An efficient, one-pot, regioselective synthesis of 1,4-Diaryl-1 H -1,2,3-triazoles using click chemistry

Article abstract of DOI:10.1055/s-0029-1218765

An efficient, one-pot, regioselective synthesis of 1,4-diaryl-1H-1,2,3- triazoles is described via the copper(I)-catalyzed reaction of diaryliodonium salts, sodium azide and terminal alkynes. The generality of this protocol is demonstrated by the synthesis of a series of 1,4-diaryl-1H-1,2,3-triazoles in good to high yields. The catalyst and reaction solvent are reused without any appreciable reduction in product yield. Georg Thieme Verlag Stuttgart - New York.

Full text of DOI:10.1055/s-0029-1218765

PAPER
1687
An Efficient, One-Pot, Regioselective Synthesis of 1,4-Diaryl-1H-1,2,3-triazoles
Using Click Chemistry
R
egioselective Syn
a
thesis of 1,
l
4-Diar
i
yl-1
H
-1
p
,2,3-triazoles Kumar,* Vaddula Buchi Reddy
Chemistry Group, Birla Institute of Technology and Science, Pilani, Rajasthan-333 031, India
Fax +91(1596)244183; E-mail: dalipk@bits-pilani.ac.in
Received 4 January 2010; revised 12 February 2010
is sufficiently activated. Most of the existing protocols
Abstract: An efficient, one-pot, regioselective synthesis of 1,4-di-
aryl-1H-1,2,3-triazoles is described via the copper(I)-catalyzed re-
action of diaryliodonium salts, sodium azide and terminal alkynes.
The generality of this protocol is demonstrated by the synthesis of a
generally require long reaction times, a large excess of in-
organic azide, high boiling polar solvents (N,N-dimethyl-
formamide or dimethyl sulfoxide) and afford low to
series of 1,4-diaryl-1H-1,2,3-triazoles in good to high yields. The moderate yields of products. Previously, the synthesis of
catalyst and reaction solvent are reused without any appreciable re-
aryl azides was reported starting from aryl bromides/
iodides or aryl amines.13 Some of the protocols require
duction in product yield.
Key words: 1,4-diaryl-1H-1,2,3-triazoles, click chemistry, diaryl-
iodonium salts, aryl azides, cycloaddition
microwave irradiation or heating at reflux, the use of
freshly prepared reagents such as tert-butyl nitrite, or ex-
pensive reagents and ligands, and/or an inert atmosphere.
In addition, low molecular weight azides are dangerous
1,2,3-Triazoles have received significant attention due to because of their explosive nature.14 Thus, a simple and
their applications in fields such as materials, chemical and cost-effective method for the synthesis of 1,2,3-triazoles
biological sciences.1 These compounds are stable and tol- that avoids the isolation of intermediate aryl azides is
erate a variety of reaction conditions and functional highly desirable.
groups. They are also reported to possess diverse biologi-
We report herein a new and sequential one-pot synthesis
of 1,4-diaryl-1H-1,2,3-triazoles which involves in situ
generation of aryl azides via reaction of diaryliodonium
cal activity including anti-HIV,2 antiallergic,3 antifungal4
and antimicrobial5 action.
The preparation of 1,2,3-triazoles is typically accom- salts and sodium azide, followed by coupling with a ter-
plished via copper(I)-catalyzed 1,3-dipolar cycloaddition minal alkyne (Scheme 1).
between azides and alkynes.6 Alternative methods for
R
their synthesis include the reaction of nitriles and diazo
N
NaN3, CuI
+
R
compounds, cycloaddition between nitroethenes and tri-
methylsilyl azide in the presence of a catalyst, addition of
bromomagnesium acetylides to azides, and reactions of
sodium phenylacetylide and a sodium alkoxide with tosyl
or mesyl azides.7,8 Another report describes the synthesis
of 1,2,3-triazoles on a solid support.9 The copper(I)-cata-
lyzed azide–alkyne coupling reaction, the so-called
‘click’ reaction, was reported by Sharpless and co-work-
ers for the regioselective preparation of 1,4-disubstituted-
1,2,3-triazoles in high yields.10 As a result of its simplici-
ty, ability to tolerate various functional groups and the
ready availability of starting materials, click chemistry
has found wide application in organic synthesis, bioconju-
gation, materials science and drug discovery.11 Although,
click chemistry is applicable to various classes of chemi-
cal transformation, cycloaddition reactions of unsaturated
species predominate.
