Metal-Free Organoselenium-Enabled Radical Relay Azidation-Carbocyclization

Article abstract of DOI:10.1002/adsc.202100208

An organoselenium-enabled radical relay Azidation-carbocyclization reaction for the preparation of azide-substituted quinoline-2,4-diones was developed. A series of previously unknown structurally diverse azide- substituted quinoline-2,4-diones were obtai

Full text of DOI:10.1002/adsc.202100208

RESEARCH ARTICLE
DOI: 10.1002/adsc.202100208
Metal-Free Organoselenium-Enabled Radical Relay Azidation-
Carbocyclization
+
a
+b
b
b,
b,
Xin Wang, Sa Guo, Yan Zhang, Zhiguo Zhang, * Guisheng Zhang, *
c
a,
Yong Ye, and Kai Sun *
a
College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005, Shandong,
E-mail: sunk468@nenu.edu.cn
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, People’s Republic of China
b
E-mail: zhangzg@htu.edu.cn; zgs@htu.cn
College of Chemistry, Zhengzhou University, Zhengzhou 450001, People’s Republic of China
c
+
These authors contributed equally to this work.
Manuscript received: February 15, 2021; Revised manuscript received: April 23, 2021;
Version of record online: ■■■, ■■■■
Supporting information for this article is available on the WWW under https://doi.org/10.1002/adsc.202100208
Abstract: An organoselenium-enabled radical relay Azidation-carbocyclization reaction for the preparation of
azide-substituted quinoline-2,4-diones was developed. A series of previously unknown structurally diverse
azide- substituted quinoline-2,4-diones were obtained under metal-free and room-temperature conditions. The
key features of this reaction are a broad substrate scope, amenability to gram-scale synthesis, and easy product
derivatization. Preliminary mechanistic studies support participation of an organoselenium species in a radical
relay pathway.
Keywords: metal free; radical relay; azidation; carbocyclization; organoselenium
Introduction
Organoselenium compounds are important in or-
[8,10d]
ganic synthesis, materials, and catalysis.
Among
The selective installation of azide groups in hetero- these, RSeN3 compounds are attractive potential
cyclic compounds is a priority research topic in organic candidates for use in organic chemistry. However, they
[1]
synthesis, particularly in pharmaceutical discovery.
were not isolated or characterized until 2004. Based on
Given the prevalence of azide motifs, the facile late- the successful structural characterization of ionic
stage diversification of azide groups to produce value- selenonium azides, i.e., [R Se]N , Klapötke’s group
3
3
added chemicals such as amines, imines, amides, first isolated the stable covalent selenium azide RSeN
3
[9]
aziridines, and triazoles is important but has not yet and reported its crystallographic data. As part of our
[2]
[10]
been fully explored. The development of sustainable ongoing interest in organoselenium chemistry,
we
and practical methods for forming CÀ N bonds in speculated that the interaction between (PhSe) and an
3
2
synthetic organic chemistry is therefore still organic azide, or the intermediate RSeN3 formed
[
3]
necessary.
Nitrogen-containing heterocycles are in situ, would undergo decomposition to form the
important, particularly structurally diverse quinoline- stable diselane and the corresponding azide radical,
,4-diones, which are widely found in numerous instead of producing dinitrogen. Based on these
natural products, pharmaceuticals, and assumptions, we developed a practical organosele-
agrochemicals. Although some methods have been nium-enabled radical relay Azidation-carbocyclization
[
4]
2
[5]
[6,5c]
reported for constructing quinoline-2,4-diones,
one- for the preparation of azide- substituted quinoline-2,4-
pot multi-bond-forming strategies, including multi- diones (Figure 1). Gram-scale synthesis, Huisgen [3+
component cascade reactions, are the best choices for 2] cyclization, and selective diversification via reduc-
attaining atom and step economies and therefore for tion show the practicability of the reaction and its
[7]
accessing these complex molecules.
potential use in industrial applications.
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transformation, and its use increased the yield of 2a to
90%. Other solvents, namely DMF, EtOAc, DCE, 1,4-
dioxane, and DCM, gave poorer results (Table 1,
entries 7–12). In addition, the reaction yield was
temperature sensitive and the yield of 2a decreased to
Figure 1. Organic selenium enabled azidation-carbocyclization. 74% at 60°C (Table 1, entry 13). Further condition
optimization showed that other diselenides, namely (4-
BrPhSe)2 and (4-MePhSe) , gave decreased yields
2
Results and Discussion
(Table 1, entries 14 and 15).
The scope with respect to N-(2-cyanophenyl)-N-
Initially, the reaction of N-(2-cyanophenyl)-N-meth- methylmethacrylamides 1 is wide. As shown in
ylmethacrylamide (1a) with azidotrimethylsilane Table 2, 1 with electron-withdrawing F, Cl, and Br
(
TMSN ) preactivated by (PhSe) and (diacetoxyiodo) substituents and electron-donating Me and MeO
3
2
benzene (PIDA) was performed in CH CN at room substituents at various positions on the phenyl ring
3
temperature. 3-(Azidomethyl)-1,3-dimethylquinoline- were successfully converted to the desired products
2
1
,4(1H,3H)-dione (2a) was obtained in 82% yield after 2b–2n. Note that the yield was affected by the
2 h (Table 1, entry 1). Condition screening showed electron density of the benzene ring. When 5-Cl- or 8-
that the yield of 2a decreased when the amount of Cl-substituted substrates were used, the yields de-
PhSe) or PIDA was decreased, and no 2a was formed creased to 43% and 16% of 2c and 2n, respectively.
