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Letters in Organic Chemistry
Volumn 6, Issue 5, 2009, Pages 372-376
Tandem generation and trapping of furo[3, 4-c]isoquinoline intermediates leading to the synthesis of phenanthridine ring systems
Author keywords

Azaisobenzofuran; Carbene complexes; Chromium; Diels Alder reaction; Phenanthridine
Indexed keywords

EID: 69549108467     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809788681347     Document Type: Article
Times cited : (7)
References (30)
  • 1
    • 0032849207 scopus 로고    scopus 로고
    • For a review on isobenzofurans, see:
    • For a review on isobenzofurans, see: (a) Friedrichsen, W. Adv. Heterocycl. Chem., 1999, 73, 1;
    • (1999) Adv. Heterocycl. Chem. , vol.73 , pp. 1
    • Friedrichsen, W.1
  • 6
    • 0142072614 scopus 로고    scopus 로고
    • For a related work on the carboaromatic series, see:
    • For a related work on the carboaromatic series, see: Luo, Y.; Herndon, J.W.; Cervantes-Lee, F. J. Am. Chem. Soc., 2003, 125, 12720.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12720
    • Luo, Y.1    Herndon, J.W.2    Cervantes-Lee, F.3
  • 7
    • 34548752261 scopus 로고    scopus 로고
    • Product class 11: phenanthridines
    • For a review of phenanthridine synthesis, see:
    • For a review of phenanthridine synthesis, see: (a) Keller, P.A. Product class 11: phenanthridines. Sci. Synth., 2005, 15, 1065.
    • (2005) Sci. Synth. , vol.15 , pp. 1065
    • Keller, P.A.1
  • 8
    • 84944031181 scopus 로고    scopus 로고
    • McKillop, A.E.; Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V.; Eds.; Elsevier: Oxoford
    • Balasubramanian, M.; Keay, J.G. In Comprehensive Heterocyclic Chemistry II, McKillop, A.E.; Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V.; Eds.; Elsevier: Oxoford, 1996, Vol.5, pp. 245-300.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.5 , pp. 245-300
    • Balasubramanian, M.1    Keay, J.G.2
  • 9
    • 56649086815 scopus 로고    scopus 로고
    • Some representative phenanthridine synthesis of this century include:
    • Some representative phenanthridine synthesis of this century include: (a) Della Ca', N.; Motti, E.; Catellani, M. Adv. Synth. Catal., 2008, 350, 2513;
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 2513
    • Della Ca, N.1    Motti, E.2    Catellani, M.3
  • 23
    • 85036808693 scopus 로고    scopus 로고
    • To a refluxing solution of 1-phenyl-3- trimethylsilylethynyl-4- isoquinoline carboxaldehyde (10) (200 mg, 0.60 mmol) and N-methylmaleimide (67 mg, 0.60 mmol) in THF (5 mL) was added a solution of carbene complex 1 (168 mg, 0.67 mmol) in THF (5 mL) over a period of 0.5 h. After the addition was complete, the mixture was heated to reflux for a period of 12 h. The mixture was allowed to cool to room temperature and then concentrated on a rotary evaporator. EtOAc (10 mL) was added and the residue was filtered through Celite (500 mg). The solvent was removed on a rotary evaporator, and the crude products were dissolved in ether (10 mL). To this solution of the crude product aqueous HCl (1: 1) (0.5 mL) was added and the mixture was stirred for 4 h at room temperature. The organic layer was then separated
    • +): 413.1501; found 413.1492.
    • Typical Experimental procedure for Preparation of Phenanthridine Derivative
  • 28
    • 85036822244 scopus 로고    scopus 로고
    • +): 370.1807; found 370.1801
    • +): 370.1807; found 370.1801.
  • 29
    • 85036806450 scopus 로고    scopus 로고
    • 2 (M + Na): 392.1626; found 392.1625
    • 2 (M + Na): 392.1626; found 392.1625.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.