A Formal [3+2] Annulation of β-Oxoamides and 3-Alkyl- or 3-Aryl-Substituted Prop-2-Ynyl Sulfonium Salts: Substrate-Controlled Chemoselective Synthesis of Substituted γ-Lactams and Furans

Article abstract of DOI:10.1002/adsc.201900693

A substrate-controlled synthesis of substituted γ-lactams and furans has been developed via a formal [3+2] annulation of β-oxoamides and 3-alkyl/arylprop-2-ynyl sulfonium salts in the presence of cesium carbonate in a chemoselective manner. This novel pro

Full text of DOI:10.1002/adsc.201900693

Title: A Formal [3+2] Annulation of β-Oxoamides and 3-Alkyl/
arylprop-2-ynyl Sulfonium Salts: Substrate-Controlled
Chemoselective Synthesis of Substituted γ-Lactams and Furans
Authors: Bicheng Deng, Bhujanga Rao chitturi, RUI ZHANG, Jiacheng
Li, YONGJIU liang, Yanning Zhao, Ming Gao, and Dewen
Dong
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201900693
Link to VoR: http://dx.doi.org/10.1002/adsc.201900693

10.1002/adsc.201900693
Advanced Synthesis & Catalysis
FULL PAPER
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
A Formal [3+2] Annulation of β-Oxoamides and 3-Alkyl- or 3-
Aryl-Substituted Prop-2-ynyl Sulfonium Salts: Substrate-
Controlled Chemoselective Synthesis of Substituted γ-Lactams
and Furans
Bicheng Deng,a,b Chitturi Bhujanga Rao,b Rui Zhang,b Jiacheng Li,b Yongjiu Liang,b
Yanning Zhao,*,a Ming Gao,a,b and Dewen Dong*, a,b
a
Key Laboratory of Preparation and Application of Environmental Friendly Materials of the Ministry of Education, Jilin
Normal University, Changchun 130103, China.
Key Laboratory of High-Performance Synthetic Rubber and its Composites, Changchun Institute of Applied Chemistry,
b
Chinese Academy of Sciences, Changchun, 130022, China.
Fax: (+86)-431-85262740; phone: (+86)-431-85262676;
Email Address: yanningzhao@jlnu.edu.cn; dwdong@ciac.ac.cn
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract. A substrate-controlled synthesis of substituted γ- available starting materials, mild reaction conditions,
lactams and furans has been developed via a formal [3+2] simple execution, and good to excellent yields of products.
annulation of β-oxoamides and 3-alkyl/arylprop-2-ynyl
sulfonium salts in the presence of cesium carbonate in a
chemoselective manner. This novel protocol features easily
Keywords: Annulation; Furans; γ-Lactams; β-Oxoamides;
Sulfur ylides
occurring furanoterpenoids.[9] Recently, Huang et al.
reported the reactions of prop-2-ynyl sulfonium salts
with a variety of functionalized arylsulfonamides, by
which a series of five-membered aza-heterocycles
were obtained and prop-2-ynylsulfonium salts were
proved to be versatile C1 and C2 synthons. [10]
Introduction
Over the past decades, the heterocycles containing γ-
lactam or furan skeletons have attracted considerable
attention for their presence in numerous natural
products and designed molecules along with diverse
bioactivities, and widely used in a number of areas
ranging from organic synthesis, medicinal chemistry,
agrochemistry, to polymer chemistry.[1-3] In this
context, the development of facile and efficient
approaches for the synthesis of such five-membered
heterocycles through the construction of C−X (X = N,
O) bond, in particular from easily available open-
chain precursors with flexible substituent patterns,
has long been an important topic of organic chemistry
and continues to be an active research area.[4, 5]
On the other hand, sulfur ylides have emerged as
efficient nucleophilic alkylidene-transfer reagents (C1
and C2 synthons) in synthetic chemistry, and found
wide applications in the preparation of carbo- and
heterocycles, including cyclopropanes, epoxides,
aziridines, pyrazoles, and pyrrolidines.[6-8] In the early
1990s, Kanematsu and coworkers developed a
convenient synthetic approach for fused 3-
methylfuran via a formal [3+2] annulation of 1,3-
dicarbonyl compounds and prop-2-ynyl sulfonium
salts (Scheme 1a), and later applied this furannulation
strategy in the total synthesis of some naturally
1
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10.1002/adsc.201900693
Advanced Synthesis & Catalysis
Scheme 1. Sulfur ylide-mediated annulation reactions.
the structure of 3aa was unambiguously confirmed by
X-ray single crystal analysis (Figure 1).
During the course of our studies on the synthesis
and applications of varied β-oxoamides and their
derivatives, [11] we achieved efficient synthesis of γ-
lactams via a formal [4+1] annulation of α,α-dialkyl-
β-oxo amides and trimethyl sulfoxonium iodide in the
presence of NaH (Scheme1b)[12] and synthesis of
substituted pyridin-2(1H)-ones via a formal [4+2]
annulation of α-acyl acrylamides and cyanomethyl
sulfonium salt in the presence of cesium carbonate
(Cs2CO3), respectively.[13] Inspired by these results
and our continued research interest in developing new
synthetic methods for highly valuable heterocycles,
we set out to explore the reactions of β-oxoamides
with 3-alkyl/arylprop-2-ynyl sulfonium salts. After a
series of detailed investigation, we achieved efficient
synthesis of substituted γ-lactams and furans under
very mild conditions (Scheme 1c). Herein, we wish to
report our experimental results and present a
proposed mechanism involved in the formal [3+2]
annulation reactions.
Having established the optimal conditions for the
formal [3+2] annulation process, we aimed to
determine its scope and limitation with respect to the
substituents R1, R2 and R3 of α-monosubstituted β-
oxoamides 1. Thus, a series of reactions of 1 and 2
were carried out in the presence of Cs2CO3 in DMF at
room temperature, and some of the results are
summarized in Table 1.
Table 1 Formal [3+2] annulation of α-monosubstituted β-
oxoamides 1 and 3-alkyl/arylprop-2-ynyl sulfonium salts
2[a]
Results and Discussion
The substrates, α-monosubstituted β-oxoamides 1,
were prepared from commercially available alkyl
bromides and α-unsubstituted β-oxoamides in the
presence of potassium carbonate (K2CO3) in high
yields according to a reported procedure.[11a] Thus,
the reaction of 2-benzyl-3-oxo-N-phenylbutanamide
1a and prop-2-ynyl sulfonium salt 2a (1.0 equiv.) was
first attempted in the presence of Cs2CO3 (1.0 equiv.)
in N,N-dimethylformamide (DMF) at room
temperature. The reaction proceeded smoothly as
indicated by TLC results and furnished a white solid
after work-up and purification of the resulting
mixture by column chromatography. The product was
characterized as 3-acetyl-3-benzyl-4-methylene-1-
phenylpyrolidin-2-one 3aa on the basis of its spectral
and analytical data (Scheme 2).