(
2
in the absence of (PhSe) . This indicates that (PhSe) is Multi-substituted substrates reacted smoothly with
2
2
critical for the success of this reaction (Table 1, entries TMSN to provide 2o and 2p in 45% and 87% yields,
3
2
–6). The effects of the solvent were then investigated. respectively. The heterocyclic substrate pyridineacryla-
We found that DMSO, which is less volatile and less mide (1q), was also compatible with this reaction, and
toxic than CH CN, was the best solvent for this delivered 2q in 91% yield. The use of a benzyl
3
[a,b]
[a,b]
Table 1. Condition screenings.
Table 2. Substrate scope.
Entry
(PhSe)2
mol%)
PIDA
(equiv.)
Solvent
(mL)
Yield
(%)
[
b]
(
1
2
3
4
5
6
7
8
9
50
10
20
none
50
50
50
50
50
50
50
50
50
50
50
1.5
1.5
1.5
1.5
1.0
0.5
1.5
1.5
1.5
1.5
1.5
1.5
1.5
1.5
1.5
CH CN
82
21
39
0
68
49
41
43
59
90
33
49
3
CH CN
3
CH CN
3
CH CN
3
CH CN
3
CH CN
3
DMF
EtOAc
DCE
DMSO
1,4-dioxane
DCM
DMSO
DMSO
DMSO
1
0
1
1
12
13
14
15
[c]
[d]
[e]
74
72
36
[
a]
Reactions were performed with 1a (0.3 mmol), TMSN3
3.0 equiv.), (PhSe)2 (50 mol%), PIDA (1.5 equiv.), and
(
H O (2.0 equiv.) in a solvent (2 mL) at room temperature.
Yield of isolated product.
2
[
[
[
[
b]
[a]
Reaction conditions: 1 (0.3 mmol), TMSN3 (3.0 equiv.),
c]
d]
e]
Reaction performed at 60°C.
(PhSe) (0.5 equiv.), PIDA (1.5 equiv.), and H O (2.0 equiv.)
2
2
(
4-BrPhSe) (50 mol%) was added instead of (PhSe) .
in DMSO (2.0 mL) at room temperature for 12 h.
Yield of isolated product.
2
2
[b]
(4-MePhSe) (50 mol%) was added instead of (PhSe) .
2
2
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protecting group on the nitrogen atom was also
examined and found to be compatible with this trans-
formation; the desired 2r was obtained in 72% yield.
Substrate 1s, which has a phenyl group on the double
bond (R’’=Ph), gave 2s in 23% yield. This low yield
can be attributed to steric effects. The unprotected
substrate (R’=H) was also tested. Only trace amounts
of the quinoline-2,4-dione were detected; Azidation-
selenation occurred to give the vicinal azide and
seleno-substituted product 3 in 66% yield.
The reaction was scaled up to evaluate the synthetic
utility of this protocol. When the reaction of 1a was
performed on a 10 mmol scale (Scheme 1a), 2a was
obtained in 80% isolated yield. This enabled further
synthetic manipulations. Compound 2a was selectively
reduced to give 4 and 5 in excellent yields. These are
attractive as valuable cores for further derivatization
[11]
(
Scheme 1b and 1c). Given the prevalence of azide
motifs, further Huisgen [3+2] diversifications of the
azide group with 3-phenylpropiolic acid and ethister-
one were performed with 2a. The corresponding
triazoles 6 and 7 were obtained in 98% and 97%
yields, respectively (Scheme 1d and 1e).
After investigation of the substrate scope and
synthetic applications, control experiments were per-
formed to clarify the mechanism (see the Supporting
Scheme 2. Mechanism study.
Information for details). The addition of 2,6-di-tert- radical pathway was involved in these systems. A
butyl-4-methylphenol (BHT, 2.0 equiv.) and 2,2,6,6- control experiment showed that in the absence of H O
2
18
tetramethylpiperidine N-oxide (TEMPO, 2.0 equiv.) as the desired 2a was not detected (Scheme 2c). An O-
radical scavengers under the standard reaction con- labeling experiment was then performed. The desired
ditions significantly inhibited the reaction; the radical- product 2a’ was obtained in 37% yield after 3 h; the
trapping products 8 and 9 were detected by HRMS identity of 2a’ was confirmed by HRMS (Scheme 2d).
(
Scheme 2a and 2b). These results indicate that a Further control experiments showed that (PhSe) and
2
PIDA are both necessary for this Azidation-carbocycli-
zation reaction (Scheme 2e).
On the basis of the control experiment results and a
[12,13]
literature survey,
a plausible mechanism for the
formation of product 2 is proposed, as shown in
Scheme 3, First, oxygenolysis between (PhSe) and
2
PIDA generates PhSeOAc, which is similar to PhSeX
(
X=Cl, Br). Then the selenenyl azide PhSeN is
3
formed in situ as a suitable precursor for conversion to
the corresponding azide radical and diselane. The azide
Scheme 1. Application investigation.
