A one-pot, efficient synthesis of polyfunctionalized pyrido[2,3-d] pyrimidines and uncyclized adducts by aldehydes, 1,3-dicarbonyl compounds, and 6-aminouracils

Article abstract of DOI:10.1002/jhet.1704

A one-pot, efficient protocol for the synthesis of polyfunctionalized pyrido[2,3-d]pyrimidines and uncyclized adducts by 6-aminouracils in poly(ethylene glycol) 200/H₂O or AcOH was described. An interesting family of pyrido[2,3-d]pyrimidines and uncyclized adducts bearing fused pharmacological active units are prepared. The reaction is free of toxic solvents and catalysts, has simple workup procedure, and has high atom economy, making it more environmentally friendly and suitable for large-scale operations.

Full text of DOI:10.1002/jhet.1704

November 2014
A One-pot, Efficient Synthesis of Polyfunctionalized Pyrido[2,3-d]
pyrimidines and Uncyclized Adducts by Aldehydes, 1,3-Dicarbonyl
Compounds, and 6-Aminouracils
1595
*
Guo-ping Lu and Chun Cai
College of Chemical Engineering, Nanjing University of Science and Technology, 200 Xiaoling Wei, Nanjing 210094, China
*
E-mail: c.cai@mail.njust.edu.cn
Received December 23, 2011
DOI 10.1002/jhet.1704
Published online 16 May 2014 in Wiley Online Library (wileyonlinelibrary.com).
A one-pot, efficient protocol for the synthesis of polyfunctionalized pyrido[2,3-d]pyrimidines and
uncyclized adducts by 6-aminouracils in poly(ethylene glycol) 200/H2O or AcOH was described. An
interesting family of pyrido[2,3-d]pyrimidines and uncyclized adducts bearing fused pharmacological active
units are prepared. The reaction is free of toxic solvents and catalysts, has simple workup procedure, and has
high atom economy, making it more environmentally friendly and suitable for large-scale operations.
J. Heterocyclic Chem., 51, 1595 (2014).
INTRODUCTION
discovered [18–22]. 6-Aminouracils as an important class
of uracil derivatives have been also applied to the synthesis
of pyrido[2,3-d] pyrimidine compounds, which display a
wide range of pharmacological activities [23–28].
Because of growing environmental concerns, designing
highly efficient chemical synthetic methods that provide
maximum structural complexity and diversity with a
minimum number of synthetic steps and maximum atom
utilization to assemble compounds with interesting
structures and properties have become a highly topical
area in Green Chemistry [1–3]. One of the powerful tools
to achieve the goal is the development of multicomponent
reactions, by which several different starting materials can
be combined in one reaction to give a highly complex
product [4–7].
Today, in the chemical industry, especially in the fine-
chemical and pharmaceutical production, large amounts
of solvents are used per mass of final products. Therefore,
solvents are a major part of the environmental performance
of a chemical process, and the adoption of “green” solvents
will be effective to minimize the environmental impact
resulting from the use of solvents in chemical production
[8,9], such as ionic liquid [10,11], poly(ethylene glycol)
(PEG) [12,13], and water [14,15]. Uracil found in RNA
is a common and naturally occurring pyrimidine derivative
[16,17]. Many useful anticancer and antiviral drugs
containing uracil structures have been synthesized and
Along this line, we envisage to explore the multi-
component reactions of 6-aminouracils in “green”
solvents. Herein, we describe an efficient protocol for the
formation of polyfunctionalized pyrido[2,3-d]pyrimidines
and uncyclized adducts in PEG 200/H2O or AcOH by
6-aminouracils. A series of pyrido[2,3-d]pyrimidines and
uncyclized adducts containing pharmacological active
structures including coumarone, spiroindolone, benzo-
phenazine, and naphthoquinone are synthesized. All the
structures are widely present in a number of biologically
active and medicinal agents [29–33], such as antitumor
agents (A and E), anticoagulants (B), inhibitors of
microtubule assembly (C), and dual topo I/II inhibitors
(D) (Figure 1).
RESULTS AND DISCUSSION
As a part of interests in using “green” solvents as the
reaction medium, we have reported the synthesis of
dihydrothiophene ureidoformamides in PEG/H2O [34].
© 2014 HeteroCorporation

1596
G.-P. Lu and C. Cai
Vol 51
NH2
N
OMe
OMe
CF3
N
OH
O
H2N
N
O
O
BW301U (A)
Flocoumafen (B)
N
N
O
O
MeO
O
O
N
N
OH
O
HN
O
O
O
N
N
H
MeO
Spirotryprostatin A (C)
Rhinacanthin-M (E)
XR11576 (D)
Figure 1. Some representative biologically active and medicinal agents.
Thus, we performed a testing reaction of 1a, 2a, and 3a in
PEG 200/H2O under catalyst-free conditions at 80ꢀC, and
an uncyclized adduct 4a was obtained as the final product.
Several solvents were screened to further explore the
solvent effects on the reaction (Table 1). It was found that
both the polar protic and aprotic solvents had promotive
effects on the reaction and provided low to moderate yields
(Table 1, entries 3–11), whereas the nonpolar solvent could
not afford the desired product (Table 1, entry 2). It should
be noted that the similar yields can be obtained using PEG
with different molecular weights (Table 1, entries 9–11).
Among these solvents, PEG 200/H2O proved to be the best
choice (Table 1, entry 1). The reasons for this could be
explained as follows: (1) The use of PEG 200 increases
the solubility of reactants, which leads to larger interfacial
area and lower mass transfer resistance [35]. (2) The promo-
tive effects of water on the reaction could be attributed to its
hydrophobic, polarity, and hydrobonding effects [36,37].
