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Volumn , Issue 6, 2007, Pages 874-880

Solid-supported microwave-accelerated intramolecular knoevenagel hetero-Diels-Alder reactions: A protocol for the synthesis of Indolo[2,1-a]pyrrolo[4′,3′:4,5]pyran ring systems

Author keywords

Domino process; Hetero Diels Alder; Indole; Knoevenagel condensation

Indexed keywords

INDOLE DERIVATIVE; INDOLO[2,1 ALPHA]PYRROLO[4',3':4,5]PYRAN; PYRROLOINDOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34247226059     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-970788     Document Type: Article
Times cited : (21)

References (19)
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    • (1985) The Alkaloids , vol.26
    • Husson, H.-P.1
  • 3
    • 0006644371 scopus 로고
    • Herz, W, Griesbach, H, Kirby, G. W, Tamm, C, Eds, Springer-Verlag: Wien
    • Franck, R. W. In Progress in the Chemistry of Organic Natural Products, Vol. 50; Herz, W.; Griesbach, H.; Kirby, G. W.; Tamm, C., Eds.; Springer-Verlag: Wien, 1986, 27-56.
    • (1986) Progress in the Chemistry of Organic Natural Products , vol.50 , pp. 27-56
    • Franck, R.W.1
  • 5
    • 0004230722 scopus 로고    scopus 로고
    • Cordell, G. A, Ed, Academic Press: London, Chap. 10
    • Szantay, C. In The Alkaloids, Vol. 50; Cordell, G. A., Ed.; Academic Press: London, 1998, Chap. 10.
    • (1998) The Alkaloids , vol.50
    • Szantay, C.1
  • 6
    • 0004230722 scopus 로고    scopus 로고
    • Cordell, G. A, Ed, Academic Press: London, Chap. 2
    • Lounasmaa, M.; Hankinen, P.; Westersund, M. In The Alkaloids, Vol. 52; Cordell, G. A., Ed.; Academic Press: London, 1999, Chap. 2.
    • (1999) The Alkaloids , vol.52
    • Lounasmaa, M.1    Hankinen, P.2    Westersund, M.3
  • 12
    • 0000884707 scopus 로고
    • Combining C-C π-Bonds
    • Paquette, L. A, Ed, Pergamon Press: Oxford
    • (a) Boger, D. L. Combining C-C π-Bonds, In Comprehensive Organic Chemistry, Vol. 5; Paquette, L. A., Ed.; Pergamon Press: Oxford, 1991, 451-512.
    • (1991) Comprehensive Organic Chemistry , vol.5 , pp. 451-512
    • Boger, D.L.1
  • 14
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    • Combining C-C π-Bonds
    • Paquette, L. A, Ed, Pergamon Press: Oxford, Chap. 7.3
    • Ziegler, F. E. Combining C-C π-Bonds, In Comprehensive Organic Synthesis, Vol. 5; Paquette, L. A., Ed.; Pergamon Press: Oxford, 1991, Chap. 7.3.
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    • Ziegler, F.E.1
  • 19
    • 34247178701 scopus 로고    scopus 로고
    • General Procedure for the Intramolecular Domino Knoevenagel Hetero-Diels-Alder Reaction: Method A: To a refluxing solution of activated ketones or 1,3-diones (1 mmol) in anhyd toluene (10 mL, the aldehydes 1a or 1b (1 mmol) was added and the reaction mixture was refluxed until the disappearance of the starting material as evidenced by TLC. After completion of the reaction, the solvent was evaporated in a rotary evaporator and the residue was subjected to flash column chromatography using hexane-EtOAc mixture. Method B: A solution of activated ketones or 1,3-diones (1 mmol) and the corresponding aldehyde (1 mmol) in anhyd toluene was irradiated with microwave (600 W power) until the TLC showed the disappearance of the starting material. After removal of the solvent, the crude reaction mixture was subjected to flash column chromatography (silica gel) to yield the product. Method C: A mixture of activated ketones or 1,3-dione 1 mmol, the corresponding
    • 13C NMR: δ = 22.92, 23.26, 37.20, 44.82, 49.17, 59.70, 110.94


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.