634. The synthesis of some dialkylamino-2-quinolones

Bowman, R. E.; Grey, T. F.; Huckle, D.; Lockhart, I. M.; Wright, Malcolm

doi:10.1039/jr9640003350

Cited by 3 publications

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“…The reagents and solvents were used as obtained from the commercial sources. Compounds 1a , , 1d , 1e , 1f , 1h , 1j , 1k , , and 1l ,, were prepared as described in the literature. Column chromatography was carried out on Silica gel 60 (particle size 0.063–0.2 mm, activity acc.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…White solid, mp 183−186 °C. 1 H NMR (500 MHz, DMSO-d 6 ) δ 3.38 (s, 3H, H1′), 3.41 (s, 3H, H1‴), 5.64 (s, 1H, H3), 6.83 (d, 2H, J = 7.8 Hz, H2″, H6″), 6.96 (dd, 1H, J = 7.5, 7.5 Hz, H7), 7.01 (t, 1H, J = 7.3 Hz, H4″), 7.08 (dd, 2H, J = 7.7, 7.7 Hz, H3″, H5″), 7.10 (d, 1H, J = 8.0 H, H9), 7.26 (ddd, 1H, J = 7.7, 7.7, 1.2 Hz, H8), 7.38 (dd, 1H, J = 7.8, 1.0 Hz, H6); 13 (13), 120 (60), 119 (43), 118 (44), 92 (32), 91 (14), 77 (12)…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Synthesis of 1,4-Benzodiazepine-2,5-diones by Base Promoted Ring Expansion of 3-Aminoquinoline-2,4-diones

et al. 2016

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An unprecedented reactivity of 3-aminoquinoline-2,4-diones is reported. Under basic conditions, these compounds undergo molecular rearrangement to furnish 1,4-benzodiazepine-2,5-diones. The transformations take place under mild reaction conditions by using 1,1,3,3-tetramethylguanidine, NaOEt, or benzyltrimethylammonium hydroxide as a base. A proposed mechanism of the rearrangement and the conformational equilibrium of 1,4-benzodiazepine-2,5-dione rings are discussed.

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Section: Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of 1,4-Benzodiazepine-2,5-diones by Base Promoted Ring Expansion of 3-Aminoquinoline-2,4-diones

et al. 2016

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The chemistry of 2H‐3,1‐benzoxazine‐2,4(1H)‐dione (isatoic anhydride). 10. Reactions with ester enolates. Synthesis of 4‐hydroxy‐1‐methyl‐3‐prenyl‐2(1H)‐quinolinones, Crucial intermediates in the synthesis of quinoline alkaloids

Coppola¹

1983

Journal of Heterocyclic Chem

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N‐Methylisatoic anhydride reacts with the lithium enolates of esters to produce β‐ketoesters 4 in nearly quantitative yield. Thermal cyclization of these relatively unstable intermediates afford the corresponding 3‐substituted‐4‐hydroxy‐1‐methyl‐2(1H)‐quinolinones (5) in good yields. The reaction of the lithium enolate of 5‐methyl‐4‐hexenoic acid ethyl ester (14) with various nuclear substituted isatoic anhydrides gives 4‐hydroxyl‐methyl‐3‐prenyl‐2(1H)‐quinolinones 8, 9, and 18 which are highly desirable intermediates in the synthesis of a variety of quinoline alkaloids. Treatment of 18 with DDQ furnishes oricine in 73% yield.

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¹³C NMR investigation of some hetero‐ring substituted 2‐ and 4‐quinolone systems

Coppola¹,

Kahle²,

Shapiro³

1981

Org. Magn. Reson.

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A series of 2-and 4-quinolones substituted in the hetero-ring have been evaluated using 13C NMR techniques. Substituent effects are discussed as an aid to evaluation of potential tautonnerimtion in the 2-quinolone systems. The observed substituent shifts for systems having a hydroxy function at the 4-position in the 2-quinolones can be explained without implementing the tautomerism to a 4-quinolone.During the course of some synthetic investigations involving the preparation of substituted 2-and 4-quinolones, it became necessary to use 13C NMR for the analysis of the products. A search of the literature for model systems revealed that very little work has been done in this area, other than for the parent compounds and some ring methylated derivatives.' It seemed of interest to extend these studies to include compounds substituted in the hetero ring, such as 1 and 2 shown below.From the data given in Table 1 it can readily be observed that several of the I3C chemical shifts vary over a large range. The C-2 and C-3 chemical shifts, which range over 18ppm and 32ppm, respectively, can be explained on the basis of substituent shifts inherent to the type of substitution involved. The N-CH, and C-4 chemical shifts also show a large range, and in both cases the shifts are to higher field than the parent system. The upfield substituent shift reflects the steric environment of these carbons. Interestingly, the N-CH, resonance seems sensitive to electronic effects, as seen in a comparison of shifts for l c and Id. The remaining carbon chemical shifts are much less affected by substituents at C-2 and C-3, with C-4a and C-6 showing the largest variations. In all, the substituent chemical shifts for 1 appear to be unexceptional and, therefore, should be useful for the analysis of the tautomerism possibilities in the 2-quinolones discussed below. 4-QuinolonesThe chemical shift data are given in Table 1, and the system numbering is shown above. The assignments are relatively straightforward and were made by comparison with the parent compound and the unmethylated material previously assigned in the literature.' 2-Quinolones

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634. The synthesis of some dialkylamino-2-quinolones

Cited by 3 publications

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Synthesis of 1,4-Benzodiazepine-2,5-diones by Base Promoted Ring Expansion of 3-Aminoquinoline-2,4-diones

Synthesis of 1,4-Benzodiazepine-2,5-diones by Base Promoted Ring Expansion of 3-Aminoquinoline-2,4-diones

The chemistry of 2H‐3,1‐benzoxazine‐2,4(1H)‐dione (isatoic anhydride). 10. Reactions with ester enolates. Synthesis of 4‐hydroxy‐1‐methyl‐3‐prenyl‐2(1H)‐quinolinones, Crucial intermediates in the synthesis of quinoline alkaloids

¹³C NMR investigation of some hetero‐ring substituted 2‐ and 4‐quinolone systems

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634. The synthesis of some dialkylamino-2-quinolones

Cited by 3 publications

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Synthesis of 1,4-Benzodiazepine-2,5-diones by Base Promoted Ring Expansion of 3-Aminoquinoline-2,4-diones

Synthesis of 1,4-Benzodiazepine-2,5-diones by Base Promoted Ring Expansion of 3-Aminoquinoline-2,4-diones

The chemistry of 2H‐3,1‐benzoxazine‐2,4(1H)‐dione (isatoic anhydride). 10. Reactions with ester enolates. Synthesis of 4‐hydroxy‐1‐methyl‐3‐prenyl‐2(1H)‐quinolinones, Crucial intermediates in the synthesis of quinoline alkaloids

13C NMR investigation of some hetero‐ring substituted 2‐ and 4‐quinolone systems

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¹³C NMR investigation of some hetero‐ring substituted 2‐ and 4‐quinolone systems