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Horsfiline:
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Kobayashi S., and Jørgensen K.A. (Eds), Wiley-VCH, Weinheim
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In: Kobayashi S., and Jørgensen K.A. (Eds). Cycloaddition Reactions in Organic Synthesis (2002), Wiley-VCH, Weinheim 187-209
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20
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0001696659
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Unique synthesis of spiro[indoline-3,2′-(1′,2′,3′,4′-tetrahydroquinoline)]-2,4′-diones derivatives has been reported, see:
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Unique synthesis of spiro[indoline-3,2′-(1′,2′,3′,4′-tetrahydroquinoline)]-2,4′-diones derivatives has been reported, see:. Al-Thebeiti M.S. Heterocycles 48 (1998) 145-150
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Al-Thebeiti, M.S.1
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50049111988
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note
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General experimental procedure for the synthesis of the ketimines: Isatin 7 (6.8 mmol) was dissolved in anhydrous methanol (50 mL) and the proper arylamines 8a-h were added (8.16 mmol) and then, the acid catalyst, AcOH (0.1-7.4 mL). The reaction mixture was refluxed, stirring constantly, for 3-8 h monitoring through TLC. After the reaction mixture reached room temperature, the precipitated solid was filtered and washed with petroleum ether, and then vacuum dried to get the ketimines 9a-h in good to excellent yields (50-86%).
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22
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50049090470
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note
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2: C, 71.42; H, 4.79; N, 11.10. Found: C, 71.23; H, 4.95; N, 11.05.
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23
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50049101606
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note
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General experimental procedure for the synthesis of the ketimine 9b in PEG 400: In a round-bottom flask, the isatin 7 (2.04 mmol) was dissolved in PEG 400 (5 mL) and the arylamine 8 b was added (2.44 mmol) stirring and heating at 80 °C for 3 h. The product formation is monitored by TLC comparing to the standard protocol of ketimine.
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24
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50049119819
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note
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4 and then concentrated by vacuum. The pure compounds 6a-h were obtained after recrystallization from heptanes/AcOEt (1/1) or silica gel column chromatography with petroleum ether and ethyl acetate as eluents (Table 1). It is important to note that trying to heat the reaction over the room temperature (25 °C) resulted in the ketimine rupture and the complete failure of the synthesis.
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25
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50049125473
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note
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3: C, 74.98; H, 6.04; N, 7.00. Found: C, 74.74; H, 6.23; N, 7.13.
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26
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50049128000
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note
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Indol)/64.1/132.1/141.5/177.7.
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27
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1642325021
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Indol was carried out). The similar case of the stereochemistry at the quaternary spiro and adjacent alkyl centers of spiro[pyrroline-3,3′-oxindoles] has been reported, see:
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Indol was carried out). The similar case of the stereochemistry at the quaternary spiro and adjacent alkyl centers of spiro[pyrroline-3,3′-oxindoles] has been reported, see:. Miyake F.Y., Yakushijin K., and Horne D.A. Org. Lett. 6 (2004) 711-713
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Miyake, F.Y.1
Yakushijin, K.2
Horne, D.A.3
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31
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50049111477
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note
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Their antifungal and cytotoxic properties are under way. These results will be published soon elsewhere.
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