880 Bull. Chem. Soc. Jpn., 74, No. 5 (2001)
Spiro[oxindole-3,2′-[1,3,4]oxadiazolines]
three crystals are deposited as Document No. 74034 at the Office
of the Editor of Bull. Chem. Soc. Jpn. Crystallographic data have
been deposited at the CCDC, 12 Union Road, Cambridge CB2
1EZ, UK and copies can be obtained on request, free of charge, by
quoting the publication citation and the deposition numbers
CCDC 157190.
References
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1
General Operations of Processing the Reaction Mixtures.
(see Tables 1 and 2). (A) The product was filtered off in the cold.
(B) The reaction mixture was cooled and poured into ice and wa-
ter. (C) The reaction mixture was concentrated. (D) The cold res-
idue was triturated with a small amount of anhydrous EtOH and
kept at room temperature for 0.5 h; then hexane was added. (E)
Water was added to the hot reaction mixture. (F) The mixture was
cooled and water was added. (G) The cold residue was triturated
with water. (H) The cold residue was triturated with EtOH, kept at
room temperature for ꢀ0.5 h and then concentrated and triturated
with Et2O; to the crystalline material hexane was added. (I) The
filtrate was concentrated. (J) Trituration of the cold residue with
2-PrOH and subsequent addition of hexane afforded a crude prod-
uct. (K) A solution of the product in CHCl3 was treated with char-
coal and then concentrated. The residue was crystallized from the
solvent indicated in the Table.
2
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′
′
2-Acetoxy-N,N ,N -triacetyl-benzohydrazide (4c).
A mix-
ture of the salicylohydrazide 4a (1.5215 g, 10 mmol), anhydrous
NaOAc (1.500 g, ꢀ18.3 mmol), and Ac2O (15 ml, 159 mmol) was
stirred at 103 ˚C (bath) until dissolution was complete (ꢀ10 min)
and for an additional 30 min, and then concentrated. The residue
was treated with ice/water and extracted with CHCl3, the organic
layer was washed with aq NaHCO3 and water, dried (MgSO4), and
concentrated. Purification of the residue by column chromatogra-
phy [silica gel 60, CHCl3/EtOAc (98:2)] afforded the pure prod-
uct (4c, 1.730 g, 54%), mp 65 ˚C (from EtOAc with additon of
3
B. Lenkey and L. Somogyi, Acta Microbiol. Immunol.
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4
L. Somogyi, Liebigs Ann. Chem., 1993, 931, and referenc-
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5
a) K. H. Mayer and D. Lauerer, Liebigs Ann. Chem., 731,
1
hexane) (Chart 4) 360 MHz H NMR (CDCl3): δ 7.58–7.52 (m,
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2H) and 7.32–7.22 (m, 2H) (4 aromatic H), 2.38 (s, 6H), 2.35 (s,
3H), and 2.29 (s, 3H) (all the 3 signals are split by 1.4 Hz, presum-
ably due to a hindered rotation, 4 Ac). IR (KBr) 1746 (s), 1736
(s), 1714 (s), 1688 (s), 1606 cmꢁ1 (m). Found: C, 56.32; H, 4.95;
N, 8.75%. Calcd for C15H16N2O6: C, 56.24; H, 5.04; N, 8.75%.
6
V, N. Yandovskii and I. A. Zamorina, Zh. Org. Khim., 12,
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L. Somogyi, Tetrahedron, 41, 5187 (1985), and references
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R2
R3
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8
9
L. Somogyi, Liebigs Ann. Chem., 1991, 1267.
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4a
b
H
Ac
H
H
H
Ac
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c
Ac Ac Ac
Chart 4.
The author is indebted to Attila Cs. Bényei, Ph.D. [(Labora-
tory for X-ray Diffraction, Department of Chemistry, Universi-
ty of Debrecen, H-4010 Debrecen, P.O. Box 7) for the X-ray
diffraction investigations supported by Tempus JEP (Grant No.
9252-95) and the Hungarian Scientific Research Fund (OTKA
Grant No. D25136 and M28249)], and greatly obliged to the
Hungarian Scientific Research Fund (for grant OTKA
T025016).
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