Scheme 2. Reaction of α-monosubstituted β-oxoamide 1a
and prop-2-ynyl sulfonium salt 2a.
We then briefly examined the effect of different
base (Cs2CO3, K2CO3, NaOH, NaOEt, NEt3, and
DBU), the feed ratio of 1a/base/2a, solvents (DMF,
DMSO, DCM, toluene, and acetonitrile), and reaction
temperature on the success of the formal [3+2]
annulation reaction to 3aa (for detailed experiments,
see Supporting Information). The experimental
results revealed that Cs2CO3 was the most effective
base, and the optimal reaction conditions were
obtained when 1a and 2a (1.5 equiv.) were treated
with Cs2CO3 (1.5 equiv.) in DMF at room
temperature, whereby the yield of γ-lactam 3aa
reached 93% (Table 1). It should be mentioned that
[a]
Reagents and conditions: 1 (1.0 mmol), 2 (1.5 mmol),
Cs2CO3 (1.5 mmol), DMF (5.0 mL), rt. Isolated yields of 3
and reaction times are given.
2
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10.1002/adsc.201900693
Advanced Synthesis & Catalysis
sulfonium salts 2 under the identical conditions as for
3aa. The reaction of 3-oxo-N-phenylbutanamide 1p
and 2a was then performed in the presence of Cs2CO3
in DMF at room temperature. A reddish solid was
obtained after work-up and purification of the
resulting mixture by column chromatography, which
was characterized as 1-[4-methyl-2-(phenylamino)
furan-3-yl]ethan-1-one 4pa on the basis of its spectral
and analytical data (Scheme 3), and the
corresponding γ-lactam 3pa was not even detected. In
the same fashion, a series of α-unsubstituted β-
oxoamides 1q-w bearing varied N-aryl amide groups
(CONHR1) and alkyl, aryl or methoxy R2 groups
reacted with 2a under the identical conditions
afforded the corresponding substituted furans 4qa-wa
in good to high yields. The substituents on the phenyl
rings of amides 1 showed little influence on the
reactions as both electron-donating and electron-
withdrawing groups are well-tolerated. Notably,
furans 4xa and 4ya were obtained in high yields from
the corresponding β-oxoamides 1x and 1y bearing a
butyl or benzyl R1 group. The versatility of this furan
synthesis was further evaluated by treatment of 1p
with prop-2-ynyl sulfonium salts 2b and 2c in the
presence of Cs2CO3, respectively.
Figure 1. ORTEP drawing of 3aa.
It was observed that all the reactions of α-benzyl β-
oxoamides 1b-f bearing varied electron-withdrawing
or electron-donating substituents on their aryl R1
groups and 2a proceeded smoothly to deliver the
corresponding γ-lactams 3ba-fa in excellent yields.
Interestingly, the reaction of α-benzyl β-oxoamide 1g
bearing a butyl R1 group resulted in a complex
mixture, in which 3ga was not even detected. Similar
results were obtained when N-benzyl β-oxoamide 1h
was subjected to the identical conditions. The validity
of the formal [3+2] annulation is proved to be
suitable for α-benzyl β-oxoamides 1i and 1j bearing a
phenyl or methoxy R2 group to afford the
corresponding γ-lactams 3ia and 3ja, respectively.
The versatility of this lactam synthesis was further
evaluated by performing the reactions of 1k-o bearing
varied R3 groups and 2a.
Notably, the reaction of 1a and but-2-ynyl
sulfonium salt 2b was carried out to furnish a
product, which was characterized as (Z)-3-acetyl-3-
benzyl-4-ethylidene-1-phenylpyrrolidin-2-one 3ab,
and its (E)-isomer 3ab' was not even detected. The Z-
configuration of 3ab was established by NOESY
spectra (see Supporting Information). The detailed
2D NMR analysis clearly indicated that the reaction
of 1a and 2b proceeded in a highly stereoselective
manner. Similarly, (Z)-3-acetyl-3-benzyl-4-benzylide-
ne-1-phenylpyrrolidin-2-one 3ac was synthesized
from 1a and 3-phenylprop-2-yn-1-yl sulfonium salt
2c.
Table 2 Formal [3+2] annulation of α-unsubstituted β-
oxoamides 1 and prop-2-ynyl sulfonium salts 2[a]
The results shown above reveal that benzyl, allyl,
alkynyl, ester, cyano, and varied N-aryl amide groups
with chloro, methoxy or nitro substituent on benzene
ring are well-tolerated under the basic reaction
conditions, which demonstrated the efficiency and
synthetic value of the transformation of α-
monosubstituted β-oxoamides 1 to γ-lactams 3. By
contrast with Kanematsu’s work,[9a] the amide group
of 1 preferentially reacts with prop-2-ynyl sulfonium
salt 2 over the acyl group of 1 in the present work
showed high chemoselectivity of the formal [3+2]
annulation process.
Scheme 3. Reaction of α-unsubstituted β-oxoamide 1p and
prop-2-ynylsulfonium salt 2a.
[a]
Reagents and conditions: 1 (1.0 mmol), 2 (1.5 mmol),
Cs2CO3 (1.5 mmol), DMF (5.0 mL), rt. Isolated yields of 4
and reaction times are given.
To further expand the scope of the formal [3+2]
annulation, we intended to examine the reactions of
α-unsubstituted β-oxoamides 1 and prop-2-ynyl
3
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10.1002/adsc.201900693
Advanced Synthesis & Catalysis
By comparing the results shown in Table 1 and
Scheme 4. Plausible mechanism for the formal [3+2]
annulation reactions.
