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Volumn 49, Issue 41, 2008, Pages 5855-5857

A simple entry to novel spiro dihydroquinoline-oxindoles using Povarov reaction between 3-N-aryliminoisatins and isoeugenol

Author keywords

Dihydrospiro indoline 3,2 quinoline 2 ones; Imino Diels Alder cycloaddition; Isatin; Isoeugenol

Indexed keywords

4' (4 HYDROXY 3 METHOXYPHENYL) 3' METHYL 3',4' DIHYDRO 1'H SPIRO(INDOLINE 3,2' QUINOLIN) 2 ONE; EUGENOL; INDOLE DERIVATIVE; OXINDOLE; QUINOLINE DERIVATIVE; SPIRO DIHYDROQUINOLINE OXINDOLE; UNCLASSIFIED DRUG;

EID: 50049108112     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.096     Document Type: Article
Times cited : (53)

References (31)
  • 19
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    • Kobayashi S., and Jørgensen K.A. (Eds), Wiley-VCH, Weinheim
    • In: Kobayashi S., and Jørgensen K.A. (Eds). Cycloaddition Reactions in Organic Synthesis (2002), Wiley-VCH, Weinheim 187-209
    • (2002) Cycloaddition Reactions in Organic Synthesis , pp. 187-209
  • 20
    • 0001696659 scopus 로고    scopus 로고
    • Unique synthesis of spiro[indoline-3,2′-(1′,2′,3′,4′-tetrahydroquinoline)]-2,4′-diones derivatives has been reported, see:
    • 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
    • (1998) Heterocycles , vol.48 , pp. 145-150
    • Al-Thebeiti, M.S.1
  • 21
    • 50049111988 scopus 로고    scopus 로고
    • note
    • 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%).
  • 22
    • 50049090470 scopus 로고    scopus 로고
    • note
    • 2: C, 71.42; H, 4.79; N, 11.10. Found: C, 71.23; H, 4.95; N, 11.05.
  • 23
    • 50049101606 scopus 로고    scopus 로고
    • note
    • 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.
  • 24
    • 50049119819 scopus 로고    scopus 로고
    • note
    • 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.
  • 25
    • 50049125473 scopus 로고    scopus 로고
    • note
    • 3: C, 74.98; H, 6.04; N, 7.00. Found: C, 74.74; H, 6.23; N, 7.13.
  • 26
    • 50049128000 scopus 로고    scopus 로고
    • note
    • Indol)/64.1/132.1/141.5/177.7.
  • 27
    • 1642325021 scopus 로고    scopus 로고
    • 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:
    • 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
    • (2004) Org. Lett. , vol.6 , pp. 711-713
    • Miyake, F.Y.1    Yakushijin, K.2    Horne, D.A.3
  • 31
    • 50049111477 scopus 로고    scopus 로고
    • note
    • Their antifungal and cytotoxic properties are under way. These results will be published soon elsewhere.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.