Scheme 3. Proposed reaction mechanism.
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radical then attacks the activated alkenyl moiety in concentrated in vacuo. The residue was purified by flash
column chromatography with Ethyl acetate and Petroleum ether
as eluent to give 2.
substrate 1 to give radical intermediate A. Subsequent
rapid intramolecular 6-exo-dig cyclization of inter-
mediate A yields imine radical B, which undergoes
hydrogen abstraction to give imine C. Finally, imine C
3
-(Azidomethyl)-1,3-dimethylquinoline-2,4(1H,3H)-dione
(2a). Red liquid (66 mg, 90% yield). R (Petroleum ether: Ethyl
f
1
is hydrolyzed by H O to give 2.
acetate=3:1): 0.44. H NMR (400 MHz, CDCl ) δ 8.03 (d, J=
3
2
7
3
.8 Hz, 1H), 7.65 (t, J=7.8 Hz, 1H), 7.19 (t, J=7.4 Hz, 2H),
.97 (s, 2H), 3.49 (s, 3H), 1.38 (s, 3H). C NMR (150 MHz,
1
3
Conclusion
CDCl ) δ 195.47, 171.89, 143.19, 136.60, 128.31, 123.40,
3
1
19.77, 115.07, 57.11, 55.68, 29.97, 23.21. HRMS (ESI) calcd
In this work, an organoselenium-enabled radical relay
Azidation-carbocyclization was developed and used to
construct a series of structurally diverse azide- sub-
+
for C H N O [M+Na] : 267.0632, found: 267.0631.
12
12
4
2
3
-(Azidomethyl)-5-fluoro-1,3-dimethylquinoline-2,4(1H,3H)-
stituted quinoline-2,4-diones. With the unprotected dione (2b). Red liquid (55 mg, 70% yield). R (Petroleum ether:
f
1
substrate (R’=H) radical Azidation-selenation oc- Ethyl acetate=3:1): 0.29. H NMR (600 MHz, CDCl ) δ 7.60–
3
curred to give vicinal azide and seleno-substituted 7.56 (m, 1H), 6.99 (d, J=8.5 Hz, 1H), 6.91–6.88 (m, 1H), 3.97
(
1
1
d, J=11.5 Hz, 1H), 3.91 (d, J=11.5 Hz, 1H), 3.49 (s, 3H),
products. These reactions were conducted at room
temperature under metal-free conditions. Ease of
scaleup and potential product derivatization make this
strategy attractive for the preparation of other valuable
molecules. A possible mechanism, which involves
radical formation, was proposed on the basis of the
results of control experiments. A selenenyl azide
1
3
.40 (s, 3H). C NMR (150 MHz, CDCl ) δ 192.59, 171.27,
3
62.23 (d, J=267.1 Hz), 144.17 (d, J=3.0 Hz), 136.64 (d, J=
1
1.9 Hz), 111.61 (d, J=21.2 Hz), 110.85 (d, J=3.3 Hz), 109.72
1
9
(d, J=9.5 Hz), 57.99, 54.80, 30.79, 22.73.
F NMR
(
565 MHz, CDCl3) δ À 119.02. HRMS (ESI) calcd for
+
C H FN O [M+Na] : 285.0758, found: 285.0754.
12
11
4
2
3
-(Azidomethyl)-5-chloro-1,3-dimethylquinoline-2,4(1H,3H)-
(
PhSeN ) was proposed as a suitable precursor for
3
dione (2c). Red liquid (36 mg, 43% yield). R (Petroleum ether:
Ethyl acetate=3:1): 0.31. H NMR (600 MHz, CDCl ) δ 7.49
(
(
1
1
3
3
conversion to the corresponding azide radical. Further
research on the use of this protocol in the synthesis of
bioactive molecules and a detailed mechanistic inves-
tigation are currently in progress.
f
1
3
t, J=8.2 Hz, 1H), 7.24–7.23 (m, 1H), 7.13–1.11 (m, 1H), 3.94
d, J=11.7 Hz, 1H), 3.90 (d, J=11.7 Hz, 1H), 3.48 (s, 3H),
1
3
.39 (s, 3H). C NMR (150 MHz, CDCl ) δ 193.30, 170.64,
3
44.51, 135.62, 134.69, 126.76, 118.18, 113.87, 58.25, 54.19,
+
0.87, 21.77. HRMS (ESI) calcd for C H ClN O [M+Na] :
Experimental Section
12 11
4
2
01.0463, found: 301.0460.
General Remarks: All reagents were purchased from commer-
1
13
3
2
-(Azidomethyl)-5-bromo-1,3-dimethylquinoline-
cial sources and used without further purification. H NMR,
C
,4(1H,3H)-dione (2d). Red liquid (61 mg, 63% yield). Rf
NMR spectra were recorded on a Bruker Ascend™ 400 or a
Bruker Ascend™ 600 spectrometer in deuterated solvents
containing TMS as an internal reference standard. All high-
resolution mass spectra (HRMS) were measured on a mass
spectrometer by using electrospray ionization orthogonal accel-
eration time-of-flight (ESI-OA-TOF), and the purity of all
1
(Petroleum ether: Ethyl acetate=3:1): 0.34.