Table 2, it is easy to conclude that the nature of α-
substituent R3 of β-oxoamides 1 played a critical role
in their reactions with prop-2-ynyl sulfonium salts 2
to deliver different products, i.e. γ-lactams 3 and
furans 4. Actually, controlling the ambident reactivity
of an amide group (CONHR) to form C−N or C−O
bond remains a challenging issue in the use of amides
in organic transformations.[14] In the present work, we
provided an alternative protocol to achieve the
chemoselective C−N or C−O bond formation simply
by varying the α-substituent R3 of the substrate β-
oxoamide 1.[15]
Conclusions
In summary, we have described herein a formal [3+2]
annulation reaction of β-oxoamides 1 and 3-alkyl/
arylprop-2-ynyl sulfonium salts 2 in the presence of
Cs2CO3 at room temperature, and provided a
substrate-controlled synthesis of substituted γ-lactams
and furans. The readily available starting materials,
mild reaction conditions, simple execution, good to
excellent yields of products, and high chemo- and
stereoselectivity make this protocol very attractive to
academic research and practical applications. Further
studies on the mechanism, extension and utilization
of the formal [3+2] annulation are currently
underway in our laboratory.
On the basis of the obtained results together with
reported literature,[6-10] a mechanism is proposed for
the formal [3+2] annulation reaction of β-oxoamides
1 and 3-alkyl/arylprop-2-ynyl sulfonium salt 2 as
depicted in Scheme 4. In the presence of Cs2CO3, β-
oxoamide 1 is quickly deprotonated to a carboanion
A, and meanwhile prop-2-ynyl sulfonium salt 2 is
isomerized to an allienic sulfonium salt B.[9,10]
Subsequent conjugated addition of the carboanion A
to B generates intermediate C,[10a] which undergoes a
facile proton shift to give N-centered or O-centered
intermediate depending on the nature of α-substituent
R3 of β-oxoamide 1. For both electronic and steric
effects, intermediate D is a favorable form when R3 is
not H, wherein the nitrogen anion is particularly
stabilized by the adjacent carbonyl and R1 groups.
Then, intramolecular N-alkylation of D takes place to
deliver γ-lactam 3 along with the elimination of
dimethyl sulfide.[8e,16] As such, it is not hard to
understand why α-benzyl β-oxoamides 1g and 1h
bearing a butyl or benzyl R1 group showed different
reaction behavior from other α-monosubstituted β-
oxoamides 1 with N-aryl amide groups. While R3 is
H, a planar conjugated enolate anion E is favored for
the formation of intramolecular N−H···O hydrogen
bond,[17] and the charge on the O-atom is easily
Experimental Section
General
All reagents were purchased from commercial sources and
1
used without purification, unless otherwise indicated. H
o
NMR and 13C NMR spectra were recorded at 25 C at 300
MHz (or 400 MHz) and 75 MHz (or 100 MHz),
respectively, with TMS as internal standard. IR spectra
(KBr) were recorded on FTIR-spectrophotometer in the
range of 400-4000 cm-1. High resolution mass spectra
(ESI-Q-TOF/HRMS) were recorded on
a
mass
spectrometer. Melting points were recorded on a TECH X-
4 micro-melting point apparatus. All reactions were
monitored by TLC with GF254 silica gel-coated plates.
The products were isolated by column chromatography on
silica gel (300−400 mesh).
delocalized within this system.[18] Enolate
E
undergoes intramolecular O-alkylation to afford
dihydrofuran F,[19] followed by isomerization through
a 1,3-H shift to give the final trisubstituted furan 4.[20]
General procedure for the synthesis of γ-
lactams 3 (3aa as an example):
To a mixture of prop-2-ynyl sulphonium salt 2a (271.6 mg,
1.5 mmol) and Cs2CO3 (488.7 mg, 1.5 mmol) in DMF (5.0
mL) was added 2-benzyl-3-oxo-N-phenylbutanamide 1a
(267.3 mg, 1.0 mmol). The resulting mixture was stirred at
room temperature for 0.5 h, which was then poured
into aqueous HCl solution (0.1 N, 50 mL) and extracted
with CH2Cl2 (3 × 20 mL). The combined organic phase
was washed with water (3 × 30 mL), dried over anhydrous
MgSO4, filtered, and evaporated in vacuo. The crude
product was purified by column chromatography (silica gel,
petroleum ether/ethyl acetate = 6:1) to give 3aa as a white
solid (284.0 mg, 93%).
Analytical data of γ-lactams 3
3-Acetyl-3-benzyl-4-methylene-1-phenylpyrrolidin-2-
one (3aa)
4
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10.1002/adsc.201900693
Advanced Synthesis & Catalysis
1
White solid (284.0 mg, 93%), m.p. 125-126 ºC; H NMR
(300 MHz, CDCl3): δ 7.32-7.39 (m, 4H), 7.16-7.21 (m,
6H), 5.37 (t, J = 2.1 Hz, 1H), 5.26 (t, J = 2.4 Hz, 1H), 4.23
(dt, J1 = 13.8 Hz, J2 = 2.1 Hz, 1H), 3.43-3.50 (m, 2H), 3.24
(d, J = 13.2 Hz, 1H), 2.25 (s, 3H); 13C NMR (75 MHz,
CDCl3): 201.3, 171.7, 139.5, 137.9, 135.8, 130.2, 129.0,
128.1, 126.9, 125.7, 120.8, 112.0, 69.5, 53.0, 40.4, 26.9; IR
(KBr): 3030.7, 2924.5, 1714.5, 1687.0, 1661, 1597.7,
1495.1, 1401.8, 907.3, 766.6, 703.2 cm-1; HRMS (ESI)
m/z: calcd. for C20H19NO2 [M + Na]+: 328.1308, Found:
328.1306.
m/z: calcd. for C21H21NO3 [M + Na]+: 358.1414, Found:
358.1402.
3-Acetyl-3-benzyl-4-methylene-1-(2-nitrophenyl)
pyrrolidin-2-one (3ea)
1
White solid (329.3 mg, 94%), m.p. 128-129 ºC; H NMR
(300 MHz, CDCl3): δ 8.12-8.13 (m, 1H), 7.98-8.05 (m,
2H), 7.53 (t, J = 8.4 Hz, 1H), 7.14 (s, 5H), 5.44 (t, J = 2.4
Hz, 1H), 5.32 (t, J = 2.7 Hz, 1H), 4.29 (dt, J1 = 13.8 Hz, J2
= 1.8 Hz, 1H), 3.43-3.51 (m, 2H), 3.27 (d, J = 13.8 Hz,
1H), 2.26 (s, 3H); 13C NMR (75 MHz, CDCl3): 200.6,
172.5, 148.5, 138.9, 138.5, 135.4, 130.0, 129.9, 128.2,
127.2, 125.9, 119.9, 114.6, 112.7, 69.5, 52.6, 40.9, 27.1; IR
(KBr): 2930.5, 2873.5, 1712.5, 1694.2, 1527.5, 1390.8,
1353.1, 908.0, 733.5 cm-1; HRMS (ESI) m/z: calcd. for
C20H18N2O4 [M + Na]+: 373.1159, Found: 373.1157.
