340,3300, (NH2), 3200 (NH), 2218 9.10 (s,1H,NH), 8.40 (s,1H,CH-Pyridine), 7.70-7.20
(CN).
(m,5H,arom.), 5.50 (s,2H,NH2).
3200(NH), 2210 (CN).
9.10 (s,1H,NH), 8.40 (s,1H,CH-Pyridine), 7.90-7.30
(m,10H,arom.), 5.50-5.10 (br,2H,NH2).
3350,3240 (NH2), 2220 (CN), 1640 8.40 (s,1H,CH-Pyridine), 8.10 (s,1H,N=CH), 7.90-7.00
(C=O). (m,10H,arom.), 6.20 (s,2H,NH2).
3180 (NH), 2220,2210 (CN), 1630 8.50 (s,1H,NH), 7.70 (s,1H,CH), 7.70-7.00 (m,5H,arom.),
(C=N). 3.80-3.40 (q,2H,OCH2), 1.25-1.00 (t,3H,CH3).
3430,3330 (NH2), 3200,3180 (2NH), 8.20-8.00 (br,2H,2NH), 7.80 (s,1H,CH), 7.70-7.20
2190 (CN). (m,5H,arom.), 5.20 (s,2H,NH2).
3180 (NH), 2220 (CN), 1600 8.80 (s,1H,NH), 8.40 (s,1H,CH-Pyridine), 8.10 (s,1H,CH-
(C=N). triazole), 7.50-7.00 (m,5H,arom.), 6.20 (s,2H,NH2).

Molecules 2002, 7
765
3400, 3330, 3300 (2NH2), 2217 8.50 (s,1H,CH-Pyridine), 8.20 (s,1H,CH-triazole), 7.50-
10
(CN), 1640 (C=O), 1600 (C=N).
7.00 (m,5H,arom.), 6.20 (s,2H, NH2).
8.40 (s,1H,NH), 7.70-7.20 (m,5H,arom.).
3320 (NH), 2210 (CN), 1640 (C=N).
11
12
3340,3300, 3270(2NH2), 2220 (CN), 7.70-7.00 (m,5H,arom.), 6.20-6.00 (br,2H, (NH2).
1640(C=O), 1620(C=N).
3350,3330,3210
(2NH2),
3180, 8.00 (s,1H,NH), 7.80-7.20 (m,5H,arom.), 6.10 (s,2H,NH2),
5.00 (s,2H,NH2).
13
14
(NH), 2220 (CN), 1640 (C=O)
3390,3260 (NH2), 3200,3180,3100 8.40 (s,1H,NH), 8.10 (s,1H,NH), 7.70-7.10 (m,5H,arom.),
(3NH).
5.60 (s,2H,NH2), 4.00-3.50 (m, 8H,4CH2-imidazole).
7.90-7.10 (m,15H,arom.), 4.00-3.40 (m,9H, 4CH2-
imidazole + 1H, CH-Ph)
3080 (CH-arom.), 1640 (C=N)
15
3050 (CH-arom.), 1640 (C=N).
9.10 (s,1H,CH), 7.70-7.20 (m,5H,arom.), 4.00-3.40
(m,10H,4CH2-imidazole+ OCH2), 1.25-1.00 (t,3H,CH3).
16
3200 (NH), 2220,2210,2197 (4CN), 9.00 (s,1H,NH), 7.70-7.20 (m,5H,arom.), 4.00-3.40
1620 (C=N). (m,8H,4CH2-imidazole).
3200 (NH), 1690,1670 (C=O), 1640 8.90 (s,1H,NH), 7.70-7.00 (m,5H,arom.), 4.00-3.40
17a
17b
18
(C=N).
(m,,8H,4CH2-imidazole), 2.70-2.60 (ss, 12H,2COCH3).
8.70 (s,1H,NH), 8.40 (s,1H,NH), 7.70-7.20 (m, 5H,arom.),
4.00-3.50 (m,8H,4CH2-imidazole).
3050 (CH-arom.), 1640 (C=N).
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Sample Availability: Available from the author.
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