–
Ar2I
X
N
ArN3
N
r.t.
aq PEG 400
r.t.
Ar
1
2
Scheme 1 One-pot synthesis of 1,4-diaryl-1H-1,2,3-triazoles
During our initial efforts to prepare phenyl azide in situ,
the reaction of diphenyliodonium triflate with sodium
azide was attempted in water at different temperatures,
however, we did not obtain the desired product. In view of
our previously successful synthesis of 2-amino-2-
chromenes in aqueous polyethylene glycol 400 (PEG 400)
and the known advantages of this benign medium, we in-
stead explored the use of this polyether–water system as
solvent for this reaction.15 The best result for the in situ
generation of phenyl azide was obtained using copper(I)
iodide in PEG 400–water (1:1, v/v) solution at room tem-
perature. As a result of the weak nucleophilicity of the
counter anions and their high solubility, both diphenyl-
iodonium triflate and diphenyliodonium tosylate salts
were suitable and equally reactive starting materials for
the in situ generation of phenyl azide in good yield. Fol-
lowing successful conversion of diphenyliodonium tri-
flate into phenyl azide with copper(I) iodide in PEG 400–
water (1:1, v/v) solution, we next developed a new, se-
Aryl azides are very useful starting materials for the click
reaction and are generally prepared by treatment of dia-
zonium salts with azide ions.12 Nucleophilic displacement
by the azide ion can only be achieved if the aromatic ring
SYNTHESIS 2010, No. 10, pp 1687–1691
x
x.
x
x
.
2
0
1
0
Advanced online publication: 29.04.2010
DOI: 10.1055/s-0029-1218765; Art ID: P00110SS
© Georg Thieme Verlag Stuttgart · New York

1688
D. Kumar, V. B. Reddy
PAPER
quential, one-pot synthesis of 1,4-diaryl-1H-1,2,3-tria- nylacetylene in aqueous PEG 400, afforded pure 1,4-
zoles (Scheme 1). To our delight, the reaction of diphenyl-1H-1,2,3-triazole (2a) in 85% yield (Table 1).
diphenyliodonium triflate with sodium azide, followed by The structure of 2a was confirmed unambiguously by
a copper(I)-catalyzed 1,3-dipolar cycloaddition with phe- NMR spectroscopy and from mass spectral data. The 1H
Table 1 One-Pot Synthesis of 1,4-Diaryl-1H-1,2,3-triazoles 2
Iodonium salt
Alkyne
Product
Yield (%)a
85
–OTf
I+
N
N
N
N
1a
2a
N
–OTf
I+
N
1a
1a
2b
2c
79
75
N
N
–OTf
I+
N
F
F
–OTf
N
N
N
N
I+
1b
1b
2d
2e
82
76
N
–OTf
I+
N
N
N
–OTf
I+
N
1b
2f
71
F
F
–OTf
I+
N
N
N
N
N
1b
1c
2g
2h
77
85
N
–OTf
N
I+
N
–OTf
I+
N
N
N
1c
1c
2i
2j
N
81
78
–OTf
I+
N
N
F
F
F
N
N
–Br
I+
O2N
N
O2N
NO2
1d
2k
78
F
–OTs
I+
N
N
S
S
1e
1e
2l
74
71
S
S
S
N
–OTs
I+
N
N
2m
S
N
–OTs
I+
N
N
1f
2n
85
N
MeO
MeO
OMe
a Yield of isolated product.
Synthesis 2010, No. 10, 1687–1691 © Thieme Stuttgart · New York

PAPER
Regioselective Synthesis of 1,4-Diaryl-1H-1,2,3-triazoles
1689
at r.t. for a further 30 min. On completion of the reaction, as indicat-
ed by TLC, the product was extracted into Et2O (3 × 5 mL). The or-
ganic layer was dried over anhyd Na2SO4 and evaporated. The
residue was washed with hexane (5 mL) and the solid thus obtained
was recrystallized from EtOAc–Et2O to afford pure 1,4-diphenyl-
1H-1,2,3-triazole (2a).17 [CAUTION: Low-molecular-weight
azides are potentially explosive in nature and should be handled
with care.]