Crystal data for 3aa: C20H19NO2, White crystal, M =
305.36, orthorhombic, P212121, a = 7.6446(5) Ǻ, b =
13.1672(8) Ǻ, c = 16.3981(10) Ǻ, α = 90.00o, β = 90.00°, γ
= 90.00o, V = 1650.60(18) Ǻ3, Z = 4, T = 273.15 K, F000 =
648.0, R = 0.0388 (3056), wR2 = 0.1037 (3373). CCDC
1910704 contains the supplementary crystallographic data
for this paper. These data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via
www.ccdc.cam.ac.uk/data_request/cif.
3-Acetyl-3-benzyl-1-(2,4-dimethylphenyl)-4-methylene
pyrrolidin-2-one (3fa)
1
White solid (310.1 mg, 93%), m.p. 96-97 ºC; H NMR
(300 MHz, CDCl3): δ 7.26 (s, 5H), 7.02 (s, 1H), 6.93 (d, J
= 7.8 Hz, 1H), 6.34 (d, J = 7.8 Hz, 1H), 5.36 (t, J = 2.4 Hz,
1H), 5.31 (t, J = 2.7 Hz, 1H), 4.05 (dt, J1 = 14.4 Hz, J2 =
2.1 Hz, 1H), 3.53 (dt, J1 = 14.1 Hz, J2 = 2.1 Hz, 1H), 3.42
(d, J = 13.2 HZ, 1H), 3.24 (d, J = 13.2 Hz, 1H), 2.31 (s,
3H), 2.28 (s, 3H), 2.01 (s, 3H); 13C NMR (75 MHz,
CDCl3): 201.4, 171.4, 140.9, 138.2, 136.2, 135.3, 133.5,
131.8, 130.7, 128.2, 127.6, 127.0, 126.0, 112.0, 68.3, 54.6,
40.3, 27.1, 21.0, 17.8; IR (KBr): 3035.4, 2918.5, 2816.8,
1710.3, 1698.2, 1655.9, 1500.9, 1413.3, 912.1, 711.4 cm-1;
HRMS (ESI) m/z: calcd. for C22H23NO2 [M + Na]+:
356.1621, Found:356.1618.
3-Acetyl-3-benzyl-4-methylene-1-(p-tolyl)pyrrolidin-2-
one (3ba)
1
White solid (293.8 mg, 92%), m.p. 81-82 ºC; H NMR
(300 MHz, CDCl3): δ 7.22-7.26 (m, 2H), 7.13-7.16 (m,
7H), 5.35 (t, J = 2.1 Hz, 1H), 5.24 (t, J = 2.4 Hz, 1H), 4.20
(dt, J1 = 13.2 Hz, J2 = 2.1 Hz, 1H), 3.44 (d, J = 13.2 Hz,
2H), 3.23 (d, J = 13.2 Hz, 1H), 2.32 (s, 3H), 2.25 (s, 3H);
13C NMR (75 MHz, CDCl3): 201.5, 171.5, 139.7, 135.9,
135.5, 135.4, 130.3, 129.6, 128.1, 126.9, 120.9, 111.9, 69.4,
53.1, 40.4, 26.9, 21.0; IR (KBr): 3034.7, 2924.4, 2869.7,
1711.5, 1686.3, 1661.2, 1511.0, 1394.1, 906.5, 708.1 cm-1;
HRMS (ESI) m/z: calcd. for C21H21NO2 [M + Na]+:
342.1465, Found: 342.1461.
3-Benzoyl-3-benzyl-4-methylene-1-phenylpyrrolidin-2-
one (3ia)
1
3-Acetyl-3-benzyl-1-(4-chlorophenyl)-4-methylene
pyrrolidin-2-one (3ca)
White solid (334.4 mg, 91%), m.p. 115-116 ºC; H NMR
(300 MHz, CDCl3): δ 7.78 (d, J = 7.2 Hz, 2H), 7.49 (t, J =
7.2 Hz, 1H), 7.31-7.39 (m, 4H), 7.15-7.26 (m, 8H), 5.32 (t,
J = 2.1 Hz, 1H), 5.22 (t, J = 2.1 Hz, 1H), 4.27 (dt, J1 =
13.8 Hz, J2 = 1.8 Hz, 1H), 3.61 (d, J = 12.9 Hz, 1H), 3.41-
3.48 (m, 2H); 13C NMR (75 MHz, CDCl3): 194.9, 172.0,
140.9, 137.9, 135.8, 135.4, 132.7, 130.5, 129.0, 128.6,
128.5, 128.1, 127.0, 125.6, 120.9, 112.0, 67.3, 52.9, 42.9;
IR (KBr): 2929.7, 2872.5, 1695.6, 1660.1, 1597.2, 1500.8,
1445.9, 1389.1, 914.3, 753.2 cm-1; HRMS (ESI) m/z: calcd.
for C25H21NO2 [M + Na]+: 390.1465, Found: 390.1451.
1
White solid (309.2 mg, 91%), m.p. 100-101 ºC; H NMR
(300 MHz, CDCl3): δ 7.28-7.35 (m, 4H), 7.15 (s, 5H), 5.37
(t, J = 2.4 Hz, 1H), 5.26 (t, J = 2.4 Hz, 1H), 4.19 (dt, J1 =
13.2 Hz, J2 = 2.4 Hz, 1H), 3.37-3.45 (m, 2H), 3.23 (d, J =
13.2 Hz, 1H), 2.24 (s, 3H); 13C NMR (75 MHz, CDCl3):
201.1, 171.9, 139.1, 136.4, 135.6, 130.8, 130.1, 129.1,
128.1, 127.0, 121.7, 112.2, 69.4, 52.8, 40.6, 27.0; IR
(KBr): 3063.8, 2974.1, 2924.6, 1714.5, 1687.4, 1661.9,
1495.8, 1454.6, 1395.2, 907.5, 830.2, 702.2 cm-1; HRMS
(ESI) m/z: calcd. for C20H18ClNO2 [M + Na]+: 362.0918,
Found: 362.0920.