A brief study was also made to recycle the reaction
medium (PEG 200/H2O). After the reaction completed,
the reaction medium was seperated by filtration and reused
in the next run directly. The results indicated that a slightly
lower yield (74%) was obtained in the first run, because
some product dissolved in the PEG 200/H2O (Table 1,
Table 1
The solvent effects on the reaction.a
Entry
Solvent (4 mL)
Temperature (ꢀC)
Yield (%)b
1
2
3
4
5
6
7
PEG 200/H2O(v/v = 1:1)
Hexane
80
Reflux
Reflux
80
Reflux
Reflux
80
84
Trace
34
38
46
42
26
THF
1,4-Dioxane
CH3CN
CH2Cl2
H2O
8
9
EtOH
PEG 200
Reflux
80
55
78
10
11
12c
PEG 400
PEG 600
PEG 200/H2O(v/v = 1:1)
80
80
80
77
79
74, 82, 81, 83d
aReaction conditions: 1a 1 mmol; 2a 1 mmol; 3a 1 mmol; solvent 4 mL, 4 h.
bIsolated yields.
c2.5-mmol scale.
dThe solvent is reused for four times.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

November 2014 A One-pot, Efficient Synthesis of Polyfunctionalized Pyrido[2,3-d]pyrimidines and
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Uncyclized Adducts by Aldehydes, 1,3-Dicarbonyl Compounds, and 6-Aminouracils
entry 12). The medium would be saturated since the second
run, so the yields were better than the first run.
the reactions of 1j–k, 2a, and 3d could proceed smoothly
under identical conditions, and two spiroindeno[1,2-b]
pyrido[2,3-d]pyrimidine compounds 5w–x were obtained.
However, other 1,3-dicarbonyl compounds 3a–c failed to
react with 1j–k and 2a to afford the desired products.
Domino reactions, defined as processes of two or more
bond-forming reactions under identical conditions, allow
the efficient synthesis of complex molecules from simple
substrates in an ecologically and economically favorable
way [39,40]. Thus, we also focused on the domino
reactions of 6-aminouracils to further broaden the scope
of the method. Initially, 6 reacted with 3d in PEG 200/
H2O for 5 min at 80ꢀC, and then the mixture of 1a and 2a
was added and stirred for 6 h at the same temperature.
Unfortunately, no desired cyclized or uncyclized product
was obtained, because 6 could not react with 3d to afford
the intermediate 7 in PEG 200/H2O in the absence of
catalysts. The reaction in PEG 200/H2O using catalytic
AcOH could provide 7; however, it failed to react with 1a
and 2a to afford the desired product.
To solve the problem, AcOH was selected as the reaction
medium to ensure that the reaction of 6 and 3d occurred to
yield 7, which could also react with 1a and 2a to form an
uncyclized product 8a. Various benzaldehydes 1a–e could
be applied to the process successfully to produce uncyclized
products 8a–e (Table 3, entries 1–5). However, 2b in place
of 2a led to a mixture of cyclized and uncyclized products
(Table 3, entry 6).
In conclusion, we have demonstrated a simple and
efficient route for the formation of polyfunctionalized
pyrido[2,3-d]pyrimidines and uncyclized adducts by
6-aminouracils. The simplicity of the method, free of toxic
Encouraged by the remarkable results, a series of aldehydes
(1a–c, 1f–i), 6-aminouracils (2a–b), and 1,3-dicarbonyl
compounds (3a–d) (Figure 2) were used to ascertain the
scope and generality of the protocol (Table 2). It was notable
that the characteristics of 1, 2, and 3 had an important
influence on the final products. All final products were
uncyclized adducts 4a–e when 3a was employed, even in
the presence of p-toluenesulfonic acid (Table 2, entries 1–6).
Nevertheless, both cyclized and uncyclized products
could yield using 3b–d as 1,3-dicarbonyl compounds.
Probably, the electronic effects of aldehyde 1 were the
main reason for these outcomes. Usually, electron-rich
aldehydes were more likely to provide the pyrido[2,3-d]
pyrimidine compounds (Table 2, entries 10, 11, 16,
21, 25, and 26). It was also found that a mixture of
cyclized and uncyclized products was produced in
some cases (Table 2, entries 14, 9 vs 14), and the
further cyclization could happen to afford all cyclized
product 5 when p-toluenesulfonic acid was added (Table 2,
entries 8, 15, 18, and 20).
It could be concluded that electron-rich aldehydes may
enhance the nucleophilicity of 4’s amino group, making it
easier to form cyclized products 5; meanwhile, the products
cyclized or not may also depend on the electrophilicity of
3’s carbonyl carbon. In addition, 2b compared with 2a is
preferred to result in cyclized products (Table 2, entries
9 vs 14), owing to its weak acidity [38].
Preliminary efforts were also made to use isatins in
place of aldehydes in the process to synthesize the
spiroindolone derivatives (Scheme 1). To our delight,
Figure 2. The chemical structures of 1a–k, 2a–b, and 3a–d.
Journal of Heterocyclic Chemistry
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G.-P. Lu and C. Cai
Vol 51
Table 2
The reaction of aldehydes, 6-aminouracils, and 1,3-dicarbonyl compounds.a
Entry
1
2
3
Time (h)
Yield of 4 (%)b
4a
4a
4b
4c
4d
4e
4f
Yield of 5 (%)b
1
1a
1a
1b
1c
1h
1i
1a
1a
1b
1c
1f
1h
1a
1b
1b
1c
1a
1a
1b
1b
1f
2a
2a
2a
2a
2a
2a
2a
2a
2a
2a
2a
2a
2b
2b
2b
2b
2a
2a
2a
2a
2a
2a
2a
2a
2a
2a
2a
3a
3a
3a
3a
3a
3a
3b
3b
3b
3b
3b
3b
3b
3b
3b
3b
3c
3c
3c
3c
3c
3d
3d
3d
3d
3d
3d
4
4
4
6
2
4
4
4
4
6
4
2
4
4
4
6
6
6
6
6
6
4
4
6
4
4
2
84
82
93
83
79
73
83
0
5a
5a
5b
5c
5d
5e
5f
0
0
0
0
0
2c
3
4
5
6
0
0
7
8c
9
4f
5f
76
0
62
79
0
4g
4h
4i
78
0
0
5g
5h
5i
10
11
12
13
14
15c
16
17
18c
19
20c
21
22
23
24
25
26
27
4j
4k
4l
80
0
66
0
5j
5k
5l
5l
74
17
80
83
49
71
22
74
75
0
0
0
79
76
0
4l
4m
4n
4n
4o
4o
4p
4q
4r
4s
4t
0
19
0
45
0
0
82
91
78
0
5m
5n
5n
5o
5o
5p
5q
5r
5s
5t
1a
1b
1c
1f
1g
1h
4u
4v
0
77
5u
5v
aReaction conditions: 1 1 mmol; 2 1 mmol; 3 1 mmol; PEG 200/H2O (v/v = 1:1) 4 mL, 80ꢀC.
bIsolated yields, and the ratio of 4/5 is determined by 1H NMR.
c20 mol% p-toluenesulfonic acid is added.