NMR spectrum of 2a exhibited a characteristic singlet at
d = 8.20 ppm due to the triazolyl C5-H proton. The high
resolution mass spectrum of this compound gave a molec-
ular ion peak at m/z = 221.0997 which was in agreement
with the calculated value.
The scope of this one-pot method was examined using di-
aryliodonium salts 1a–f and various terminal alkynes. In
addition to the triflate and tosylate salts, the use of bis(3-
nitrophenyl)iodonium bromide (1d) gave triazole 2k in
78% yield. The heteroaryl salt, bis(2-thienyl)iodonium to-
sylate (1e) yielded 1,4-diaryl-1H-1,2,3-triazoles 2l and
2m in 74% and 71% yields, respectively. Notably, the cy-
cloadditions of in situ generated aryl azides with terminal
alkynes were faster in aqueous PEG 400 solution (30 min-
utes) compared to those reported using tert-butanol–water
(12–24 hours).7a The competing formation of an N–H tri-
azole was observed when the three components were add-
ed simultaneously. The use of various diaryliodonium
salts and terminal alkynes demonstrates the functional
group tolerance of this three-component reaction
(Table 1). The products were isolated by extraction into
diethyl ether. Further, the recyclability of the solvent and
catalyst was demonstrated by successive syntheses (three
times) of 1,4-diphenyl-1H-1,2,3-triazole (2a), using re-
covered aqueous PEG 400, without any appreciable loss
in yield (first cycle: 85%; second cycle: 83%; third cycle:
78%).
Yield: 85%; mp 180–182 °C (Lit.17 mp 183–184 °C).
IR (KBr): 3121, 3053, 2918, 2853, 1599, 1504, 1229, 1042, 826,
758 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.20 (s, 1 H), 7.92 (d, J = 7.4 Hz,
2 H), 7.80 (d, J = 7.7 Hz, 2 H), 7.57–7.53 (m, 2 H), 7.48–7.45 (m, 3
H), 7.40–7.35 (m, 1 H).
13C NMR (100 MHz, CDCl3): d = 148.5, 137.2, 130.3, 129.9, 129.0,
128.9, 128.5, 125.9, 120.6, 117.7.
HRMS (ESI): m/z [M+] calcd for C14H11N3: 221.0953; found:
221.0997.
4-(4-Methylphenyl)-1-phenyl-1H-1,2,3-triazole (2b)
Yield: 79%; mp 166–169 °C.
IR (KBr): 2912, 2860, 1597, 1495, 1227, 1093, 1042, 814, 756
cm–1.
1H NMR (400 MHz, CDCl3): d = 8.15 (s, 1 H), 7.81–7.77 (m, 4 H),
7.55–7.52 (m, 2 H), 7.44 (t, J = 7.4 Hz, 1 H), 7.27–7.25 (m, 2 H),
2.39 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 148.5, 138.4, 137.2, 129.8, 129.7,
128.7, 127.5, 125.8, 120.6, 117.3, 21.4.
HRMS (ESI): m/z [M+] calcd for C15H13N3: 235.1109; found:
235.1396.
Mechanistically, the nucleophilic substitution reaction of
diaryliodonium salts with sodium azide proceeds via in
situ formation of aryl azides which then undergo 1,3-dipo-
lar cycloadditions with terminal alkynes to afford 1,4-di-
aryl-1H-1,2,3-triazoles 2. Symmetric diaryliodonium
salts (1a,b and 1d–f) gave the products by way of nucleo-
philic attack of the azide ion on either of the aryl rings,
whereas unsymmetrical diaryliodonium salt 1c underwent
attack on the more sterically demanding aromatic ring, in
line with earlier reported studies.16
4-(4-Fluoro-3-methylphenyl)-1-phenyl-1H-1,2,3-triazole (2c)
Yield: 75%; mp 144–147 °C.
IR (KBr): 3121, 2922, 2866, 1599, 1557, 1495, 1225, 1124, 1043,
816, 760, 689 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.14 (s, 1 H), 7.79–7.76 (m, 3 H),
7.68–7.65 (m, 1 H), 7.57–7.53 (m, 2 H), 7.46 (t, J = 7.4 Hz, 1 H),
7.08 (t, J = 9.0 Hz, 1 H), 2.34 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 161.5, 147.8, 137.1, 129.9, 129.1,
In conclusion, we have developed an efficient, safe, one- 128.9, 126.1, 125.6, 124.9, 120.6, 117.4, 115.6, 14.6.