Methyl 3-benzyl-4-methylene-2-oxo-1-
phenylpyrrolidine-3-carboxylate (3ja)
Yellow oil (244.2 mg, 76%); 1H NMR (400 MHz, DMSO‑
d6): δ 7.49 (d, J = 8.4 Hz, 2H), 7.35 (t, J = 8.4 Hz, 2H),
7.16-7.20 (m, 6H), 5.40-5.41 (m, 2H), 4.46 (d, J = 14.4 Hz,
1H), 3.70 (s, 3H), 3.60 (d, J = 14.4 Hz, 1H), 3.41 (d, J =
13.6 Hz, 1H), 3.29 (d, J = 13.6 Hz, 1H); 13C NMR (100
MHz, CDCl3): 170.43, 170.40, 139.9, 138.1, 135.2, 130.5,
128.9, 128.1, 127.0, 125.5, 120.9, 111.2, 62.8, 53.1, 52.7,
40.6; IR (KBr): 3031.6, 2952.9, 2873.9, 1742.7, 1665.1,
1597.9, 1495.8, 1465.6, 1397.3, 1240.9, 909.5,763.0 cm-1;
HRMS (ESI) m/z: calcd. for C20H19NO3 [M + Na]+:
344.1257, Found: 344.1254.
3-Acetyl-3-benzyl-1-(4-methoxyphenyl)-4-methylene
pyrrolidin-2-one (3da)
1
White solid (308.6 mg, 92%), m.p. 116-117 ºC; H NMR
(300 MHz, CDCl3): δ 7.21 (d, J = 9.0 Hz, 2H), 7.18 (m,
5H), 6.86 (d, J = 9.0 Hz, 2H), 5.35 (t, J = 2.1 Hz, 1H),
5.25 (t, J = 2.1 Hz, 1H), 4.18 (dt, J1 = 14.1 Hz, J2 = 1.8 Hz,
1H), 3.79 (s, 3H), 3.39-3.46 (m, 2H), 3.22 (d, J = 13.2 Hz,
1H), 2.25 (s, 3H); 13C NMR (75 MHz, CDCl3): 201.5,
171.4, 157.4, 139.8, 135.9, 130.9, 130.3, 128.1, 126.9,
122.8, 114.2, 111.9, 69.2, 55.5, 53.4, 40.4, 26.9; IR (KBr):
3000.9, 2957.7, 2926.3, 1710.8, 1691.4, 1516.1, 1461.7,
1401.4, 1250.8, 1027.9, 833.1, 705.1 cm-1; HRMS (ESI)
3-Acetyl-3-ethyl-4-methylene-1-phenylpyrrolidin-2-one
(3ka)
5
This article is protected by copyright. All rights reserved.

10.1002/adsc.201900693
Advanced Synthesis & Catalysis
Yellowish oil (214.1 mg, 88%); 1H NMR (300 MHz,
116.7, 114.4, 64.8, 52.8, 25.9, 22.7; IR (KBr): 3066.2,
CDCl3): δ 7.72 (d, J = 8.1 Hz, 2H), 7.43 (t, J = 8.1 Hz, 2H), 2886.8, 2243.5, 1715.2, 1687.3, 1598.4, 1502.2, 1400.5,
7.22 (t, J = 7.5 Hz, 1H), 5.40 (t, J = 2.1 Hz, 1H), 5.16 (t, J
= 2.1 Hz, 1H), 4.62 (dt, J1 = 14.1 Hz, J2 = 2.1 Hz, 1H),
4.50 (dt, J1 = 14.1 Hz, J2 = 2.1 Hz, 1H), 2.20 (s, 3H), 1.95-
2.07 (m, 2H), 0.88 (t, J = 7.5 Hz, 3H); 13C NMR (75 MHz,
CDCl3): 201.9, 172.0, 139.0, 138.4, 129.2, 125.4, 120.1,
111.5, 68.9, 52.8, 27.4, 26.7, 8.5; IR (KBr): 3065.1, 2970.8,
2879.8, 1714.8, 1598.0, 1504.0, 1392.8, 909.6, 760.0 cm-1;
HRMS (ESI) m/z: calcd. for C15H17NO2 [M + Na]+:
266.1151, Found: 266.1147.
903.0, 743.3, 639.1 cm-1; HRMS (ESI) m/z: calcd. for
C15H14N2O2 [M + Na]+: 277.0947, Found: 276.0952.
(Z)-3-Acetyl-3-benzyl-4-ethylidene-1-phenylpyrrolidin-
2-one (3ab)
1
White solid (268.3 mg, 84%), m.p. 119-120 ºC; H NMR
(300 MHz, CDCl3): δ 7.32-7.40 (m, 4H), 7.13-7.20 (m,
6H), 5.59-5.66 (m, 1H), 4.25 (d, J = 13.8 Hz, 1H), 3.41 (d,
J = 13.5 Hz, 2H), 3.20 (d, J = 13.2 Hz, 1H), 2.22 (s, 3H),
1.69 (d, J = 6.9 Hz, 3H); 13C NMR (75 MHz, CDCl3):
201.6, 172.1, 138.1, 136.2, 130.7, 130.2, 129.0, 128.0,
126.7, 125.6, 122.4, 121.0, 69.1, 51.1, 40.7, 27.0, 13.8; IR
(KBr): 3024.5, 2930.2, 1711.0, 1682.3, 1598.0, 1501.7,
1395.0, 912.5, 778.6 cm-1; HRMS (ESI) m/z: calcd. for
C21H21NO2 [M + Na]+: 342.1465, Found: 342.1458.
3-Acetyl-3-allyl-4-methylene-1-phenylpyrrolidin-2-one
(3la)
1
White solid (240.0 mg, 94%), m.p. 50-51 ºC; H NMR
(300 MHz, CDCl3): δ 7.68 (d, J = 7.8 Hz, 2H), 7.42 (t, J =
7.5 Hz, 2H), 7.22 (t, J = 7.5 Hz, 1H), 5.60-5.74 (m, 1H),
5.40 (t, J = 2.1 Hz, 1H), 5.12-5.19 (m, 2H), 5.05 (dd, J1 =
10.2 Hz, J2 = 1.8 Hz, 1H), 4.59 (dt, J1 = 14.1 Hz, J2 = 2.1
Hz, 1H), 4.44 (dt, J1 = 14.1 Hz, J2 = 2.4 Hz, 1H), 2.86-2.93
(m, 1H), 2.69-2.76 (m, 1H), 2.20 (s, 3H); 13C NMR (75
MHz, CDCl3): 201.1, 171.5, 138.9, 138.3, 132.0, 129.1,
125.5, 120.2, 119.8, 111.9, 68.0, 52.8, 38.8, 26.7; IR
(KBr): 2960.0, 2924.7, 1719.2, 1691.6, 1660.2, 1595.3,
1493.6, 1393.1, 918.7, 770.3 cm-1; HRMS (ESI) m/z: calcd.
for C16H17NO2 [M + Na]+: 278.1151, Found: 278.1152.