H NMR
(
1
600 MHz, CDCl ) δ 7.45–7.43 (m, 1H), 7.38 (t, J=8.1 Hz,
3
H), 7.16 (d, J=8.3 Hz, 1H), 3.92 (d, J=11.7 Hz, 1H), 3.88 (d,
1
3
J=11.7 Hz, 1H), 3.46 (s, 3H), 1.37 (s, 3H). C NMR
150 MHz, CDCl ) δ 193.60, 170.48, 144.59, 134.86, 130.33,
(
1
(
3
3
1
23.13, 119.37, 114.60, 58.03, 54.13, 30.81, 21.59. HRMS
samples used for HRMS (>95%) was confirmed by H NMR
+
13
ESI) calcd for C H BrN O [M+Na] : 344.9958, found:
and C NMR spectroscopic analysis. Melting points were
measured on a melting point apparatus equipped with a
thermometer and were uncorrected. All the reactions were
monitored by thin-layer chromatography (TLC) using GF254
silica gel-coated TLC plates. Purification by flash column
chromatography was performed over SiO2 (silica gel 200–
12 11 4 2
44.9955.
-(Azidomethyl)-6-fluoro-1,3-dimethylquinoline-2,4(1H,3H)-
3
dione (2e). Red liquid (52 mg, 66% yield). R (Petroleum ether:
Ethyl acetate=3:1): 0.34. H NMR (600 MHz, CDCl ) δ 7.72–
7
f
1
3
.70 (m, 1H), 7.39–7.36 (m, 1H), 7.19–7.17 (m, 1H), 4.00–3.95
300 mesh).
13
(m, 2H), 3.50 (s, 3H), 1.39 (s, 3H). C NMR (150 MHz,
CDCl ) δ 194.76, 171.47, 158.60 (d, J=245.6 Hz), 139.64,
3
1
7
23.56 (d, J=23.8 Hz), 120.94 (d, J=5.9 Hz), 116.93 (d, J=
The General Procedure for the Synthesis of 2
.5 Hz), 114.03 (d, J=23.2 Hz), 57.00, 55.81, 30.26, 23.14.
+
To a reaction tube were add acrylamides 1 (0.3 mmol), diphenyl
diselenide (50 mol%, 0.15 mmol, 46.8 mg), (diacetoxyiodo)
benzene (PIDA) (1.5 equiv., 0.45 mmol, 145 mg), TMSN3
HRMS (ESI) calcd for C H FN O [M+Na] : 285.0758,
found: 285.0755.
12
11
4
2
3
-(Azidomethyl)-6-chloro-1,3-dimethylquinoline-2,4(1H,3H)-
(
93%, 3.0 equiv., 0.9 mmol, 127 μL) and H O (2.0 equiv.) in
2
dione (2f). White soild (58.5 mg, 70% yield). R (Petroleum
f
DMSO (2 mL). Then the tube was stirred at room temperature
for 12 hours until complete consumption of starting material as
monitored by TLC analysis. After the completion of the
1
ether: Ethyl acetate=3:1) 0.46. mp 109–110°C. H NMR
(400 MHz, CDCl ): δ 7.96 (d, J=2.6 Hz, 1H), 7.59–7.56 (m,
3
1
3
1
H), 7.12 (d, J=8.9 Hz, 1H), 3.95 (s, 2H), 3.46 (s, 3H), 1.36 (s,
reaction, the mixture was quenched by H O (15 mL) and
2
13
H). C NMR (150 MHz, CDCl ) δ 194.51, 171.58, 141.71,
3
extracted with CH Cl (3×5 mL). Then the organic solvent was
2
2
36.17, 129.27, 127.74, 120.75, 116.71, 57.18, 55.74, 30.16,
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+
2
3.10. HRMS (ESI) calcd for C H ClN O [M+Na] :
3-(Azidomethyl)-7-methoxy-1,3-dimethylquinoline-
12
11
4
2
3
01.0463, found: 301.0460.
2,4(1H,3H)-dione (2m). Red liquid (67.5 mg, 82% yield). Rf
1
(Petroleum ether: Ethyl acetate=3:1): 0.33.
H NMR
3
2
-(Azidomethyl)-6-bromo-1,3-dimethylquinoline-
,4(1H,3H)-dione (2g). White soild (78.5 mg, 81% yield). R
(
600 MHz, CDCl ) δ 8.01 (d, J=8.7 Hz, 1H), 6.72–6.70 (m,
3
f
1
H), 6.62 (d, J=2.2 Hz, 1H), 3.97 (d, J=11.3 Hz, 1H), 3.93 (d,
1
(
Petroleum ether: Ethyl acetate=3:1): 0.43. mp 106–107°C. H
13
J=11.3 Hz, 1H), 3.91 (s, 3H), 3.46 (s, 3H), 1.37 (s, 3H).