Billerica, Massachusetts, USA) operating at 500 and 125 MHz in
DMSO-d6 or CDCl3, respectively, and chemical shifts were reported
in ppm. Elemental analyses were performed on a Yanagimoto
solvents and catalysts, and the recyclability of reaction
medium will make this synthetic method more environ-
mentally friendly and useful on an industrial scale. In
addition, the protocol also provides other advantages, such
as mild reaction conditions, high atom economy, and broad
substrate scope.
MT3CHN recorder (Yanagimoto, Saitama, Japan).
General procedure for the preparation of polyfunctionalized
pyrido[2,3-d]pyrimidines and uncyclized adducts in PEG
200/H2O.
1 (1 mmol), 2 (1 mmol), and 3 (1 mmol) were
weighed in a round bottom flask, and PEG 200/H2O (4 mL,
v/v = 1:1) was added at room temperature. The mixture was
allowed to stir at 80ꢀC for several hours and cooled to room
temperature. Water (10 mL) was added, and the precipitate
was collected by filtration and washed with water. The crude
product was recrystallized or washed with ethanol to give the
EXPERIMENTAL
All chemical reagents were obtained from commercial suppliers
and used without further purification. Analytical thin-layer chroma-
tography were performed on glass plates precoated with silica gel
impregnated with a fluorescent indicator (254nm), and the plates
were visualized by exposure to ultraviolet light. All melting points
were uncorrected. Mass spectra were taken on a Finnigan TSQ
Quantum-MS instrument (Finnigan, Palo Alto, California, USA)
in the electrospray ionization (ESI) mode. 1H and 13C NMR spectra
were recorded on an AVANCE 500 Bruker spectrometer (Bruker,
pure product.
General procedure for the preparation of polyfunctionalized
pyrido[2,3-d]pyrimidines and uncyclized adducts in
AcOH.
3d (1 mmol) and 6 (1 mmol) were weighed in a
round bottom flask, and AcOH (4 mL) was added at room
temperature. The mixture was allowed to stir at 80ꢀC for
5 min. Then, 1 (1 mmol) and 2 (1 mmol) were added. The
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

November 2014 A One-pot, Efficient Synthesis of Polyfunctionalized Pyrido[2,3-d]pyrimidines and
1599
Uncyclized Adducts by Aldehydes, 1,3-Dicarbonyl Compounds, and 6-Aminouracils
Scheme 1
reaction was stirred at the same temperature for additional 6 h and
cooled to room temperature. Water (10 mL) was added, and the
precipitate was collected by filtration and washed with water.
The crude product was recrystallized or washed with ethanol to
give the pure product.
116.61, 117.38, 124.21, 124.80, 128.41, 128.94, 130.79, 132.97,
138.01, 150.50, 152.44, 155.65, 164.28, 164.54, 166.15. MS (ESI)
m/z: 438 (Mꢁ H)ꢁ. Anal. Calcd for C22H18ClN3O5: C, 60.07%; H,
4.12%; N, 9.55%. Found: C, 60.19%; H, 4.37%; N, 9.25%.
6-Amino-5-((4-hydroxy-2-oxo-2H-chromen-3-yl)(4-methoxyphenyl)
methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 4c. Light yellow
solid, mp: 178–180ꢀC. 1H NMR (500 MHz, DMSO-d6) d =3.16–3.18
(t, 3H), 3.39–4.10 (t, 3H), 3.71–3.73 (t, 3H), 5.59 (d, 1H, J=6.5Hz),
6.79–6.83 (m, 2H), 7.05–7.08 (t, 2H), 7.34–7.47 (m, 4H), 7.66 (d, 1H,
J= 7.5 Hz), 7.84–7.87 (t, 1H), 14.00 (s, 1H). 13C NMR (125 MHz,
DMSO-d6) d = 28.67, 31.01, 35.81, 55.41, 87.41, 105.42, 113.94,
116.60, 117.43, 124.16, 124.77, 127.92, 130.33, 132.85, 150.52,
152.40, 155.53, 157.82, 164.23, 164.52, 166.28. MS (ESI) m/z: 434
(M ꢁ H)ꢁ. Anal. Calcd for C23H21N3O6: C, 63.44%; H, 4.86%; N,
Procedure for recycling the reaction medium.
After
cooling to room temperature, the reaction medium (PEG 200/H2O)
was separated by filtration and reused in the next run directly.
Characterization data for unknown compounds.
6-Amino-5-((4-hydroxy-2-oxo-2H-chromen-3-yl)(phenyl)methyl)-
1,3-dimethylpyrimidine-2,4(1H,3H)-dione 4a. White solid, mp:
220–222ꢀC. 1H NMR (500 MHz, DMSO-d6) d =3.16 (s, 3H),
3.40 (s, 3H), 5.63 (s, 1H), 7.16–7.26 (m, 5H), 7.33–7.46 (m, 4H),
7.64–7.67 (t, 1H), 7.86 (d, 1H, J = 8.0 Hz), 14.02 (s, 1H). 13C
NMR (125 MHz, DMSO-d6) 28.69, 31.03, 36.52, 87.27, 105.10,
116.60, 117.40, 124.18, 124.78, 126.15, 126.83, 128.57, 132.89,
138.75, 150.52, 152.42, 155.62, 164.29, 164.56, 166.29. MS (ESI)
m/z: 404 (Mꢁ H)ꢁ. Anal. Calcd for C22H19N3O5: C, 65.18%; H,
9.65%. Found: C, 63.48%; H, 4.59%; N, 9.58%.