(Z)-3-acetyl-3-benzyl-4-benzylidene-1-
phenylpyrrolidin-2-one (3ac)
Yellow oil (312.8 mg, 82%); 1H NMR (300 MHz, CDCl3):
δ 7.31-7.40 (m, 7H), 7.15-7.22 (m, 8H), 6.50 (s, 1H), 4.45
(dd, J1 = 14.4 Hz, J2 = 2.1 Hz, 1H), 3.73 (dd, J1 = 14.4 Hz,
J2 = 2.4 Hz, 1H), 3.52 (d, J = 13.2 Hz, 1H), 3.36 (d, J =
12.9 Hz, 1H), 2.29 (s, 3H); 13C NMR (75 MHz, CDCl3):
201.4, 171.4, 137.8, 136.0, 135.4, 132.0, 130.2, 129.1,
128.9, 128.3, 128.1, 128.0, 127.0, 126.7, 125.9, 121.3, 70.1,
52.9, 41.3, 27.2; IR (KBr): 2993.9, 2874.3, 1713.4, 1687.5,
1660.7, 1497.3, 1450.8, 1402.5, 903.2, 750.8, 690.9 cm-1;
HRMS (ESI) m/z: calcd. for C26H23NO2 [M + Na]+:
404.1621, Found: 404.1623.
Ethyl 2-(3-acetyl-4-methylene-2-oxo-1-phenyl
pyrrolidin-3-yl)acetate (3ma)
1
White solid (286.3 mg, 95%), m.p. 57-58 ºC; H NMR
(300 MHz, CDCl3): δ 7.71 (d, J = 7.8 Hz, 2H), 7.43 (t, J =
7.5 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 5.35 (s, 1H), 5.16 (s,
1H), 4.61-4.72 (m, 2H), 4.06 (q, J = 7.2 Hz, 2H), 3.14-3.31
(m, 2H), 2.19 (s, 3H), 1.17 (t, J = 7.2 Hz, 3H); 13C NMR
(75 MHz, CDCl3): 199.5, 171.2, 170.5, 139.7, 138.5, 129.2,
125.5, 120.5, 111.2, 65.1, 60.8, 53.0, 38.5, 25.9, 14.1; IR
(KBr): 3079.4, 2987.4, 2930.0, 1732.0, 1696.0, 1599.5,
1503.7, 1403.7, 1196.9, 906.0, 767.1 cm-1; HRMS (ESI)
m/z: calcd. for C17H19NO4 [M + Na]+: 324.1206, Found:
324.1215.
General procedure for the synthesis of furans
4 (4pa as an example):
To a mixture of prop-2-ynylsulphonium salt 2a (271.6 mg,
1.5 mmol) and Cs2CO3 (488.7 mg, 1.5 mmol) in DMF (5.0
mL) was added 3-oxo-N-phenylbutanamide 1p (177.2 mg,
1.0 mmol). The resulting mixture was stirred at room
temperature for 0.5 h, which was then poured
into aqueous HCl solution (0.1 N, 50 mL) and extracted
with CH2Cl2 (3 × 20 mL). The combined organic phase
was washed with water (3 × 30 mL), dried over anhydrous
MgSO4, filtered, and evaporated in vacuo. The crude
product was purified by column chromatography (silica gel,
petroleum ether/ethyl acetate = 8:1) to give 4pa as a
reddish solid (183.0 mg, 85%).
3-Acetyl-4-methylene-1-phenyl-3-(prop-2-yn-1-
yl)pyrrolidin-2-one (3na)
1
White solid (233.0 mg, 92%), m.p. 105-106 ºC; H NMR
(300 MHz, CDCl3): δ 7.71 (d, J = 8.1 Hz, 2H), 7.44 (t, J =
8.1 Hz, 2H), 7.24 (t, J = 7.5 Hz, 1H), 5.46 (t, J = 2.4 Hz,
1H), 5.25 (t, J = 2.7 Hz, 1H), 4.65 (t, J = 2.4 Hz, 2H),
2.87-3.02 (m, 2H), 2.21 (s, 3H), 1.91 (t, J = 2.4 Hz, 1H);
13C NMR (75 MHz, CDCl3): 199.9, 170.7, 138.7, 138.2,
129.2, 129.1, 125.7, 120.5, 112.3, 79.4, 70.5, 67.1, 53.3,
26.5, 24.5; IR (KBr): 3264.3, 2996.4, 2924.9, 1714.8,
1690.3, 1662.2, 1599.2, 1503.3, 1399.2, 918.9, 760.9, 624
cm-1; HRMS (ESI) m/z: calcd. for C16H15NO2 [M + Na]+:
276.0995, Found: 276.0982.
Analytical data of furans 4
1-[4-Methyl-2-(phenylamino)furan-3-yl]ethanone (4pa)
1
Reddish solid (183.0 mg, 85%), m.p. 57-58 ºC; H NMR
(300 MHz, CDCl3): δ 10.51 (s, 1H), 7.30-7.40 (m, 4H),
7.05 (t, J = 7.2 Hz, 1H), 6.69 (d, J = 0.9 Hz, 1H), 2.40 (s,
3H), 2.20 (d, J = 1.2 Hz, 3H); 13C NMR (75 MHz, CDCl3):
192.8, 160.0, 138.0, 130.1, 129.3, 123.0, 118.6, 101.2, 28.7,
11.4; IR (KBr): 2961.4, 2927.8, 1723.7, 1637.7, 1601.2,
1567.5, 1501.7, 1226.8, 943.5, 753.8 cm-1; HRMS (ESI)
m/z: calcd. for C13H13NO2 [M + Na]+: 238.0838, Found:
238.0843.
2-(3-Acetyl-4-methylene-2-oxo-1-phenylpyrrolidin-3-
yl)acetonitrile (3oa)
Yellow oil (231.4 mg, 91%); 1H NMR (300 MHz, CDCl3):
δ 7.69 (d, J = 8.1 Hz, 2H), 7.45 (t, J = 7.8 Hz, 2H), 7.29 (d,
J = 7.5 Hz, 1H), 5.58 (s, 1H), 5.34 (s, 1H), 4.67-4.80 (m,
2H), 3.00-3.16 (m, 2H), 2.22 (s, 3H); 13C NMR (75 MHz,
CDCl3): 197.9, 168.8, 137.7, 136.9, 129.3, 126.3, 120.7,
1-[4-Methyl-2-(p-tolylamino)furan-3-yl]ethanone (4qa)
6
This article is protected by copyright. All rights reserved.