NMR (150 MHz, CDCl ) δ 193.75, 172.49, 166.37, 145.20,
C
NMR (600 MHz, CDCl ) δ 8.12 (d, J=2.5 Hz, 1H), 7.74–7.72
(
3
3
m, 1H), 7.08 (d, J=8.8 Hz, 1H), 3.97 (s, 2H), 3.48 (s, 3H),
1
2
2
30.88, 113.67, 108.54, 101.11, 56.49, 56.05, 55.85, 29.91,
13
1
1
3
3
.39 (s, 3H). C NMR (150 MHz, CDCl ) δ 194.40, 171.58,
42.17, 139.03, 130.77, 121.05, 116.98, 116.49, 57.21, 55.74,
0.13, 23.11. HRMS (ESI) calcd for C H BrN O [M+Na] :
44.9958, found: 344.9958.
+
3
3.37. HRMS (ESI) calcd for C H N O [M+Na] :
13
14
4
3
67.0710, found: 297.0710.
+
12
11
4
2
3-(Azidomethyl)-8-chloro-1,3-dimethylquinoline-2,4(1H,3H)-
dione (2n). White soild (13 mg, 16% yield). R (Petroleum
f
3
-(Azidomethyl)-1,3,6-trimethylquinoline-2,4(1H,3H)-dione
1
ether: Ethyl acetate=3:1): 0.50. mp 80–81°C. H NMR
(2h). Red liquid (62 mg, 80% yield). R (Petroleum ether: Ethyl
f
(
600 MHz, CDCl ) δ 7.84–7.82 (m, 1H), 7.66–7.64 (m, 1H),
1
3
acetate=3:1): 0.41. H NMR (600 MHz, CDCl ) δ 7.83 (d, J=
3
7
.18 (t, J=7.8 Hz, 1H), 3.92 (d, J=11.8 Hz, 1H), 3.87 (d, J=
1.8 Hz, 1H), 7.47–7.45 (m, 1H), 7.08 (d, J=8.4 Hz, 1H), 3.97
13
11.8 Hz, 1H), 3.62 (s, 3H), 1.37 (s, 3H). C NMR (150 MHz,
1
3
(s, 2H), 3.48 (s, 3H), 2.36 (s, 3H), 1.38 (s, 3H). C NMR
CDCl ) δ 195.30, 171.94, 141.72, 138.60, 126.53, 125.27,
3
(150 MHz, CDCl ) δ 195.70, 171.77, 141.04, 137.38, 133.20,
3
1
24.78, 122.87, 57.76, 54.05, 37.48, 22.05. HRMS (ESI) calcd
+
1
28.23, 119.59, 115.04, 56.99, 55.75, 29.94, 23.22, 20.33.
for C H ClN O [M+Na] : 301.0463, found: 301.0462.
+
12 11
4
2
HRMS (ESI) calcd for C H N O [M+Na] : 281.1009,
13
14
4
2
found: 281.1004.
3-(Azidomethyl)-6,8-dichloro-1,3-dimethylquinoline-
,4(1H,3H)-dione (2o). Colourless liquid (42 mg, 45% yield).
2
3-(Azidomethyl)-7-fluoro-1,3-dimethylquinoline-2,4(1H,3H)-
1
Rf (Petroleum ether: Ethyl acetate=5:1): 0.48. H NMR
600 MHz, CDCl ) δ 7.79 (d, J=2.5 Hz, 1H), 7.64 (d, J=
dione (2i). Yellow liquid (60.5 mg, 77% yield). R (Petroleum
ether: Ethyl acetate=3:1): 0.51. H NMR (400 MHz, CDCl ) δ
f
(
1
3
3
2
1
1
1
.5 Hz, 1H), 3.92 (d, J=11.8 Hz, 1H), 3.86 (d, J=11.8 Hz,
8.12–8.06 (m, 1H), 6.93–6.87 (m, 2H), 4.01–3.95 (m, 2H), 3.48
13
H), 3.61 (s, 3H), 1.37 (s, 3H). C NMR (150 MHz, CDCl ) δ
1
3
3
(s, 3H), 1.40 (s, 3H). C NMR (100 MHz, CDCl ) δ 193.93,
3
94.30, 171.65, 140.43, 137.66, 130.43, 127.29, 126.27, 125.22,
1
1
2
72.09, 167.85 (d, J=256.8 Hz), 145.55 (d, J=11.7 Hz),
31.36 (d, J=11.4 Hz), 116.39 (d, J=2.3 Hz), 110.83 (d, J=
2.4 Hz), 102.74 (d, J=27.6 Hz), 56.98, 56.87, 30.14, 23.20.
23.68, 57.79, 54.04, 37.42, 22.02. HRMS (ESI) calcd for
+
C H Cl N O [M+Na] : 335.0073, found: 334.0070.
12
10
2
4
2
19
F NMR (565 MHz, CDCl ) δ À 98.04. HRMS (ESI) calcd for
3-(Azidomethyl)-6,7-dimethoxy-1,3-dimethylquinoline-
2,4(1H,3H)-dione (2p). Yellow solid (79.4 mg, 87% yield). Rf
3
+
C H FN O [M+Na] : 285.0758, found: 285.0753.
