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Volumn , Issue 4, 2008, Pages 505-508

A facile synthesis of telisatin A via microwave-promoted annulation and reformatsky reaction

Author keywords

Annulation; Dioxoaporphine; Dioxopyrrolo 2,1 a isoquinoline; Microwave; Reformatsky reaction

Indexed keywords

APORPHINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; PYRUVIC ACID DERIVATIVE; TELISATIN A; UNCLASSIFIED DRUG;

EID: 40949157622     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042764     Document Type: Article
Times cited : (5)

References (27)
  • 1
    • 0003947866 scopus 로고    scopus 로고
    • Ravindranath, B, Ed, Harwood Academic Publishers: Amsterdam
    • Bentley, K. W. The Isoquinoline Alkaloids; Ravindranath, B., Ed.; Harwood Academic Publishers: Amsterdam, 1998, 158.
    • (1998) The Isoquinoline Alkaloids , pp. 158
    • Bentley, K.W.1
  • 22
    • 40949136608 scopus 로고    scopus 로고
    • Synthesis of 2,3-Dioxopyrrolo[2,1-a]isoquinoline 2; Typical Procedure (Conditions C, A mixture of imines 4 (0.1 mmol, aryl pyruvates 5 (0.1 mmol) and NaOMe (0.1 mmol) in DMF (1 mL) was irradiated using microwave. The microwave run time was set to 2 min, with power at 300 W, temperature at 150°C, and pressure at 100 psi, and the conditions were maintained for 10 min. The reaction was quenched with H2O and extracted with EtOAc, dried (Na2SO4) and evaporated in vacuo to yield a red residue. The residue was purified by column chromatography, affording crystals of 2 after recrystallization in moderate yields (54-78, Conditions D: A mixture of imines 4 (0.1 mmol, aryl pyruvates 5 (0.1 mmol, copper powder (0.1 mmol) and zinc powder (0.1 mmol) in DMF (1 mL) was irradiated using microwave. The microwave run time was set to 2 min, with power at 300 W, temperature at 150°C, and pressure
    • 5: 444.0447; found: 444.0449.
  • 23
    • 84949994976 scopus 로고    scopus 로고
    • For microwave irradiation, see: a, Mannhold, R, Kubinyi, H, Folkers, G, Eds, Wiley-VCH: Weinheim
    • For microwave irradiation, see: (a) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Mannhold, R.; Kubinyi, H.; Folkers, G., Eds.; Wiley-VCH: Weinheim, 2005.
    • (2005) Microwaves in Organic and Medicinal Chemistry
    • Kappe, C.O.1    Stadler, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.