10.1002/adsc.201900693
Advanced Synthesis & Catalysis
1
1
White solid (190.3 mg, 83%), m.p. 67-68 ºC; H NMR
(300 MHz, CDCl3): δ 10.44 (s, 1H), 7.27 (d, J = 8.4 Hz,
2H), 7.13 (d, J = 8.4 HZ, 2H), 6.66 (d, J = 1.2 Hz, 1H),
2.39 (s, 3H), 2.19 (d, J = 1.2 Hz, 3H); 13C NMR (75 MHz,
CDCl3): 192.5, 160.3, 135.4, 132.7, 129.9, 129.8, 118.8,
118.6, 100.9, 28.6, 20.8, 11.4; IR (KBr): 3020.0, 2972.1,
2922.9, 1643.5, 1588.1, 1465.8, 1380.1, 1243.5, 946.4,
743.0 cm-1; HRMS (ESI) m/z: calcd. for C14H15NO2 [M +
Na]+: 252.0995, Found: 252.0998.
Yellow solid (232.9 mg, 84%), m.p. 53-54 ºC; H NMR
(300 MHz, CDCl3): δ 10.62 (s, 1H), 7.51-7.53 (m, 2H),
7.43-7.48 (m, 5H), 7.36 (t, J = 8.1 Hz, 2H), 7.09 (t, J = 7.2
Hz, 1H), 6.72 (d, J = 0.9 Hz, 1H), 1.62 (d, J = 0.9 Hz,
3H); 13C NMR (75 MHz, CDCl3): 191.4, 161.1, 141.3,
137.8, 130.8, 130.3, 129.4, 128.1, 127.3, 123.3, 118.8,
101.1, 11.0; IR (KBr): 3059.9, 2978.8, 2925.3, 1791.7,
1703.0, 1629.1, 1597.9, 1545.3, 1500.1, 1385.4, 945.0,
748.1 cm-1; HRMS (ESI) m/z: calcd. for C18H15NO2 [M +
Na]+: 300.0995, Found: 300.0993.
1-{2-[(4-Chlorophenyl)amino]-4-methylfuran-3-yl}
ethanone (4ra)
Methyl 4-methyl-2-(phenylamino)furan-3-carboxylate
(4wa)
1
White solid (215.3 mg, 88%), m.p. 124-125 ºC; H NMR
Yellow oil (154.9 mg, 67%); 1H NMR (300 MHz, DMSO‑
d6): δ 8.93 (s, 1H), 7.28-7.37 (m, 4H), 6.99-7.05 (m, 2H)
3.76 (s, 3H), 2.07 (s, 3H); 13C NMR (75 MHz, DMSO‑d6):
165.3, 158.4, 139.2, 131.1, 129.6, 122.8, 120.0, 118.8, 91.6,
51.2, 10.5; IR (KBr): 3067.7, 2928.8, 1714.3, 1637.5,
1600.4, 1567.2, 1500.8, 1397.8, 1256.7, 945.6, 751.3,
692.5 cm-1; HRMS (ESI) m/z: calcd. for C13H13NO3 [M +
Na]+:254.0788, Found: 254.0790.
(300 MHz, CDCl3): δ 10.51 (s, 1H), 7.28-7.33 (m, 4H),
6.70 (d, J = 0.9 Hz, 1H), 2.40 (s, 3H), 2.20 (d, J = 0.9 Hz,
3H); 13C NMR (75 MHz, CDCl3): 193.0, 159.5, 136.6,
130.3, 129.3, 127.8, 119.6, 118.7, 101.4, 28.8, 11.4; IR
(KBr): 2957.9, 2928.3, 1630.7, 1611.8, 1590.7, 1498.6,
1223.4, 946.8, 827.6, 720.3 cm-1; HRMS (ESI) m/z: calcd.
for C13H12ClNO2 [M + Na]+: 272.0449, Found: 272.0442.
1-{2-[(4-Methoxyphenyl)amino]-4-methylfuran-3-yl}
ethanone (4sa)
1-[2-(Butylamino)-4-methylfuran-3-yl)]thanone (4xa)
1
1
White solid (206.0 mg, 84%), m.p. 93-94 ºC; H NMR
Reddish solid (169.9 mg, 87%), m.p. 45-46 ºC; H NMR
(300 MHz, CDCl3): δ 10.37 (s, 1H), 7.30 (d, J = 9.0 Hz,
2H), 6.88 (d, J = 9.0 Hz, 2H), 6.63 (d, J = 0.9 Hz, 1H),
3.80 (s, 3H), 2.39 (s, 3H), 2.19 (d, J = 0.9 Hz, 3H); 13C
NMR (75 MHz, CDCl3): 192.3, 160.5, 155.8, 131.1, 129.7,
120.6, 118.6, 114.5, 100.6, 55.5, 28.6, 11.4; IR (KBr):
3131.0, 2963.4, 2936.5, 1726.9, 1635.4, 1567.4, 1511.2,
1230.4, 944.8, 731.2 cm-1; HRMS (ESI) m/z: calcd. for
C14H15NO3 [M + Na]+: 268.0944, Found: 268.0935.
(300 MHz, CDCl3): δ 8.19 (s, 1H), 6.49 (d, J = 0.9 Hz,
1H), 3.37 (q, J = 6.6 Hz, 2H), 2.30 (s, 3H), 2.12 (d, J = 0.9
Hz, 3H), 1.54-1.63 (m, 2H), 1.32-1.45 (m, 2H), 0.93 (t, J =
7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3): 191.2, 164.6,
129.0, 118.8, 99.1, 41.2, 32.2, 28.1, 19.9, 13.7, 11.5; IR
(KBr): 2960.3, 2932.9, 2873.6, 1641.8, 1565.9, 1455.1,
1397.4, 1078.3 cm-1; HRMS (ESI) m/z: calcd. for
C11H17NO2 [M + Na]+:218.1151, Found: 218.1143.