1
2
11
4
2
1
(
Petroleum ether: Ethyl acetate=3:1): 0.11. mp 138–139°C. H
3-(Azidomethyl)-7-chloro-1,3-dimethylquinoline-2,4(1H,3H)-
NMR (600 MHz, CDCl ) δ 7.46 (s, 1H), 6.61 (s, 1H), 4.00 (s,
H), 3.96 (d, J=11.3 Hz, 1H), 3.93 (d, J=11.3 Hz, 1H), 3.90
s, 3H), 3.49 (s, 3H), 1.37 (s, 3H). C NMR (150 MHz, CDCl3)
δ 192.95, 171.43, 155.11, 144.45, 138.53, 111.40, 107.88,
7.26, 55.37, 55.32, 55.27, 55.23, 28.96, 22.54. HRMS (ESI)
3
dione (2j). Yellow liquid (73.5 mg, 88% yield). R (Petroleum
ether: Ethyl acetate=3:1): 0.56. H NMR (600 MHz, CDCl ) δ
f
3
1
3
13
(
7
2
1
5
.97 (d, J=8.3 Hz, 1H), 7.19–7.16 (m, 2H), 3.97 (d, J=1.2 Hz,
H), 3.48 (s, 3H), 1.38 (s, 3H). C NMR (150 MHz, CDCl ) δ
94.38, 171.95, 144.16, 142.99, 129.73, 123.68, 118.13, 115.41,
7.14, 55.85, 30.11, 23.14. HRMS (ESI) calcd for
1
3
3
9
+
calcd for C H N O [M+Na] : 327.1064, found: 327.1069.
14
16
4
4
+
C H ClN O [M+Na] : 301.0463, found: 301.0460.
3-(Azidomethyl)-1,3-dimethyl-1,8-naphthyridine-
,4(1H,3H)-dione (2q). Yellow soild (67 mg, 91% yield). Rf
1
2
11
4
2
2
3
2
-(Azidomethyl)-7-bromo-1,3-dimethylquinoline-
,4(1H,3H)-dione (2k). Yellow liquid (77.5 mg, 80% yield). R
1
(
Petroleum ether: Ethyl acetate=3:1) 0.45. mp 56–57°C. H
f
NMR (600 MHz, CDCl ): δ 8.65–8.64 (m, 1H), 8.30–8.28 (m,
1
1
3
(Petroleum ether: Ethyl acetate=3:1): 0.55.
H NMR
H), 7.18–7.15 (m, 1H), 4.02 (d, J=11.4 Hz, 1H), 3.98 (d, J=
(600 MHz, CDCl ) δ 7.88 (d, J=8.3 Hz, 1H), 7.36 (d, J=
13
3
11.4 Hz, 1H), 3.63 (s, 3H), 1.43 (s, 3H). C NMR (150 MHz,
1
.6 Hz, 1H), 7.34–7.32 (m, 1H), 3.96 (s, 2H), 3.48 (s, 3H), 1.38
CDCl ) δ 195.11, 172.52, 154.71, 154.26, 136.76, 119.10,
13
3
(s, 3H). C NMR (150 MHz, CDCl ) δ 194.59, 171.90, 144.02,
3
1
15.02, 57.28, 56.01, 28.87, 23.07. HRMS (ESI) calcd for
1
5
34.08, 131.76, 129.63, 127.21, 126.65, 118.48, 118.35, 57.18,
+
C H N O [M+Na] : 268.0805, found: 268.0808.
1
1
11
5
4
5.83, 30.12, 23.12. HRMS (ESI) calcd for C H BrN O [M+
12
11
4
2
+
Na] : 344.9958, found: 344.9954.
3-(Azidomethyl)-1-benzyl-3-methylquinoline-2,4(1H,3H)-di-
one (2r). White soild (69 mg, 72% yield). R (Petroleum ether:
f
3
-(Azidomethyl)-1,3,7-trimethylquinoline-2,4(1H,3H)-dione
1
Ethyl acetate=3:1): 0.54. mp 155–156°C. H NMR (600 MHz,
(2l). Yellow liquid (65.8 mg, 85% yield). R (Petroleum ether:
f
CDCl ) δ 8.06–8.04 (m, 1H), 7.51–7.48 (m, 1H), 7.34 (t, J=
1
3
Ethyl acetate=3:1): 0.50. H NMR (600 MHz, CDCl ) δ 7.94–
7
3
7
.5 Hz, 2H), 7.26 (t, J=8.6 Hz, 3H), 7.15 (t, J=7.5 Hz, 1H),
.92 (m, 1H), 7.01 (d, J=7.9 Hz, 1H), 6.98 (s, 1H), 3.99–3.94
7
.06 (d, J=8.4 Hz, 1H), 5.39–5.27 (m, 2H), 4.07 (s, 2H), 1.50
1
3
(m, 2H), 3.49 (d, J=1.2 Hz, 3H), 2.46 (s, 3H), 1.38 (s, 3H).
C
13
(s, 3H). C NMR (150 MHz, CDCl ) δ 195.38, 172.36, 142.46,
3
NMR (150 MHz, CDCl ) δ 195.02, 172.22, 148.16, 143.27,
3
1
36.51, 135.67, 129.06, 128.43, 127.55, 126.26, 123.50, 120.01,
1
2
2
28.40, 124.44, 117.64, 115.52, 56.86, 55.86, 29.91, 23.28,
1
16.02, 57.17, 55.93, 46.31, 23.32. HRMS (ESI) calcd for
+
2.48. HRMS (ESI) calcd for C H N O [M+Na] :
+
13
14
4
2
C H N O [M+Na] : 343.1163, found: 343.1164.
