July 2010
One-Pot Synthesis of New Spiro[cyclopropane-1,30-[3H]indol]-20(10H)-ones
from 3-Phenacylideneoxindoles
953
acetate and C¼¼O of oxindole overlapped), 1621, 1597 cmꢂ1
;
[6] Donaldson, W. A. Tetrahedron 2001, 57, 8589.
[7] Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem Rev
2003, 103, 1625.
1H NMR: d 2.09 (s, 3H, CH3), 2.21 (d, 1H, J ¼ 7 Hz, CH2a),
2.74 (d, 1H, J ¼ 7 Hz, CH2b), 6.99–7.98 (m, 8H, ArH), 8.48
(s, 1H, NH); Anal. Calcd. for C18H14BrNO3: C, 58.08; H,
3.79; N, 3.76. Found: C, 57.98; H, 3.73; N, 3.75%.
[8] Baba, Y.; Saha, G.; Nakao, S.; Iwata, C.; Tanaka, T.; Ibuka,
T.; Ohishi, H.; Takemoto, Y. J Org Chem 2001, 66, 81.
[9] Boger, D. L.; Hughes, T. V.; Hedrick, M. P. J Org Chem
2001, 66, 2207.
rel-(1R,2S)-2-Acetyloxy-2-(4-bromophenyl)spiro[cyclopro-
pane-1,30-[3H]indol]-20(10H)-one (3c). Light yellow solid
(1.15 g), yield 31%, decomp.>110ꢁC; IR (potassium bromide):
3419 (NAH), 3056, 3028, 2926, 2892, 1715 (broad, C¼¼O of
[10] Graham, D. W.; Ashton, W. T.; Barash, L.; Brown, J. E.;
Brown, R. D.; Canning, L. F.; Chen, A.; Springer, J. P.; Rogers, E. F.
J Med Chem 1987, 30, 1074.
acetate and C¼¼O of oxindole overlapped), 1620, 1597 cmꢂ1
;
[11] Salaun, J.; Baird, M. S. Curr Med Chem 1995, 2, 511.
[12] Yoshida, S.; Rosen, T. C.; Meyer, O. G. J.; Sloan, M. J.;
Ye, S.; Haufe, G.; Kirk, K. L. Bioorg Med Chem 2004, 12, 2645.
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[14] Yanovskaya, L. A.; Dombrovsky, V. A.; Khusid, A. Kh.
Tsiklopropanis funktsionalnimi gruppami. Sintez i primenenie; (Cyclo-
propanes with Functional Groups, Synthesis and Application), Nauka:
Moscow, 1980.
1H NMR: d 2.07 (s, 3H, CH3), 2.22 (d, 1H, J ¼ 7 Hz, CH2a),
2.55 (d, 1H, J ¼ 7 Hz, CH2b), 5.76 (d, 1H, J ¼ 8 Hz, H-40 of
oxindole), 6.73–7.87 (m, 7H, ArH), 8.39 (s, 1H, NH); Anal.
Calcd. for C18H14BrNO3: C, 58.08; H, 3.79; N, 3.76. Found:
C, 57.93; H, 3.65; N, 3.69%.
rel-(1R,2R)-2-Acetyloxy-2-(4-nitrophenyl)spiro[cyclopro-
pane-1,30-[3H]indol]-20(10)-one (2d). Light yellow solid (2.09
g), yield 62%, decomp.>154ꢁC; IR (potassium bromide): 3420
(NAH), 3080, 3031, 2925, 2890, 1719 (broad, C¼¼O of acetate
[15] Tsuji, T.; Nishida, S. The Chemistry of the Cyclopropyl
Group; Wiley: New York, NY, 1987.
1
and C¼¼O of oxindole overlapped), 1624, 1597 cmꢂ1; H NMR:
[16] Boche, G.; Walbirsky, H. M. Cyclopropane Derived Inter-
mediates; John Wiley: New York, NY, 1990.
d 2.09 (s, 3H, CH3), 2.24 (d, 1H, J ¼ 7 Hz, CH2a), 2.80 (d, 1H,
J ¼ 7 Hz, CH2b), 6.96–8.35 (m, 8H, ArH), 9.59 (s, 1H, NH);
13C NMR: d 21.13 (CH3), 26.87 (CH2), 38.23 (spiro carbon),
70.9 (NO2C6H4ACAOAc), 110.58, 122.56, 122.72, 123.60,
123.95, 126.52, 128.48, 131.23, 141.27, 141.70, 169.82
(ACOOA), 175.54 (ACONHA); Anal. Calcd. for C18H14N2O5:
C, 63.90; H, 4.17; N, 8.28. Found: C, 63.91; H, 4.11; N, 8.26%.
rel-(1R,2S)-2-Acetyloxy-2-(4-nitrophenyl)spiro[cyclopropane-
1,30-[3H]indol]-20(10H)-one (3d). Light yellow solid (0.94 g),
yield 28%, decomp.>154ꢁC; IR (potassium bromide): 3420
(NAH), 3082, 3031, 2924, 2890, 1719 (C¼¼O of acetate and
[17] Rappoport, Z. The Chemistry of the Cyclopropyl Group;
Wiley: New York, NY, 1996.
[18] Salau¨n, J. Topics In Current Chemistry; Small Ring Com-
pounds in Organic Synthesis VI: Cyclopropane Derivatives and their
Diverse Biological Activities, Vol. 207; Springer Berlin: Heidelberg,
2000; pp 1–67.
[19] Ellis, D.; Kuhen, K. L.; Anaclerio, B.; Wu, B.; Wolff, K.;
Yin, H.; Bursulaya, B.; Caldwell, J.; Karanewsky, D.; He, Y. Bioorg
Med Chem Lett 2006, 16, 4246.
[20] Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.;
White, A. H. Tetrahedron 2007, 63, 1191.
1
C¼¼O of oxindole overlapped), 1622, 1597 cmꢂ1; H NMR: d
[21] Ziyat, H.; Ait Itto, M. Y.; Ait Ali, M.; Riahi, A.; Karim,
A.; Daran, J.-C. Arkivoc 2006, xii, 152.
´
[22] Cruz, D. C.; Yuste, F.; Dıaz, E.; Ortiz, B.; Sanchez-Obre-
2.04 (s, 3H, CH3), 2.26 (d, 1H, J ¼ 7 Hz, CH2a), 2.59 (d, 1H,
J ¼ 7 Hz, CH2b), 5.8 (d, 1H, J ¼ 8 Hz, H-40 of oxindole),
6.66–8.65 (m, 7H, ArH), 9.49 (s, 1H, NH); 13C NMR: d 21.39
(CH3), 27.15 (CH2), 38.59 (spiro carbon), 71.11
(NO2C6H4ACAOAc), 110.22, 122.15, 122.76, 122.90, 123.77,
126.89, 128.25, 131.08, 141.16, 141.60, 170.87 (ACOOA),
175.94 (ACONHA); Anal. Calcd. for C18H14N2O5: C, 63.90;
H, 4.17; N, 8.28. Found: C, 63.78; H, 4.09; N, 8.20%.
´
gon, R.; Walls, F.; Ruano, J. L. G. Arkivoc 2005, vi, 211.
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Gorbunov, S. V.; Belyakov, P. A.; Nikishin, G. I. Tetrahedron Lett
2006, 47, 9129.
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eshchagin, A. N.; Nikishin, G. I. Tetrahedron 2008, 64, 708.
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dizadeh, M. R. Arkivoc 2006, xi, 47.
Acknowledgment. The authors sincerely appreciate for all fi-
nancial supports from the Research Vice-President of Islamic
Azad University (IAU), Saveh Branch.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet