4
Tetrahedron
R1
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OH
PhI(OAc)2
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N
N
10 min, 0 o
C
R2
3-5
1i
6i-8i
COOMe
COOEt
O
COOMe
O
MeOOC
EtOOC
O
N
N
N
7.
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8i, 65%
7i, 63%
6i, 83%
Scheme 2. DIB-Mediated reaction of 1-naphthaldehyde oxime 1i
with dipolarophiles 3–5.
Ph
Ph
O
I
OH
N
I
OAc
N
AcO
OAc
AcOH
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PhI
R1
R1
R2
O
N
[3+2]
cycloaddition
H
AcO
O
N
N
O
R2
AcOH
A
B
Scheme 3. Plausible mechanism for the formation of isoxazole
derivatives.
In summary, we have developed a rapid, simple and efficient
protocol for the synthesis of isoxazole derivative from easily
available starting materials under catalyst-free and mild reaction
conditions. The simplicity of experimental procedure and readily
availability of starting materials render this strategy as an
attractive method for the synthesis of isoxazole derivatives
bearing electron-deficient functionalities.
Acknowledgments
This work was supported by SERB (research grant No.
SR/S1/OC-38/2011) and DST-FIST program (HRMS facility),
New Delhi, and AS thanks MHRD and SKRP and AS thank
CSIR for research fellowships.
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