HRMS (ESI): m/z [M + H]+ calcd for C15H13FN3: 254.1094; found:
254.1090.
pot, regioselective synthesis of 1,4-diaryl-1H-1,2,3-tri-
azoles in good yields, under catalytic conditions, using
various diaryliodonium salts and terminal alkynes. The re-
cyclability of the aqueous PEG 400 solvent along with the
catalyst is a noteworthy feature of this protocol.
1-(4-Methylphenyl)-4-phenyl-1H-1,2,3-triazole (2d)
Yield: 82%; mp 166–168 °C.
IR (KBr): 3125, 2914, 2860, 1520, 1481, 1229, 1045, 816, 692
cm–1.
Melting points were obtained using an EZ-Melt MPA 120 melting
point apparatus and are uncorrected. 1H NMR and 13C NMR spectra
were recorded on a Bruker Avance II 400 NMR spectrometer using
TMS as the internal standard. Chemical shifts are given in parts per
million (d) and coupling constants (J) in Hz. HRMS data were ob-
tained using electrospray ionization on a Quadrupole–Time-of-
flight (Q-Tof II) mass spectrometer (Micromass, Manchester, UK).
Thin-layer chromatography (TLC) was performed on Merck silica
gel 60 F254 precoated aluminum sheets.
1H NMR (400 MHz, CDCl3): d = 8.15 (s, 1 H), 7.92–7.90 (m, 2 H),
7.66 (d, J = 8.4 Hz, 2 H), 7.47–7.44 (m, 2 H), 7.38–7.32 (m, 3 H),
2.43 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 148.3, 139.0, 134.9, 130.4, 130.3,
129.0, 128.4, 125.9, 120.5, 117.7, 21.2.
HRMS (ESI): m/z [M+] calcd for C15H13N3: 235.1109; found:
235.1525.
1,4-Bis(4-methylphenyl)-1H-1,2,3-triazole (2e)
Yield: 76%; mp 196–199 °C.
1,4-Diphenyl-1H-1,2,3-triazole (2a); Typical Procedure
A mixture of diphenyliodonium triflate (1a) (430 mg, 1.0 mmol),
NaN3 (65 mg, 1.0 mmol) and CuI (19 mg, 10 mol%) in PEG 400–
H2O (1 mL, 1:1, v/v) was stirred at r.t. for 30 min. Phenylacetylene
(102 mg, 1.0 mmol) was added and the reaction mixture was stirred
IR (KBr): 3105, 3022, 2916, 2860, 1520, 1497, 1229, 1022, 814
cm–1.
Synthesis 2010, No. 10, 1687–1691 © Thieme Stuttgart · New York

1690
D. Kumar, V. B. Reddy
PAPER
1H NMR (400 MHz, CDCl3): d = 8.10 (s, 1 H), 7.79 (d, J = 8.1 Hz,
2 H), 7.65 (d, J = 8.4 Hz, 2 H), 7.32 (d, J = 8.2 Hz, 2 H), 7.26 (d,
J = 7.9 Hz, 2 H), 2.42 (s, 3 H), 2.39 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 148.4, 138.9, 138.3, 134.9, 130.3,
129.6, 127.6, 125.8, 120.5, 117.3, 21.4, 21.2.
IR (KBr): 2922, 2854, 1603, 1487, 1227, 1049, 824 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.79 (dd, J = 7.3, 1.6 Hz, 1 H),
7.77 (s, 1 H), 7.69–7.65 (m, 1 H), 7.08 (t, J = 9.0 Hz, 1 H), 7.01 (s,
2 H), 2.36 (s, 3 H), 2.35 (s, 3 H), 2.01 (s, 6 H).
13C NMR (100 MHz, CDCl3): d = 161.4, 147.0, 140.2, 135.2, 133.5,
129.2, 129.0, 126.4, 125.5, 124.8, 121.2, 115.6, 21.2, 17.4, 14.7.
HRMS (ESI): m/z [M + H]+ calcd for C16H16N3: 250.1344; found:
250.1346.
HRMS (ESI): m/z [M+] calcd for C18H18FN3: 295.1485; found:
295.1831.
4-(4-Fluoro-3-methylphenyl)-1-(4-methylphenyl)-1H-1,2,3-tri-
azole (2f)
Yield: 71%; mp 168–171 °C.