6-Amino-5-(1-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-methylpropyl)-
1,3-dimethylpyrimidine-2,4(1H,3H)-dione 4d. White solid, mp: 222–
1
224ꢀC. H NMR (500 MHz, CDCl3) d = 0.93 (d, 6H, J = 2.5Hz),
3.22–3.29 (m, 1H), 3.41 (s, 3H), 3.57 (s, 3H), 3.70 (d, 1H,
J = 11.0 Hz), 6.47 (s, 2H), 7.28–7.33 (m, 2H), 7.52–7.56 (m, 1H),
7.99–8.00 (m, 1H), 13.88 (s, 1H). 13C NMR (125 MHz, CDCl3)
d = 21.82, 21.85, 26.23, 28.59, 29.87, 41.65, 89.28, 105.94,
116.06, 117.54, 124.21, 124.28, 131.85, 150.61, 152.40, 164.23,
165.04, 168.31. MS (ESI) m/z: 370 (Mꢁ H)ꢁ. Anal. Calcd for
4.72%; N, 10.37%. Found: C, 65.22%; H, 4.57%; N, 10.16%.
6-Amino-5-((4-chlorophenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)
methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 4b. White solid,
1
mp: 218–220ꢀC. H NMR (500 MHz, DMSO-d6) d = 3.16 (s, 3H),
3.39 (s, 3H), 5.62 (s, 1H), 7.19–7.86 (m, 9H), 13.99 (s, 1H). 13C
NMR (125 MHz, DMSO-d6) d = 28.70, 31.04, 36.18, 86.99, 104.98,
Table 3
The domino reactions of 1, 2, 3d, and 6 in AcOH.a
Entry
1
2
Yield of 8 (%)b
1
2
3
4
5
6
1a
1b
1c
1d
1e
1a
2a
2a
2a
2a
2a
2b
8a
8b
8c
8d
8e
8f
89
90
93
91
80
15 (78)c
aReaction conditions: After 3d (1 mmol) and 6 (1 mmol) were stirred for 5 min in AcOH (4 mL) at 80ꢀC, 1 (1 mmol) and 2 (1 mmol) were added and stirred
for 6 h at the same temperature.
bIsolated yields.
cThe yield of cyclized product 9f, determined by 1H NMR.
Journal of Heterocyclic Chemistry
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G.-P. Lu and C. Cai
Vol 51
C19H21N3O5: C, 61.45%; H, 5.70%; N, 11.31%. Found: C,
61.52%; H, 5.88%; N, 11.03%.
6-Amino-5-(cyclohexyl(4-hydroxy-2-oxo-2H-chromen-3-yl)
(m, 2H), 13.19 (s, 1H). 13C NMR (125 MHz, DMSO-d6)
d = 28.67, 30.93, 34.94, 85.89, 123.71, 126.16, 126.56, 128.36,
129.29, 130.72, 131.11, 132.23, 133.94, 134.80, 138.25, 150.66,
154.90, 159.06, 164.05, 181.52, 186.25. MS (ESI) m/z: 450
(M ꢁ H)ꢁ. Anal. Calcd for C23H18ClN3O5: C, 61.14%; H,
methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 4e. White
solid, mp: 214–216ꢀC. 1H NMR (500 MHz, CDCl3) d =0.82–0.92
(m, 2H), 1.12–1.17 (m, 1H), 1.23–1.33 (m, 2H), 1.62–1.71 (m, 5H),
2.86–2.92 (m, 1H), 3.40 (s, 3H), 3.51–3.53 (d, 3H), 3.83 (d, 0.7H,
J = 11.0 Hz), 4.19 (d, 0.3H, J = 11.0 Hz), 6.33 (s, 1.40H), 6.70
(s, 0.60H), 7.30–7.33 (t, 2H), 7.52–7.55 (t, 1H),7.97–8.00 (t, 1H),
12.82 (s, 0.3H), 13.81 (s, 0.7H). 13C NMR (125 MHz, CDCl3)
d = 26.01, 26.38, 28.62, 29.76, 32.12, 34.92, 39.96, 88.79,
105.36, 116.08, 117.52, 124.13, 124.20, 131.79, 150.59, 152.16,
154.29, 164.10, 165.04, 168.26. MS (ESI) m/z: 410 (M ꢁ H)ꢁ.
Anal. Calcd for C22H25N3O5: C, 64.22%; H, 6.12%; N, 10.21%.
4.02%; N, 9.30%. Found: C, 61.19%; H, 4.24%; N, 9.51%.
6-Amino-5-((3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)
(4-methoxyphenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-
1
dione 4s. Orange solid, mp: 220–222ꢀC. H NMR (500 MHz,
DMSO-d6) d = 3.15 (s, 3H), 3.37 (s, 3H), 3.72 (s, 3H), 5.78 (s, 1H),
6.80 (d, 2H, J= 9.0 Hz), 7.11 (d, 2H, J= 8.0 Hz), 7.16 (s, 2H),
7.79–7.86 (m, 2H), 7.98–8.03 (m, 2H), 13.18 (s, 1H). 13C NMR
(125 MHz, DMSO-d6) d = 28.62, 30.89, 34.55, 55.43, 86.39,
113.94, 124.29, 126.15, 126.53, 128.26, 130.41, 131.06, 132.22,
133.93, 134.79, 150.65, 154.80, 157.82, 159.01, 164.08, 181.42,
186.42. MS (ESI) m/z: 446 (M ꢁ H)ꢁ. Anal. Calcd for
C24H21N3O6: C, 64.42%; H, 4.73%; N, 9.39%. Found: C, 64.31%;
Found: C, 64.07%; H, 6.41%; N, 9.99%.
6-Amino-5-((2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)
(phenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 4f.
