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Volumn 65, Issue 17, 2009, Pages 3378-3391

Novel chemistry of β-carbolines. Expedient synthesis of polycyclic scaffolds

Author keywords

Carbolines; Diels Alder; Domino reactions; Metathesis; Rearrangements

Indexed keywords

ALKALOID; ALKALOID DERIVATIVE; ALKYNE DERIVATIVE; ALLYL BETA CARBOLINE DERIVATIVE; BETA CARBOLINE; ETHYNYL BETA CARBOLINE DERIVATIVE; HETEROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON; PROPARGYL BETA CARBOLINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL BETA CARBOLINE DERIVATIVE;

EID: 62849085967     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.051     Document Type: Article
Times cited : (34)

References (47)
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    • note
    • The reaction of tryptamine with ethylformate gives a formamide, which when treated with NaH and allyl bromide gives a mixture of 1, 2, and 3. With a careful selection of the reaction conditions mono- or diallyl products can become major products selectively. Compound 5 was obtained by reaction with excess propargyl bromide. See Supplementary data for details.
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    • note
    • Alternatively to the synthesis of 6a and 6b from 1, as this starting material is obtained in low yield, dihydro-β-carboline was protected as the tosyl derivative, and reacted with an alkynylmagnesium bromide. The resulting 1-ethynyl or 1-(1-propynyl)-9-tosyltetrahydro-β-carboline was allylated giving 6a and 6b in a global yield of 42 and 49%, respectively.
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    • See:
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    • Although it was generally accepted that enyne metathesis reactions follow an yne-ene pathway involving initial coordination of the alkyne to the metal, there is actually evidence for an ene-yne pathway, see: and references cited therein
    • Although it was generally accepted that enyne metathesis reactions follow an yne-ene pathway involving initial coordination of the alkyne to the metal, there is actually evidence for an ene-yne pathway, see:. Sohn J.H., Kim K.H., Lee H.Y., No Z.S., and Ihee H. J. Am. Chem. Soc. 130 (2008) 16506-16507 and references cited therein
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    • These kinds of oxidations have been used for the synthesis of aromatic compounds. See:. Donohoe T.J., Fishlock L.P., and Procopiou P.A. Chem.-Eur. J. 14 (2008) 5716-5726
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    • 4, following a procedure described in: Unfortunately we observed no reaction after 3 days, recovering the starting material unchanged
    • 4, following a procedure described in:. Yang Q., Xiao W.J., and Yu Z. Org. Lett. 7 (2005) 871-874 Unfortunately we observed no reaction after 3 days, recovering the starting material unchanged
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    • note
    • 2. This reaction gave a mixture of 15a, 37a, 35a, and 35b, in the following ratios (2:3:2:1). From this mixture, 15a (10%), 37a (27%), and 35a (13%) were isolated.
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    • For a recent review on Stevens rearrangement, see:. Vanecko J.A., Wan H., and West F.G. Tetrahedron 62 (2006) 1043-1062
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.