Org aP nl ei ca s &e dB oi on mo to al ed cj uu sl at rm Ca hr ge imn si stry
Page 6 of 7
ARTICLE
Journal Name
Ethyl 6‐bromo‐5'‐(diethoxyphosphoryl)‐2‐oxospiro[indoline‐3,3'‐
and M. K. Brennan, Org. Lett., 2006, 8, 2027; h) M. P. Castaldi,
pyrazole]‐4'‐carboxylate (3n)
Yield: 84%; White solid; mp: 168‐170 °C; H NMR (200 MHz, CDCl
DOI: 10.1039/C5OB01020A
D. M. Troast, J. A. Porco, Jr., Org. Lett., 2009, 11, 3362; i) P. B.
Alper, C. Meyers, A. Lerchner, D. R. Siegel and E. M. Carreira,
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1
3
)
δ: 1.36‐1.54 (m, 9H), 4.25‐4.57 (m, 6H), 7.41‐7.74 (m, 2H), 8.99 (d, J
1
3
=
8.0 Hz, 1H), 10.5 (br s, 1H); C NMR (50 MHz, CDCl
3
) δ: 13.6, 15.9
2
2
, 4083; k) L. E. Overman and D. A. Watson, J. Org. Chem.,
006, 71, 2587; l) S. T. Hilton, T. C. T. Ho, G. Pljevaljcic and K.
(d, JC–P = 6.3 Hz), 16.0 (d, JC–P = 6.3 Hz), 61.7, 63.4 (d, JC–P = 5.3 Hz),
6
1
1
6
4
3.5 (d, JC–P = 5.3 Hz), 112.2, 112.3, 112.5, 114.1 (d, JC–P = 22.5 Hz),
14.3 (d, JC–P = 22.5 Hz), 117.9, 119.5, 119.7, 131.3, 141.0, 143.6,
Jones, Org. Lett., 2000, 2, 2639; m) Z. Mao and S. W. Baldwin,
Org. Lett. 2004, 6, 2425; n) K. S. Feldman and A. G. Karatjas,
Org. Lett. 2006, 8, 4137.
S. C. Fields, Tetrahedron 1999, 55, 12237.
P. Balczewski and A. Bodzioch, Organophosphorus Chem., 2009,
3
1
46.2, 148.4, 156.8, 159.3, 161.9; P NMR (202.4 MHz, CDCl ) δ:
3
3
4
+
.26; HRMS (ESI) calcd for C17
72.0266.
H
20
N
3
O
6
BrP [M+H] 472.0268; found
3
8, 279.
5
6
For an example, see: C. Belmant, E. Espinosa, R. Poupot, M. A
Peyrat, M. Guiraud, Y. Poquet, M. Bonneville and J. J. Fournie, J.
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Conclusion
In summary, we have developed a simple one pot highly
efficient and completely regioselective synthesis of 3,3’‐spiro‐
phosphonylpyrazole‐oxindoles in good yields via base
mediated 1,3‐dipolar cycloaddition reaction between
methyleneindolinones and Bestmann‐Ohira reagent. Attractive
features of this process are 1) its versatility, mild reaction
condition, short reaction time, high yield and the efficiency in
creating a complex core in a single operation. 2) Provides an
efficient access to series of biologically important 3,3’‐spiro‐
phosphonylpyrazole‐oxindole in good yield with excellent
regioselectivity. The scope of the reaction was expanded with
the development of multicomponent reaction sequence in
single step. This methodology is fascinating because it provides
a quick and easy access to libraries of molecules of
pharmaceutical interests under mild reaction condition.
1
93.
7
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4
Acknowledgments
1
996, Vol. 3, p 1. For selected recent reviews, see: (b) A. V.
We sincerely thank UGC, New Delhi, India for the award of a
senior research fellowship. The authors are also thankful to Dr.
V. V. Ranade, Chair, Chemical Engineering and Process
Development Division for his constant encouragement and
support. We thank Dr. Rajesh G. Gonnade and Ms. Ekta
Sangtani (Center for Materials Characterization, CSIR‐NCL) for
assistance with X‐ray crystallography.
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