1
White solid, mp: 224–226ꢀC. H NMR (500 MHz, DMSO-d6)
H, 4.46%; N, 9.25%.
d = 1.05 (s, 3H), 1.13 (s, 3H), 2.25–2.40 (m, 4H), 3.11 (s, 3H),
3.36 (s, 3H), 5.48 (s, 1H), 7.09–7.13 (m, 3H), 7.22–7.25 (t, 2H),
7.29 (s, 2H), 12.82 (s, 1H). 13C NMR (125MHz, DMSO-d6)
d = 27.52, 28.47, 29.35, 30.80, 31.60, 33.46, 44.02, 49.97, 88.29,
114.19, 125.69, 126.79, 128.41, 140.25, 150.64. 155.10, 164.13,
176.52, 199.83. MS (ESI) m/z: 382 (Mꢁ H)ꢁ. Anal. Calcd for
C21H25N3O4: C, 65.78%; H, 6.57%; N, 10.96%. Found: C,
6-Amino-5-(1-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-
2-yl)-2-methylpropyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-
dione 4v. Orange solid, mp: 208–210ꢀC. 1H NMR (500MHz,
DMSO-d6) d = 0.81–0.84 (t, 6H), 3.00–3.05 (m, 1H), 3.20 (s, 3H),
3.35 (s, 3H), 3.73 (d, 1H, J= 9.0 Hz), 7.25 (s, 2H), 7.77–7.84 (m, 2H),
7.94–8.01 (m, 2H), 14.09 (s, 1H). 13C NMR (125 MHz, DMSO-d6)
d = 21.66, 22.08, 25.64, 28.66, 30.97, 86.50, 125.10, 126.14,
126.49, 130.98, 131.80, 134.04, 134.73, 150.38, 155.25, 158.71,
164.75, 181.43, 187.29. MS (ESI) m/z: 382 (M ꢁ H)ꢁ. Anal. Calcd
for C20H21N3O5: C, 62.65%; H, 5.52%; N, 10.96%. Found: C,
65.61%; H, 6.53%; N, 11.06%.
6-Amino-5-((4-chlorophenyl)(2-hydroxy-4,4-dimethyl-6-
oxocyclohex-1-enyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-
dione 4g. White solid, mp: >260ꢀC. 1H NMR (500MHz, CDCl3)
d = 1.12 (s, 3H), 1.22 (s, 3H), 2.30–2.47 (m, 4H), 3.30 (s, 3H), 3.50
(s, 3H), 5.55 (s, 1H), 6.53 (s, 2H), 7.09 (d, 2H, J = 8.0 Hz), 7.23–
7.28 (d, 2H, J = 8.5 Hz), 12.70 (s, 1H). 13C NMR (125 MHz,
CDCl3) d = 27.40, 28.59, 29.67, 29.72, 31.45, 33.17, 44.38,
50.13, 89.72, 114.20, 127.92, 128.36, 131.53, 137.55, 150.68,
154.19, 164.42, 177.52, 200.79. MS (ESI) m/z: 416 (Mꢁ H)ꢁ.
Anal. Calcd for C21H24ClN3O4: C, 60.36%; H, 5.79%; N,
62.36%; H, 5.40%; N, 11.27%.
5-(4-Methoxyphenyl)-1,3,8,8-tetramethyl-7,8,9,10-tetrahydropyrimido
[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione 5h. White solid, mp: >260ꢀC
1
(lit.: >300ꢀC [1]). H NMR (500 MHz, DMSO-d6) d = 0.89 (s, 3H),
1.04 (s, 3H), 2.03 (d, 1H, J= 16.5 Hz), 2.21 (d, 1H, J= 16.0 Hz), 2.51–
2.61 (m, 2H), 3.09 (s, 3H), 3.44 (s, 3H), 3.66 (s, 3H), 4.81 (s, 1H),
6.73 (d, 2H, J= 8.0 Hz), 7.12 (d, 2H, J= 7.5 Hz), 8.97 (s, 1H). 13C
NMR (125 MHz, DMSO-d6) d = 26.94, 28.07, 29.56, 30.62, 32.55,
33.32, 50.55, 55.35, 90.85, 112.35, 113.51, 129.03, 139.14, 144.07,
149.68, 151.00, 157.88, 161.14, 195.01. MS (ESI) m/z: 394 (M ꢁ H)ꢁ.
Anal. Calcd for C22H25N3O4: C, 66.82%; H, 6.37%; N, 10.63%.
10.06%. Found: C, 60.64%; H, 5.55%; N, 9.98%.
6-Amino-5-(1-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)-
2-methylpropyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 4j.
White solid, mp: 216–218ꢀC. 1H NMR (500 MHz, CDCl3)
d = 0.83 (d, 3H, J= 6.0 Hz), 0.89 (d, 3H, J= 6.5 Hz), 1.07 (s, 3H),
1.09 (s, 3H), 2.20–2.29 (m, 2H), 2.36 (s, 2H), 3.02–3.07 (m, 1H),
3.36 (s, 3H), 3.46 (s, 3H), 3.56 (d, 1H, J = 11.0 Hz), 6.27 (s, 2H),
12.99 (s, 1H). 13C NMR (125 MHz, CDCl3) d = 21.99, 22.05,
26.06, 26.92, 28.43, 29.50, 29.96, 31.19, 38.56, 44.30, 50.11,
90.16, 116.13, 150.74, 153.70, 164.81, 176.11, 201.26. MS (ESI)
m/z: 348 (Mꢁ H)ꢁ. Anal. Calcd for C18H27N3O4: C, 61.87%; H,
Found: C, 66.65%; H, 6.28%; N, 10.79%.
1,3,8,8-Tetramethyl-5-(naphthalen-1-yl)-7,8,9,10-tetrahydropyrimido
[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione 5i. White solid, mp: >260ꢀC.
1H NMR (500 MHz, DMSO-d6) d = 0.84 (s, 3H), 1.04 (s, 3H),
1.92 (d, 1H, J = 16.0 Hz), 2.19 (d, 1H, J = 16.0 Hz), 2.57–2.67
(m, 2H), 3.00 (s, 3H), 3.50 (s, 3H), 5.67 (s, 1H), 7.35–7.81
(m, 6H), 8.80 (d, 1H, J = 8.5 Hz), 9.08 (s, 1H). 13C NMR
(125 MHz, DMSO-d6) d = 26.69, 28.01, 29.67, 30.73, 32.50,
50.46, 92.43, 113.82, 125.44, 125.61, 125.93, 126.34, 126.59,
126.89, 127.99, 131.31, 133.17, 144.10, 146.05, 149.50,
150.50, 161.32, 195.09. MS (ESI) m/z: 414 (M ꢁ H)ꢁ. Anal.
Calcd for C25H25N3O3: C, 72.27%; H, 6.06%; N, 10.11%.
7.79%; N, 12.03%. Found: C, 61.76%; H, 7.73%; N, 11.92%.