4-(4-Fluoro-3-methylphenyl)-1-(3-nitrophenyl)-1H-1,2,3-tri-
azole (2k)
IR (KBr): 3123, 2951, 2924, 2864, 1557, 1520, 1495, 1223, 1124,
1043, 816 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.09 (s, 1 H), 7.76 (dd, J = 7.4, 1.6
Hz, 1 H), 7.67–7.64 (m, 3 H), 7.33 (d, J = 8.2 Hz, 2 H), 7.07 (t,
J = 8.9 Hz, 1 H), 2.43 (s, 3 H), 2.34 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 161.4, 147.7, 139.0, 134.8, 130.3,
129.1, 126.2, 125.5, 124.9, 120.5, 117.4, 115.5, 21.2, 14.7.
Yield: 78%; mp 175–177 °C.
IR (KBr): 3098, 1611, 1537, 1504, 1348, 1232, 1045, 804 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.04 (s, 1 H), 7.70–7.65 (m, 3 H),
7.60–7.56 (m, 1 H), 7.47–7.43 (m, 2 H), 7.01 (t, J = 8.9 Hz, 1 H),
2.27 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 161.6, 148.1, 135.9, 134.7, 130.1,
129.2, 129.1, 125.9, 125.8, 125.6, 124.9, 121.7, 117.2, 115.6, 14.7.
HRMS (ESI): m/z [M + H]+ calcd for C15H12FN4O2: 299.0944;
found: 299.0943.
HRMS (ESI): m/z [M + H]+ calcd for C16H14FN3: 268.1250; found:
268.1245.
2-[1-(4-Methylphenyl)-1H-1,2,3-triazol-4-yl]pyridine (2g)
Yield: 77%; mp 128–129 °C.
4-Phenyl-1-(2-thienyl)-1H-1,2,3-triazole (2l)
Yield: 74%; mp 136–139 °C.
IR (KBr): 3107, 3025, 2920, 1595, 1520, 1232, 1036, 989, 814
cm–1.
1H NMR (400 MHz, CDCl3): d = 8.63–8.61 (m, 1 H), 8.57 (s, 1 H),
8.27–8.24 (m, 1 H), 7.84–7.79 (m, 1 H), 7.70–7.67 (m, 2 H), 7.34
(d, J = 8.6 Hz, 2 H), 7.28–7.25 (m, 1 H), 2.43 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 150.1, 149.5, 148.8, 139.0, 137.0,
134.7, 130.3, 123.1, 120.5, 120.4, 120.0, 21.1.
IR (KBr): 3098, 2922, 2851, 1556, 1485, 1230, 1034, 822, 763
cm–1.
1H NMR (400 MHz, CDCl3): d = 8.10 (s, 1 H), 7.89 (d, J = 4.0 Hz,
2 H), 7.46 (t, J = 7.2 Hz, 2 H), 7.39–7.35 (m, 1 H), 7.29 (dd, J = 3.6,
1.2 Hz, 1 H), 7.24 (dd, J = 5.2, 1.2 Hz, 1 H), 7.07–7.04 (m, 1 H).
13C NMR (100 MHz, CDCl3): d = 148.4, 138.6, 129.9, 128.9, 128.6,
126.3, 125.9, 122.9, 118.9, 118.2.
HRMS (ESI): m/z [M + H]+ calcd for C14H13N4: 237.1140; found:
237.1142.
HRMS (ESI): m/z [M + H]+ calcd for C12H10N3S: 228.0595; found:
228.0604.
1-Mesityl-4-phenyl-1H-1,2,3-triazole (2h)
Yield: 85%; mp 113–116 °C.
4-(4-Methylphenyl)-1-(2-thienyl)-1H-1,2,3-triazole (2m)
Yield: 71%; mp 167–170 °C.
IR (KBr): 3136, 2916, 2860, 1607, 1495, 1223, 1034, 856, 768
cm–1.
1H NMR (400 MHz, CDCl3): d = 7.94–7.92 (m, 2 H), 7.83 (s, 1 H),
7.48–7.44 (m, 2 H), 7.38–7.34 (m, 1 H), 7.01 (s, 2 H), 2.37 (s, 3 H),
2.02 (s, 6 H).