1-{4-Methyl-2-[(2-nitrophenyl)amino]furan-3-yl}
ethanone (4ta)
1-(2-(Benzylamino)-4-methylfuran-3-yl)ethanone (4ya)
1
White solid (194.9 mg, 85%), m.p. 93-94 ºC; H NMR
1
Yellow solid (213.4 mg, 82%), m.p. 125-126 ºC; H NMR
(300 MHz, CDCl3): δ 8.49 (s, 1H), 7.29-7.36 (m, 5H), 6.52
(s, 1H), 4.57 (d, J = 6.3 Hz, 2H), 2.32 (s, 3H), 2.14 (s, 3H);
13C NMR (75 MHz, CDCl3): 191.8, 164.2, 138.2, 129.4,
128.7, 127.5, 127.2, 118.9, 99.6, 45.4, 28.3, 11.4; IR (KBr):
2963.5, 2873.0, 1714.5, 1644.7, 1600.9, 1560.4, 1500.3,
1443.2, 1228.3, 940.7, 750.2 cm-1; HRMS (ESI) m/z: calcd.
for C14H15NO2 [M + Na]+:252.0995, Found: 252.0991.
(300 MHz, CDCl3): δ 10.72 (s, 1H), 8.36-8.37 (m, 1H),
7.88 (d, J = 7.5 Hz, 1H), 7.57 (d, J = 8.1 Hz, 1H), 7.47 (t,
J = 8.1 Hz, 2H), 6.81 (d, J = 0.9 Hz, 1H), 2.43 (s, 3H),
2.23 (d, J = 0.9 Hz, 3H); 13C NMR (75 MHz, CDCl3):
193.8, 158.6, 149.0, 139.2, 131.0, 130.0, 123.8, 118.7,
117.2, 112.4, 102.1, 28.9, 11.3; IR (KBr): 3037.9, 2967.0,
1633.4, 1610.6, 1531.6, 1397.9, 1342.7, 1231.5, 953.0,
724.5 cm-1; HRMS (ESI) m/z: calcd. for C13H12N2O4 [M +
Na]+: 283.0689, Found: 283.0686.
1-[4-Ethyl-2-(phenylamino)furan-3-yl]ethanone (4pb)
1
Yellow solid (181.1 mg, 79%), m.p. 43-44 ºC; H NMR
(300 MHz, CDCl3): δ 10.60 (s, 1H), 7.30-7.40 (m, 4H),
7.05 (t, J = 7.2 Hz, 1H), 6.66 (s, 1H), 2.64 (q, J = 7.2 Hz,
2H), 2.40 (s, 3H), 1.27 (t, J = 7.2 Hz, 3H); 13C NMR (75
MHz, CDCl3): 192.7, 160.2, 138.1, 129.4, 129.3, 125.5,
123.0, 118.6, 100.7, 28.8, 19.5, 13.0; IR (KBr): 2961.1,
2930.2, 2874.1, 1636.9, 1602.3, 1567.0, 1500.3, 1449.0,
944.0, 751.0 cm-1; HRMS (ESI) m/z: calcd. for C14H15NO2
[M + Na]+:252.0995, Found: 252.0991.
1-{2-[(2,4-Dimethylphenyl)amino]-4-methylfuran-3-yl}
ethanone (4ua)
1
White solid (209.2 mg, 86%), m.p. 150-151 ºC; H NMR
(300 MHz, CDCl3): δ 10.51 (s, 1H), 7.62 (d, J = 8.7 Hz
1H), 7.00-7.03 (m, 2H), 6.66 (s, 1H), 2.41 (s, 3H), 2.35 (s,
3H), 2.30 (s, 3H), 2.20 (s, 3H); 13C NMR (75 MHz,
CDCl3): 192.4, 160.7, 134.0, 132.8, 131.4, 130.0, 127.3,
126.9, 118.8, 118.6, 101.1, 28.5, 20.8, 18.0, 11.4 cm-1; IR
(KBr): 3015.0, 2953.0, 2862.0, 1714.2, 1643.5, 1598.0,
1497.2, 1449.7, 1219.0, 938.3, 727.4 cm-1; HRMS (ESI)
m/z: calcd. for C15H17NO2 [M + Na]+:266.1151, Found:
266.1146
1-(4-Benzyl-2-(phenylamino)furan-3-yl)ethanone (4pc)
1
Yellow solid (163.2 mg, 56%), m.p. 129-130 ºC; H NMR
(400 MHz, DMSO‑d6 ): δ 10.22 (s, 1H), 7.59-7.63 (m, 4H),
7.41 (t, J = 7.6 Hz, 2H), 7.30-7.34 (m, 3H), 7.13 (s, 1H),
7.06 (t, J = 7.2 Hz, 1H), 2.62 (dd, J1 = 10.8 Hz, J2 = 2.4 Hz,
1H), 2.53 (dd, J1 = 10.8 Hz, J2 = 2.4 Hz, 1H), 2.07 (s, 3H);
13C NMR (100 MHz, DMSO‑d6): 203.2, 165.2, 139.4,
136.3, 129.2, 129.1, 128.4, 127.7, 125.3, 123.9, 119.7,
[4-Methyl-2-(phenylamino)furan-3-yl](phenyl)
methanone (4va)
7
This article is protected by copyright. All rights reserved.

10.1002/adsc.201900693
Advanced Synthesis & Catalysis
119.1, 41.4, 25.7, 18.5; IR (KBr): 3039.2, 2931.2, 1703.4,
1641.2, 1601.3, 1565.0, 1500.8, 1448.2, 1224.1, 943.6,
752.3 cm-1; HRMS (ESI) m/z: calcd. for C19H17NO2 [M +
Na]+:314.1151, Found: 314.1153.
Testaferri, F. Marini, Tetrahedron Lett. 2013, 54,
6755-6757; g) A. L. Vergnon, R. S. Pottorf, M. P.
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910.
[5] a) S. Mao, L. Tang, C. Wu, X. Tu, Q. Gao, G. Deng,
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Acknowledgements
Financial support of this research by the National Natural
Science Foundation of China (21502185, 21542006 and
21850410454) and Department of Science and Technology of
Jilin Province, China (20170203005SF) is greatly acknowledged.
Dr. C. B. Rao thanks the award of CAS President's International
Fellowship for Postdoctoral Researchers (2018PM 0009).
[6] For selected reviews on sulfur ylides, see: a) Y. G.
Gololobov, V. P. Lysenko, I. E. Boldeskul,
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FULL PAPER
A Formal [3+2] Annulation of β-Oxoamides and 3-
Alkyl/arylprop-2-ynyl Sulfonium Salts: Substrate-
Controlled Chemoselective Synthesis of
Substituted γ-Lactams and Furans
Adv. Synth. Catal. Year, Volume, Page – Page
Bicheng Deng,a,b Chitturi Bhujanga Rao,b Rui
Zhang,b Jiacheng Li,b Yongjiu Liang,b Yanning
Zhao,*,a Ming Gao,a,b and Dewen Dong*, a,b
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