18
16
4
2
81.1009, found: 281.1001.
3
-(Azidomethyl)-1-methyl-3-phenylquinoline-2,4(1H,3H)-di-
one (2s). Red liquid (21 mg, 23% yield). R (Petroleum ether:
f
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5
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RESEARCH ARTICLE
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1
Ethyl acetate=3:1): 0.50. H NMR (600 MHz, CDCl ) δ 8.01–
7
3-((5-((8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-
3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-
cyclopenta[a]phenanthren-17-yl)-1H-1,2,3-triazol-1-yl)
methyl)-1,3-dimethylquinoline-2,4(1H,3H)-dione (7). White
3
.99 (m, 1H), 7.59–7.56 (m, 1H), 7.30–7.27 (m, 3H), 7.23–7.22
m, 2H), 7.16–7.13 (m, 1H), 7.11 (d, J=8.3 Hz, 1H), 4.26 (d,
J=11.6 Hz, 1H), 4.16 (d, J=11.6 Hz, 1H), 3.58 (s, 3H).
(
1
3
C
NMR (150 MHz, CDCl ) δ 193.16, 169.55, 142.63, 136.20,
solid (162 mg, 97% yield). R (Ethyl acetate): 0.35. mp 239–
3
f
1
134.01, 129.33, 128.84, 128.26, 126.71, 123.47, 121.37, 115.03,
240°C. H NMR (600 MHz, CDCl ) δ 8.05–7.99 (m, 1H), 7.64–
3
6
6.95, 54.96, 30.28. HRMS (ESI) calcd for C H N O [M+
7.62 (m, 1H), 7.39 (d, J=3.2 Hz, 1H), 7.18–7.16 (m, 2H), 5.70
(d, J=6.2 Hz, 1H), 5.03–4.96 (m, 2H), 3.46 (d, J=5.8 Hz, 3H),
17
14
4
2
+
Na] : 329.1009, found: 329.1005.
2
4
5
.73 (d, J=30.3 Hz, 1H), 2.43–2.20 (m, 5H), 2.03 (d, J=
.4 Hz, 1H), 1.95–1.93 (m,1H), 1.86–1.63 (m, 4H), 1.56 (d, J=
3
-Azido-N-(2-cyanophenyl)-2-methyl-2-(phenylselanyl)
propanamide (3). Yellow soild (76 mg, 66% yield). Rf
.8 Hz, 3H), 1.44–1.31 (m, 5H), 1.15 (d, J=4.1 Hz, 3H), 0.99
1
(
Petroleum ether: Ethyl acetate=5:1): 0.36. mp 65–66°C. H
13
(d, J=3.7 Hz, 3H), 0.66–0.59 (m, 1H), 0.33–0.22 (m, 1H). C
NMR (600 MHz, CDCl ) δ 8.75 (s, 1H), 8.31 (d, J=8.4 Hz,
3
NMR (150 MHz, CDCl ) δ 199.54, 194.25, 194.13, 171.59,
1
1
3
1
7
1
1
1
H), 7.62–7.57 (m, 4H), 7.42–7.38 (m, 1H), 7.32–7.29 (m, 2H),
71.49, 171.29, 153.46, 153.40, 143.13, 143.09, 136.55, 136.51,
28.55, 128.52, 123.79, 123.33, 123.32, 122.18, 119.37, 115.15,
.21–7.18 (m, 1H), 3.92 (d, J=12.6 Hz, 1H), 3.69 (d, J=
1
3
2.6 Hz, 1H), 1.70 (s, 3H). C NMR (150 MHz, CDCl ) δ
3
115.14, 81.96, 81.89, 56.35, 56.29, 53.30, 53.29, 53.09, 53.06,
70.65, 140.34, 137.58, 134.20, 132.28, 129.98, 129.44, 125.32,
4
3
2
8.75, 48.73, 46.74, 46.73, 38.56, 37.62, 37.56, 36.20, 36.19,
5.61, 35.59, 33.94, 32.81, 32.51, 32.50, 31.49, 30.00, 24.33,
24.35, 120.95, 116.26, 102.26, 58.12, 51.31, 22.54. HRMS
+
(ESI) calcd for C H N OSe [M+Na] : 408.0334, found:
17
15
5
4.30, 23.63, 23.57, 20.54, 20.51, 17.38, 17.36, 14.16. HRMS
4
08.0331.
+
(ESI) calcd for C H N O [M+Na] : 579.2942, found:
33
40
4
4
3-(Azidomethyl)-4-hydroxy-1,3-dimethyl-3,4-dihydroquino-
579.2940.
lin-2(1H)-one (4). Yellow liquid (33.2 mg, 45% yield). R
f
1
(Petroleum ether: Ethyl acetate=1:1): 0.33.