13C NMR (100 MHz, CDCl3): d = 147.6, 140.2, 135.2, 133.6, 130.6,
129.1, 129.0, 128.3, 125.8, 121.5, 21.2, 17.4.
IR (KBr): 3109, 2914, 2857, 1558, 1495, 1466, 1221, 1038, 818,
710 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.06 (s, 1 H), 7.77 (d, J = 8.1 Hz,
2 H), 7.28–7.25 (m, 3 H), 7.23–7.21 (m, 1 H), 7.05–7.03 (m, 1 H),
2.39 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 148.4, 138.6, 138.5, 129.6, 127.0,
126.3, 125.8, 122.8, 118.5, 118.1, 21.4.
HRMS (ESI): m/z [M + H]+ calcd for C17H17N3: 264.1501; found:
264.1800.
HRMS (ESI): m/z [M + H]+ calcd for C13H12N3S: 242.0752; found:
242.0758.
1-Mesityl-4-(4-methylphenyl)-1H-1,2,3-triazole (2i)
Yield: 81%; mp 125–128 °C.
IR (KBr): 2920, 2859, 1607, 1487, 1224, 1038, 856, 806 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.81 (d, J = 8.1 Hz, 2 H), 7.79 (s,
1 H), 7.27 (d, J = 7.9 Hz, 2 H), 7.00 (s, 2 H), 2.40 (s, 3 H), 2.36 (s,
3 H), 2.01 (s, 6 H).
13C NMR (100 MHz, CDCl3): d = 147.7, 140.1, 138.2, 135.2, 133.6,
129.6, 129.1, 127.7, 125.7, 121.2, 21.4, 21.2, 17.4.
1-(4-Methoxyphenyl)-4-phenyl-1H-1,2,3-triazole (2n)17
Yield: 85%; mp 164–165 °C (Lit.17mp 160–161 °C).
IR (KBr): 3126, 2841, 1611, 1518, 1252, 1030, 829, 768 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.11 (s, 1 H), 7.92–7.89 (m, 2 H),
7.69 (d, J = 9.0 Hz, 2 H), 7.47–7.43 (m, 2 H), 7.38–7.34 (m, 1 H),
7.04 (d, J = 9.0 Hz, 2 H), 3.88 (s, 3 H).
Acknowledgment
HRMS (ESI): m/z [M + H]+ calcd for C18H20N3: 278.1657; found:
278.1654.
We thank DRDO, New Delhi and Birla Institute of Technology and
Science, Pilani for financial support and SAIF, Panjab University,
Chandigarh for providing spectral data.
4-(4-Fluoro-3-methylphenyl)-1-mesityl-1H-1,2,3-triazole (2j)
Yield: 78%; mp 112–115 °C.
Synthesis 2010, No. 10, 1687–1691 © Thieme Stuttgart · New York

PAPER
Regioselective Synthesis of 1,4-Diaryl-1H-1,2,3-triazoles
1691
(10) (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless,
K. B. Angew. Chem. Int. Ed. 2002, 41, 2596. (b) Himo, F.;
Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.;
Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127,
210.
(11) For reviews, see: (a) Kolb, H. C.; Finn, M. G.; Sharpless, K.
B. Angew. Chem. Int. Ed. 2001, 40, 2004. (b) Kolb, H. C.;
Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.
(c) Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007,
36, 1249. (d) Gil, M. V.; Arevalo, M. J.; Lopez, O. Synthesis
2007, 1589.
(12) (a) Liu, Q.; Tor, Y. Org. Lett. 2003, 5, 2571. (b) Zhu, W.;
Ma, D. Chem. Commun. 2004, 888.
(13) (a) Barral, K.; Moorhouse, A. D.; Moses, J. E. Org. Lett.
2007, 9, 1809. (b) Anderson, J.; Bolvig, S.; Liang, X. Synlett
2005, 2941. (c) Anderson, J.; Madsen, U.; Bjorkling, F.;
Liang, X. Synlett 2005, 2209.