6-Amino-5-((3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)
(phenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 4q.
Orange solid, mp: 244–246ꢀC. 1H NMR (500 MHz, DMSO-d6)
d = 3.15 (s, 3H), 3.38 (s, 3H), 5.86 (s, 1H), 7.16–7.25 (m, 7H), 7.81–
7.86 (m, 2H), 7.99–8.03 (m, 2H), 13.23 (s, 1H). 13C NMR
(125 MHz, DMSO-d6) d = 28.64, 30.91, 35.25, 86.15, 123.97, 126.12,
126.42, 126.54, 127.17, 128.08, 128.54, 131.07, 132.21, 133.94,
134.80, 138.85, 150.65, 154.90, 159.07, 164.13, 181.55, 186.41. MS
(ESI) m/z: 416 (Mꢁ H)ꢁ. Anal. Calcd for C23H19N3O5: C, 66.18%;
Found: C, 71.96%; H, 6.18%; N, 10.42%.
8,8-Dimethyl-5-phenyl-7,8,9,10-tetrahydropyrimido[4,5-b]
quinoline-2,4,6(1H,3H,5H)-trione 5k. White solid, mp:
1
>260ꢀC. H NMR (500MHz, DMSO-d6) d = 0.89 (s, 3H), 1.02
(s, 3H), 2.02 (d, 1H, J = 16.0 Hz), 2.20 (d, 1H, J = 16.0 Hz),
2.41–2.50 (m, 2H), 4.75 (s, 1H), 7.06–7.10 (m, 1H), 7.17–7.20
(t, 4H), 8.77 (s, 1H), 10.74 (s, 1H). 13C NMR (125 MHz,
DMSO-d6) d = 26.91, 29.43, 32.60, 33.47, 39.98, 50.60, 90.11,
111.74, 126.28, 128.01, 128.18, 144.20, 146.93, 149.62, 150.29,
163.16, 194.78. MS (ESI) m/z: 336 (Mꢁ H)ꢁ. Anal. Calcd for
C19H19N3O3: C, 67.64%; H, 5.68%; N, 12.46%. Found: C,
67.94%; H, 6.03%; N, 12.65%.
H, 4.59%; N, 10.07%. Found: C, 66.11%; H, 4.73%; N, 9.95%.
6-Amino-5-((4-chlorophenyl)(3-hydroxy-1,4-dioxo-1,4-
dihydronaphthalen-2-yl)methyl)-1,3-dimethylpyrimidine-2,4
(1H,3H)-dione 4r. Yellow solid, mp: 226–228ꢀC. 1H NMR
(500 MHz, DMSO-d6) d = 3.15 (s, 3H), 3.37 (s, 3H), 5.84 (s, 1H),
7.21 (s, 2H), 7.25–7.29 (m, 4H), 7.80–7.86 (m, 2H), 7.99–8.03
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

November 2014 A One-pot, Efficient Synthesis of Polyfunctionalized Pyrido[2,3-d]pyrimidines and
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Uncyclized Adducts by Aldehydes, 1,3-Dicarbonyl Compounds, and 6-Aminouracils
5-(4-Methoxyphenyl)-8,8-dimethyl-7,8,9,10-tetrahydropyrimido
6.87–6.91 (t, 2H), 7.82–7.87 (m, 3H), 8.07 (d, 1H, J = 7.0 Hz),
8.66 (s, 1H), 10.35 (s, 1H). 13C NMR (125 MHz, DMSO-d6)
d = 21.05, 28.11, 30.33, 50.21, 90.33, 108.65, 118.66, 124.93,
126.48, 126.62, 128.90, 129.96, 130.01, 132.01, 134.21,
135.39, 135.89, 136.07, 139.25, 141.18, 150.55, 159.58,
179.31, 180.93, 182.14. MS (ESI) m/z: 453 (M ꢁ H)ꢁ. Anal.
Calcd for C25H18N4O5: C, 66.08%; H, 3.99%; N, 12.33%.
[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione 5m. White solid, mp:
1
>260ꢀC. H NMR (500 MHz, DMSO-d6) d = 0.89 (s, 3H), 1.02
(s, 3H), 2.01 (d, 1H, J = 16.0 Hz), 2.19 (d, 1H, J = 16.0 Hz),
2.39–2.49 (m, 2H), 3.67 (s, 3H), 4.69 (s, 1H), 6.74 (d, 2H,
J = 8.5 Hz), 7.09 (d, 2H, J = 8.0 Hz), 8.72 (s, 1H), 10.20 (s, 1H),
10.72 (s, 1H). 13C NMR (125MHz, DMSO-d6) d = 26.94, 29.44,
32.56, 32.58, 50.63, 55.35, 90.36, 111.96, 113.55, 128.92,
139.25, 144.01, 149.29, 150.30, 157.85, 163.17, 194.79. MS
(ESI) m/z: 366 (Mꢁ H)ꢁ. Anal. Calcd for C20H21N3O4: C,
65.38%; H, 5.76%; N, 11.44%. Found: C, 65.39%; H, 6.04%; N,
Found: C, 65.96%; H, 4.14%; N, 12.27%.
6-Amino-5-((5-hydroxybenzo[a]phenazin-6-yl)(phenyl)methyl)-
1,3-dimethylpyrimidine-2,4(1H,3H)-dione 8a. Carmine solid, mp:
>260ꢀC. 1H NMR (500 MHz, DMSO-d6) d = 3.20 (s, 3H), 3.39
(s, 3H), 6.92 (s, 1H), 7.14–7.25 (m, 5H), 7.91–8.01 (m, 4H),
8.22 (br, 3H), 8.37 (d, 2H, J = 8.5 Hz), 9.29 (d, 1H, J = 4.5 Hz),
13.34 (s, 1H). 13C NMR (125 MHz, DMSO-d6) d = 28.63,
30.92, 36.09, 87.46, 114.64, 124.14, 125.05, 125.84, 127.08,
127.89, 128.48, 129.21, 129.40, 129.61, 130.25, 130.52,
130.85, 131.16, 139.70, 140.05, 140.40, 141.03, 150.72,
155.91, 156.77, 164.55. MS (ESI) m/z: 488 (M ꢁ H)ꢁ. Anal.