H NMR
(
7
1
600 MHz, CDCl ) δ 7.53–7.51 (m, 1H), 7.33–7.31 (m, 1H),
3
Acknowledgements
.17–7.14 (m, 1H), 6.99 (d, J=7.8 Hz, 1H), 5.10 (d, J=5.9 Hz,
H), 3.95 (d, J=12.1 Hz, 1H), 3.47 (d, J=12.1 Hz, 1H), 3.36
This work was supported by the National Natural Science
Foundation of China (21801007).
1
3
(s, 3H), 2.79 (d, J=6.1 Hz, 1H), 0.94 (s, 3H). C NMR
(
150 MHz, CDCl ) δ 171.65, 137.29, 128.56, 127.57, 125.47,
3
1
23.73, 114.16, 67.93, 54.15, 47.82, 30.13, 14.04. HRMS (ESI)
+
References
calcd for C H N O [M+Na] : 269.1009, found: 269.1008.
12
14
4
2
White solid (33.2 mg, 45% yield). R (Petroleum ether: Ethyl
f
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acetate=1:1): 0.25. mp 84–85°C. H NMR (600 MHz, CDCl )
3
δ 7.40–7.36 (m, 1H), 7.32–7.31 (m, 1H), 7.11–7.08 (m, 1H),
6
, 2696–2718; c) P. Thirumurugan, D. Matosiuk, K.
7
3
3
1
1
2
.03 (d, J=8.1 Hz, 1H), 4.51 (s, 1H), 3.94 (d, J=12.3 Hz, 1H),
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.70 (d, J=12.3 Hz, 1H), 3.36 (s, 3H), 2.41 (s, 1H), 1.03 (s,
13
H). C NMR (150 MHz, CDCl ) δ 171.82, 138.79, 129.91,
3
29.04, 125.40, 123.46, 114.85, 72.04, 54.21, 46.55, 29.67,
[2] a) S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew.
+
8.76. HRMS (ESI) calcd for C H N O [M+Na] :
12
14
4
2
Chem. Int. Ed. 2005, 44, 5188–5240; Angew. Chem.
69.1009, found: 269.1007.
2
005, 117, 5320–5374; b) E. Gwilherm, Angew. Chem.
4-Hydroxy-1,3-dimethylquinolin-2(1H)-one (5). White solid
Int. Ed. 2010, 35, 6025–6025.
(
0
1
52 mg, 92% yield). R (Petroleum ether: Ethyl acetate=1:1):
[3] For selected works, see: a) C.-H. Tang, N. Jiao, J. Am.
Chem. Soc. 2012, 134, 18924–18927; b) X.-Y. Huang,
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f
1
.19. mp 212–213°C. H NMR (600 MHz, DMSO) δ 10.09 (s,
H), 7.97 (d, J=7.9 Hz, 1H), 7.57 (t, J=7.8 Hz, 1H), 7.47 (d,
J=8.3 Hz, 1H), 7.24 (t, J=7.5 Hz, 1H), 3.59 (s, 3H), 2.05 (s,
3
1
HRMS (ESI) calcd for C H NO [M+Na] : 212.0682, found:
2
1
37, 5300–5303; c) A. Sharma, J. F. Hartwig, Nature
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H). C NMR (150 MHz, DMSO) δ 163.65, 156.37, 138.46,
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015, 517, 600–604; d) X.-Y. Huang, J. T. Groves, ACS
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1152–1176; h) S.-J. Shen, C.-L. Zhu, D.-F. Lu, H. Xu,
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Chem. Front. 2019, 6, 2934–2938; j) R. Sala, C. Loro, F.
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11
11
2
12.0683.
1
,3-Dimethyl-3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)
quinoline-2,4(1H,3H)-dione (6). White solid (102 mg, 98%
yield). R (Petroleum ether: Ethyl acetate=1:1): 0.40. mp 151–
1
(
7
2
1
1
3
3
f
1
52°C. H NMR (600 MHz, CDCl ) δ 8.03–8.02 (m, 1H), 7.80
3
s, 1H), 7.71 (d, J=7.7 Hz, 2H), 7.61–7.56 (m, 1H), 7.34 (t, J=
.6 Hz, 2H), 7.28–7.24 (m, 1H), 7.16–7.12 (m, 2H), 5.04 (s,
1
3
H), 3.44 (s, 3H), 1.55 (s, 3H). C NMR (150 MHz, CDCl ) δ
3
94.24, 171.63, 147.72, 143.10, 136.49, 130.47, 128.75, 128.51,
28.08, 125.64, 123.30, 120.72, 119.43, 115.21, 56.29, 53.28,
+
0.00, 24.27. HRMS (ESI) calcd for C H N O [M+Na] :
20
18
4
2
1
402–1406; l) L.-B. Niu, C.-Y. Jiang, Y.-W. Liang, D.-D.
69.1322, found: 369.1317.
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6
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© 2021 Wiley-VCH GmbH
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These are not the final page numbers!

RESEARCH ARTICLE
Metal-Free Organoselenium-Enabled Radical Relay
Azidation-Carbocyclization
Adv. Synth. Catal. 2021, 363, 1–8
X. Wang, S. Guo, Y. Zhang, Z. Zhang*, G. Zhang*, Y. Ye, K.
Sun*