References
(1) (a) Krasiski, A.; Radi, Z.; Manetsch, R.; Raushel, J.; Taylor,
P.; Sharpless, K. B.; Kolb, H. C. J. Am. Chem. Soc. 2005,
127, 6686. (b) Suijkerbuijk, B. M. J. M.; Aerts, B. N. H.;
Dijkstra, H. P.; Lutz, M.; Spek, A. L.; Koten, G. V.;
Gebbink, R. J. M. K. Dalton Trans. 2007, 1273. (c) Binder,
W. H.; Kluger, C. Curr. Org. Chem. 2006, 10, 1791.
(2) Alvarez, R.; Velazquez, S.; San Felix, A.; Aquaro, S.;
De Clercq, E.; Perno, C.-F.; Karlsson, A.; Balzarini, J.;
Camarasa, M. J. J. Med. Chem. 1994, 37, 4185.
(3) Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A.
J. Med. Chem. 1986, 29, 2262.
(4) (a) Vicentini, C. B.; Brandolini, V.; Guarneri, M.; Giori, P.
Farmaco 1992, 47, 1021. (b) Fung-Tomc, J. C.; Huczko, E.;
Minassian, B.; Bonner, D. P. Antimicrob. Agents
Chemother. 1998, 42, 313.
(5) Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn,
M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega,
K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer,
R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R.
D.; Stapert, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953.
(6) (a) Odlo, K.; Hoydahl, E. A.; Hansen, T. V. Tetrahedron
Lett. 2007, 48, 2097. (b) Smith, C. D.; Baxendale, I. R.;
Lanners, S.; Hayward, J. J.; Smith, S. C.; Ley, S. V. Org.
Biomol. Chem. 2007, 5, 1559. (c) Basak, A.; Chandra, K.;
Pal, R.; Ghosh, S. C. Synlett 2007, 1585. (d) Chen, H.;
Taylor, J. L.; Abrams, S. R. Bioorg. Med. Chem. Lett. 2007,
17, 1979.
(7) (a) Yang, D.; Fu, N.; Liu, Z.; Li, Y.; Chen, B. Synlett 2007,
278. (b) Evans, W. J.; Montalvo, E.; Champagne, T. M.;
Ziller, J. W.; DiPasquale, A. G.; Rheingold, A. L. J. Am.
Chem. Soc. 2008, 130, 16. (c) Amantini, D.; Fringuelli, F.;
Piermatti, O.; Pizzo, F.; Zunino, E.; Vaccaro, L. J. Org.
Chem. 2005, 70, 6526.
(14) (a) Agrawal, J. P.; Hodgson, R. D. Organic Chemistry of
Explosives; John Wiley & Sons Ltd: Chichester, 2007.
(b) Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew.
Chem. Int. Ed. 2005, 44, 5188.
(15) (a) Kumar, D.; Reddy, V. B.; Mishra, B. G.; Rana, R. K.;
Mallikarjuna, N. N.; Varma, R. S. Tetrahedron 2007, 63,
3093. (b) Cho, E.; Gwak, H.; Chun, I. Int. J. Pharm. 2008,
349, 101. (c) Ishida, T.; Wang, X.-Y.; Shimizu, T.; Nawata,
K.; Kiwada, H. J. Controlled Release 2007, 122, 349.
(d) Yu, P.; Zheng, C.; Chen, J.; Zhang, G.; Liu, Y.; Suo, X.;
Zhang, G.; Su, Z. Bioorg. Med. Chem. 2007, 15, 5396.
(e) Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D.
Green Chem. 2005, 7, 64.
(16) (a) Lubinkowski, J. J.; Arrieche, C. G.; McEwen, W. E.
J. Org. Chem. 1980, 45, 2076. (b) Lubinkowski, J. J.;
Knapczyk, J. W.; Calderon, J. L.; Petit, L. R.; McEwen, W.
E. J. Org. Chem. 1975, 40, 3010. (c) Lubinkowski, J. J.;
Gomez, M.; Calderon, J. L.; McEwen, W. E. J. Org. Chem.
1978, 43, 2432. (d) Carroll, M. A.; Wood, R. A.
Tetrahedron 2007, 63, 11349; and references cited therein.
(17) Campbell-Verduyn, L. S.; Mirfeizi, L.; Dierckx, R. A.;
Elsinga, P. H.; Feringa, B. L. Chem. Commun. 2009, 2139.
(8) (a) Krasinski, A.; Fokin, V. V.; Sharpless, K. B. Org. Lett.
2004, 6, 1237. (b) Boyer, J.; Mack, C.; Goebel, N.; Morgan,
L. J. Org. Chem. 1958, 23, 1051.
(9) Gao, Y.; Lam, Y. Org. Lett. 2006, 8, 3283.
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