Calcd for C29H23N5O3: C, 71.15%; H, 4.74%; N, 14.31%.
11.77%.
1,3-Dimethyl-5-(naphthalen-1-yl)-7,8,9,10-tetrahydropyrimido
[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione 5p. White solid, mp:
1
>260ꢀC. H NMR (500MHz, DMSO-d6) d = 1.74 (br, 1H), 1.92
(br, 1H), 2.09–2.24 (m, 2H), 2.61–2.84 (m, 2H), 3.00 (s, 3H),
3.51 (s, 3H), 5.69 (s, 1H), 7.32–7.80 (m, 6H), 8.83 (d, 1H,
J = 8.5 Hz), 9.16 (s, 1H). 13C NMR (125 MHz, DMSO-d6)
d = 21.14, 27.04, 28.02, 29.53, 30.79, 92.45, 115.13, 125.44,
125.61, 126.14, 126.31, 126.56, 126.87, 127.97, 131.29,
133.15, 144.06, 146.33, 150.95, 151.49, 161.31, 195.36. MS
(ESI) m/z: 386 (M ꢁ H)ꢁ. Anal. Calcd for C23H21N3O3: C,
71.30%; H, 5.46%; N, 10.85%. Found: C, 71.63%; H, 5.28%;
Found: C, 71.24%; H, 4.85%; N, 14.53%.
6-Amino-5-((4-chlorophenyl)(5-hydroxybenzo[a]phenazin-6-yl)
methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 8b. Carmine
1
solid, mp: 226–228ꢀC. H NMR (500 MHz, DMSO-d6) d =3.20
(s, 3H), 3.38 (s, 3H), 6.87 (s, 1H), 7.20–7.28 (m, 4H), 7.89–7.99
(m, 4H), 8.23 (br, 3H), 8.35 (d, 2H, J=8.0Hz), 9.25–9.27 (t, 1H),
13.32 (s, 1H). 13C NMR (125 MHz, DMSO-d6) d = 28.65, 30.92,
35.78, 87.18, 114.45, 124.14, 125.03, 127.88, 128.33, 129.16,
129.25, 129.43, 129.60, 130.18, 130.44, 130.54, 130.84, 131.17,
139.25, 139.72, 140.38, 140.95, 144.87, 150.68, 155.95, 156.70,
164.48. MS (ESI) m/z: 522 (Mꢁ H)ꢁ. Anal. Calcd for
C29H22ClN5O3: C, 66.48%; H, 4.23%; N, 13.37%. Found: C,
N, 10.72%.
9,11-Dimethyl-7-(naphthalen-1-yl)benzo[h]pyrimido[4,5-b]
quinoline-5,6,8,10(7H,9H,11H,12H)-tetraone 5t. Red solid,
1
mp: 246–248ꢀC. H NMR (500 MHz, CDCl3) d = 3.24 (s, 3H),
3.71 (s, 3H), 6.24 (s, 1H), 7.28–7.39 (m, 3H), 7.52–7.55 (t, 1H),
7.63–7.81 (m, 5H), 7.93–7.95 (t, 1H), 8.11–8.12 (m, 1H), 9.00
(d, 1H, J = 8.5 Hz). 13C NMR (125 MHz, CDCl3) d = 28.30,
29.03, 31.07, 92.31, 122.66, 124.87, 125.19, 126.04, 126.30,
126.60, 126.93, 126.98, 128.26, 128.28, 129.92, 131.08, 132.41,
133.20, 133.39, 135.22, 135.87, 142.09, 143.34, 150.82, 161.25,
179.70, 181.87. MS (ESI) m/z: 448 (Mꢁ H)ꢁ. Anal. Calcd for
C27H19N3O4: C, 72.15%; H, 4.26%; N, 9.35%. Found: C,
66.49%; H, 4.32%; N, 13.59%.
6-Amino-5-((5-hydroxybenzo[a]phenazin-6-yl)(4-methoxyphenyl)
methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 8c. Carmine
solid, mp:>260ꢀC. 1H NMR (500 MHz, DMSO-d6) d = 3.20
(s, 3H), 3.38 (s, 3H), 3.70 (s, 3H), 6.79 (d, 2H, J = 8.5 Hz),
6.85 (s, 1H), 7.08 (d, 2H, J = 8.0 Hz), 7.91–8.01 (m, 4H),
8.21–8.25 (t, 3H), 8.37 (d, 2H, J = 8.0 Hz), 9.28–9.29 (t, 1H),
13.34 (s, 1H). 13C NMR (125 MHz, DMSO-d6) d = 28.61,
30.90, 35.32, 55.42, 113.89, 124.11, 125.04, 127.90, 128.10,
129.18, 129.39, 129.61, 130.26, 130.48, 130.85, 131.17,
139.67, 140.36, 145.29, 150.72, 157.64, 164.47. MS (ESI)
m/z: 518 (M ꢁ H)ꢁ. Anal. Calcd for C30H25N5O4: C, 69.35%;
H, 4.85%; N, 13.48%. Found: C, 69.46%; H, 4.97%; N,
71.89%; H, 4.36%; N, 9.59%.
9,11-Dimethyl-7-styrylbenzo[h]pyrimido[4,5-b]quinoline-5,6,8,10
1
(7H,9H,11H,12H)-tetraone 5u. Yellow solid, mp: 224–226ꢀC. H
NMR (500 MHz, DMSO-d6) d = 1.81 (d, 1H, J = 12.5Hz), 3.12
(s, 3H), 3.28 (s, 3H), 4.17 (d, 1H, J = 3.5 Hz), 4.60–4.64 (m, 1H),
7.19–7.32 (m, 5H), 7.79–8.02 (m, 4H), 11.39 (s, 1H). 13C NMR
(125MHz, DMSO-d6) d = 27.78, 29.69, 31.77, 35.76, 82.97,
121.21, 126.15, 126.35, 126.41, 127.88, 128.03, 128.55, 130.16,
132.59, 133.72, 135.37, 146.11, 150.30, 151.61, 156.90, 160.84,
181.60, 183.62. MS (ESI) m/z: 424 (Mꢁ H)ꢁ. Anal. Calcd for
C25H19N3O4: C, 70.58%; H, 4.50%; N, 9.88%. Found: C,
13.66%.
