New routes to condensed polynuclear compounds—VII

Kessar, S. V.; Gopal, R.; Singh, Mahesh Kumar

doi:10.1016/s0040-4020(01)99391-3

Cited by 40 publications

(5 citation statements)

References 30 publications

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“…While the dihydrophenanthridine derivatives are present in the skeleton of a wide number of biologically active compounds, only a few synthetic methods for this class of compounds have been reported in the literature. Furthermore, the reported methods generally suffer from low yields due to the limited functional group tolerance and the undesired in situ oxidation …”

mentioning

confidence: 99%

Synthesis of Dihydrophenanthridines and Oxoimidazolidines from Anilines and Ethylglyoxylate via Aza Diels–Alder Reaction of Arynes and KF-Induced Annulation

et al. 2016

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The transition-metal-free multicomponent coupling of arynes, anilines, and ethylglyoxylate, proceeding via an inverse electron-demand aza Diels-Alder cycloaddition and N-arylation, has been demonstrated. This protocol allows rapid access to N-aryl dihydrophenanthridine derivatives in moderate to high yields at room temperature from readily available starting materials. In addition, an unprecedented fluoride induced annulation of ethyl(arylimino)acetates led to the formation of highly functionalized oxoimidazolidine derivatives in good yields under mild conditions.

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mentioning

confidence: 99%

Synthesis of Dihydrophenanthridines and Oxoimidazolidines from Anilines and Ethylglyoxylate via Aza Diels–Alder Reaction of Arynes and KF-Induced Annulation

et al. 2016

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“…The mixture was further stirred at room temperature for 1.5 h and then evaporated under reduced pressure. 8;H,7.6;N,3.4. The ethereal solution was dried (K2C03) and evaporated to give a yellow oil * (9. This material was characterized as a picrate: yellow prisms, m.p.…”

Section: -(34-dimethoxyphenyl)-6-hydroxy-7-methoxy-34-dihy-mentioning

confidence: 99%

“…[275][276][277]73.4;H,6.2;N,3.7. 8, for C,,H,,NO,: C,73.2;H,6.1;N,3.7%); G(CF,CO,H) 1.57 (6 H,d,J 6.0 Hz,CHMe,) Hz,8.19 (1 H,s,ArH),8.24 (1 H,s,ArH),8.52 (1 H,d,J 9.0 Hz,and 9.42 $ (1 H,d,J 8.0 Hz,.…”

Section: O-isopropylnorfagaronine (2-isopropoxy-389-trimethoxybenzomentioning

confidence: 99%

Studies on the chemical constituents of rutaceous plants. Part 62. Efficient synthesis of fagaronine, a phenolic benzo[c]phenanthridine alkaloid with antileukaemic activity

Ishii¹,

Chen²,

Ishikawa³

1987

J. Chem. Soc., Perkin Trans. 1

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Fagaronine ( 2 ) , an antileukaemic hydroxybenzo[c] phenanthridine alkaloid, has been synthesized from the chalcone (4a) according to the synthetic sequence (Schemes 1-4). During the synthesis, the hydroxy group was protected in the form of its isopropoxy derivative.It is well known that fully aromatised quaternary benzo[c]phenanthridine alkaloids occur naturally in Rutaceous and Papaveraceous plants. These alkaloids, particularly nitibne 3b (l), a non-phenolic base, and fagaronine 3c*4 (2), a phenolic one, have attracted attention because of their antileukaemic properties.3( 1 ) R',R2 = CHz( 2 ) R 1 = H , R 2 = M e

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“…With the aim of synthesizing new antitumoral compounds, we attempted to replace the benzo[c]phenanthridine ring system by a benzo[c] [1,8]phenanthroline [19]. We report in this paper our results on the synthesis of the benzo[c] [1,8]phenanthrolin-6-one 3 via the key cyclization of N-(isoquinol-5-yl)-2-bromo-4,5dimethoxybenzamide (4) either using the Kessar benzyne cyclization [20,21] or a palladium-assisted intramolecular biaryl coupling reaction [22].…”

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confidence: 99%

Synthesis of Benzo[c][1,8]phenanthrolin‐6‐one Through Cyclization of N‐(Isoquinol‐5‐yl)‐2‐bromo‐benzamide Derivatives.

Prado¹,

Michel²,

Tillequin³

et al. 2007

ChemInform

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Synthesis of Benzo[c][1,8]phenanthrolin-6-one Through Cyclization of N-(Isoquinol-5-yl)-2-bromo-benzamideDerivatives. -The access to benzophenanthrolinone (VII) involves the key cyclization of isoquinolyl dimethoxybenzamide (III) either using a benzyne intermediate cyclization or a palladium-assisted intramolecular biaryl coupling reaction. The first cyclization attempt yields only traces of target compounds (VII) along with the unexpected compound (IV), which is the result of an internal Diels-Alder reaction between the benzyne intermediate and the isoquinoline ring system. In the course of an alternate preparation of (III) using the carbodiimide EDC, the bisbenzamide (VIII) is obtained as an already protected precursor to give under the previous palladium-assisted cyclization conditions the target (VII) in a much improved yield. -(PRADO, S.; MICHEL, S.; TILLEQUIN*, F.; KOCH, M.; J. Heterocycl.

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New routes to condensed polynuclear compounds—VII

Cited by 40 publications

References 30 publications

Synthesis of Dihydrophenanthridines and Oxoimidazolidines from Anilines and Ethylglyoxylate via Aza Diels–Alder Reaction of Arynes and KF-Induced Annulation

Synthesis of Dihydrophenanthridines and Oxoimidazolidines from Anilines and Ethylglyoxylate via Aza Diels–Alder Reaction of Arynes and KF-Induced Annulation

Studies on the chemical constituents of rutaceous plants. Part 62. Efficient synthesis of fagaronine, a phenolic benzo[c]phenanthridine alkaloid with antileukaemic activity

Synthesis of Benzo[c][1,8]phenanthrolin‐6‐one Through Cyclization of N‐(Isoquinol‐5‐yl)‐2‐bromo‐benzamide Derivatives.

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