6-Amino-5-((5-hydroxybenzo[a]phenazin-6-yl)(4-hydroxyphenyl)
methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 8d. Carmine
solid, mp: 210–212ꢀC. 1H NMR (500 MHz, DMSO-d6)
d = 3.20 (s, 3H), 3.38 (s, 3H), 6.61 (d, 2H, J= 8.0 Hz), 6.81 (s, 1H),
6.95 (d, 2H, J= 8.0 Hz), 7.90–7.99 (m, 5H), 8.18–8.25 (m, 3H),
8.36 (d, 1H, J= 8.0 Hz), 9.09 (s, 1H), 9.29 (m, 1H), 13.34 (s, 1H).
13C NMR (125 MHz, DMSO-d6) d = 28.60, 30.87, 35.28, 87.81,
115.00, 124.08, 125.01, 125.25, 127.87, 127.98, 129.10, 129.32,
129.59, 129.71, 129.79, 130.28, 130.44, 130.80, 131.12, 139.62,
140.34, 141.00, 145.09, 150.72, 155.55, 155.77, 156.74, 164.44.
MS (ESI) m/z: 504 (Mꢁ H)ꢁ. Anal. Calcd for C29H23N5O4: C,
68.90%; H, 4.59%; N, 13.85%. Found: C, 69.25%; H, 4.78%; N,
70.24%; H, 4.35%; N, 10.21%.
9,11-Dimethyl-5H-spiro[benzo[h]pyrimido[4,5-b]quinoline-
7,30-indoline]-20,5,6,8,10(9H,11H,12H)-pentaone 5w. Brown
solid, mp: >260ꢀC. 1H NMR (500 MHz, DMSO-d6) d = 3.03
(s, 3H), 3.62 (s, 3H), 6.75–6.79 (t, 2H), 7.04–7.12 (m, 2H),
7.82–7.86 (m, 3H), 8.07 (d, 1H, J = 6.5 Hz), 8.70 (s, 1H),
10.46 (s, 1H). 13C NMR (125 MHz, DMSO-d6) d = 28.11,
30.37, 50.15, 90.27, 108.92, 118.92, 118.58, 121.31, 124.25,
126.50, 126.60, 128.66, 129.94, 131.99, 134.23, 135.90,
135.96, 143.58, 150.54, 159.61, 178.71, 179.36, 180.96. MS
(ESI) m/z: 439 (M ꢁ H)ꢁ. Anal. Calcd for C24H16N4O5: C,
65.45%; H, 3.66%; N, 12.72%. Found: C, 65.23%; H,
13.73%.
6-Amino-5-((4-nitrophenyl)(5-hydroxybenzo[a]phenazin-6-yl)
3.58%; N, 12.86%.
50,9,11-Trimethyl-5H-spiro[benzo[h]pyrimido[4,5-b]quinoline-
methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 8e. Carmine
solid, mp: 226–228ꢀC. 1H NMR (500 MHz, DMSO-d6) d =3.20
(s, 3H), 3.39 (s, 3H), 6.99 (s, 1H), 7.50 (d, 2H, J= 8.5 Hz), 7.90–
8.01 (m, 4H), 8.10 (d, 2H, J= 9.0 Hz), 8.26 (br, 3H), 8.37 (d, 2H,
7,30-indoline]-20,5,6,8,10(9H,11H,12H)-pentaone 5x. Brown
solid, mp: >260ꢀC. 1H NMR (500 MHz, DMSO-d6) d = 2.12
(s, 3H), 3.03 (s, 3H), 3.61 (s, 3H), 6.64 (d, 1H, J = 8.0 Hz),
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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G.-P. Lu and C. Cai
Vol 51
J=8.5Hz), 9.28–9.30 (m, 1H), 13.28 (s, 1H). 13C NMR (125 MHz,
DMSO-d6) = 28.70, 30.97, 36.73, 86.91, 114.24, 123.62, 124.23,
125.07, 127.93, 128.64, 129.41, 129.62, 130.16, 130.66, 130.90,
131.24, 131.44, 139.83, 140.44, 140.97, 146.09, 149.15, 150.68,
156.73, 164.62. MS (ESI) m/z: 533 (M ꢁ H)ꢁ. Anal. Calcd for
C29H22N6O5: C, 65.16%; H, 4.15%; N, 15.72%. Found: C,
[15] Firouzabadi, H.; Iranpoor, N.; Gholinejad, M. Adv Synth Catal
2010, 352, 119.
[16] Mashiyama, S. T.; Courtemanche, C.; Elson-Schwab, I. Anal
Biochem 2004, 330, 58.
[17] Kelly, R. E. A.; Kantorovich, L. N. J Phys Chem B 2006, 110, 2249.
[18] Zhi, C.; Long, Z. Y.; Gambino, J.; Xu, W. C. J Med Chem
2003, 46, 2731.
65.22%; H, 4.40%; N, 15.86%.
[19] Tucci, F. C.; Zhu, Y. F.; Struthers, R. S.; Guo, Z. J Med Chem
2005, 48, 1169.
16-Phenyl-5,16-dihydrobenzo[a]pyrimido[50,40:5,6]pyrido[2,3-
c]phenazine-1,3(2H,4H)-dione 9f. Brown solid, mp: >260ꢀC.
1H NMR (500 MHz, DMSO-d6) d = 5.31 (s, 1H), 7.06–7.10
(m, 2H), 7.18–7.23 (m, 3H), 7.86–7.95 (m, 4H), 8.16 (d, 1H,
J = 8.5 Hz), 8.29–8.36 (m, 2H), 9.28–9.30 (t, 1H), 10.32 (s, 1H),
10.52 (s, 1H), 11.54 (s, 1H). 13C NMR (125 MHz, DMSO-d6)
d = 32.89, 103.93, 123.38, 125.27, 125.35, 126.98, 128.10, 128.60,
128.99, 129.22, 129.73, 130.55, 130.69, 131.43, 139.73, 139.96,
143.01, 145.79, 150.22, 157.41. MS (ESI) m/z: 442 (M ꢁ H)ꢁ.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet