Analgesics. Some Substituted 2,3-Dihydro-4-quinolones<sup>1</sup>

Atwal, M. S.; Bauer, Leopold; Dixit, Shalini; Gearien, James E.; Morris, Ralph W.

doi:10.1021/jm00329a004

Cited by 23 publications

(8 citation statements)

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“…This reaction was run using 75 mg (0.50 mmoles) of 8 and the general procedure given above for the preparation of 10a . This compound (72 mg, 61%) was isolated as a light yellow solid, mp 111–114°C [16]. IR: 1673 cm −1 ; 1 H NMR δ 7.93 (dd, 1H, J = 7.8, 1.8), 7.39–7.24 (complex, 6H), 6.72 (t, 1H, J = 8.0), 6.70 (d, 1H, J = 8.4), 4.57 (s, 2H), 3.60 (t, 2H, J = 7.0), 2.75 (t, 2H, J = 7.0); 13 C NMR: δ 193.5, 151.7, 137.2, 135.5, 128.8, 128.2, 127.4, 126.7, 119.8, 117.0, 113.4, 55.2, 49.4, 38.0; ms: m/z 146 (M + ‐C 7 H 7 ).…”

Section: Methodsmentioning

confidence: 67%

1‐Alkyl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem Michael‐S_NAr annulation reaction

Bunce¹,

Nago²

2009

Journal of Heterocyclic Chem

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magnified imageA tandem Michael‐SNAr annulation reaction has been developed for the synthesis of 1‐alkyl‐2,3‐dihydro‐4(1H)‐quinolinones. Success in the reaction followed expected electronic effects for the final SNAr ring closure. Treatment of doubly activated 1‐(2‐fluoro‐5‐nitrophenyl)‐2‐propen‐1‐one with primary amines in N,N‐dimethylformamide at 50°C for 24 h provided 2,3‐dihydro‐4(1H)‐quinolinones in 67–78% yields. Singly activated 1‐(2‐fluorophenyl)‐2‐propen‐1‐one reacted similarly, but failed to undergo the final ring closure with hindered or aromatic amines. Finally, 1‐(2‐fluoro‐5‐methoxyphenyl)‐2‐propen‐1‐one, with one activating and one deactivating group on the ring, gave only simple 1,4‐addition products. J. Heterocyclic Chem., (2009).

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Section: Methodsmentioning

confidence: 67%

1‐Alkyl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem Michael‐S_NAr annulation reaction

Bunce¹,

Nago²

2009

Journal of Heterocyclic Chem

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“…For example, compounds A and B are known to exhibit significant cytotoxicity against a panel of human tumor cell lines [1, 2] . Compounds C can serve as a valuable molecules with potent analgesic activities [3] . Due to their intriguing scaffolds, a large number of synthetic approaches for the construction of 2,3‐dihydroquinolin‐4(1 H )‐ones have been reported [4] .…”

Section: Methodsmentioning

confidence: 99%

“…[1,2] Compounds C can serve as av aluable molecules with potent analgesic activities. [3] Due to their intriguing scaffolds, al arge number of synthetic approaches for the construction of 2,3-dihydroquinolin-4(1H)-ones have been reported. [4] However,m ost of these methodologies rely on the use of specific type of substrates.…”

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confidence: 99%

“…plished in four steps (Scheme4). The iodination of benzo[d] [1,3]dioxol-5-amine 6 led to the iodide 7 in 87 %y ield, which was then treated with 2-pyridylsulfonyl chloride to give the sulfonamide 8 with ah igh yield of 90 %. When 8 and 3-fluorostyrene weres ubjected to the standard conditions, the (N-SO 2 Py)-protected compound 9 was achieved in an excellent yield (93 %).…”

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confidence: 99%

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Chelating Group Enabled Palladium‐Catalyzed Regiodivergent Carbonylative Synthesis of 2,3‐Dihydroquinolin‐4(1H)‐ones

Ying

Wang

Yao

et al. 2020

Chemistry A European J

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An ew procedure on palladium-catalyzedc arbonylative cyclization of N-(2-pyridyl)sulfonyl (N-SO 2 Py)-2iodoanilines with terminal alkenes has been developed for the rapid construction of dihydroquinolin-4(1H)-ones caffolds. Enabled by the chelatingg roup and using benzene-1,3,5-triyl triformate (TFBen) as the CO source, both aromatic and aliphatic alkenes were smoothly transformed into the corresponding 2,3-dihydroquinolin-4(1H)-ones in good yields with excellent regioselectivities. Notably,t he reaction of aromatic alkenes produces 2-aryl-2,3-dihydroquinolin-4(1H)-ones, while 3-alkyl-2,3-dihydroquinolin-4(1H)-ones were obtained when aliphatic alkenes were used. This protocol has been appliedi nt he synthesiso f antitumora gent A as well. Scheme3.Removal of the N-SO 2 Py directing group. Scheme4.Synthesis of the antitumoragent A. Scheme5.Preliminarymechanistic studies. Scheme6.Plausible mechanism.

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“…Isocryptolepine 2: C,,H,,N2; IR (KBr) Fm- ': 1644': , 1617': , 1460': , 1354': , 1242': , 1123 232 (Mt, loo%), 217 (16) Synthesis of isocryptolepine. Isocryptolepine was obtained by the Fisher indole cyclization of the phenylhydrazone of Nmethyl 2,3-dehydro-4-quinolone which was prepared from propiolactone and N-methyl aniline as described previously (Atwal et al, 1965).…”

Section: Methodsmentioning

confidence: 99%

Antimalarial Activity of Cryptolepine and Isocryptolepine, Alkaloids Isolated from Cryptolepis sanguinolenta

Grellier¹,

Ramiaramanana²,

Millerioux³

et al. 1996

Phytother. Res.

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Cryptolepis sanguinolenta extracts are currently used by African herbalists to cure malaria but the compounds involved in its antimalarial activity have not been identified. Two alkaloids, cryptolepine and isocryptolepine, have been isolated from the roots of C. sunguinolenta and their antimalarial activity evaluated. Both alkaloids possess intrinsic inhibitory activity against the human malaria parasite, Plasmodium fakiparum in vitro, whatever the chloroquine-resistance status of the strains used. Cryptolepine was slightly more efficient for parasite killing with an ICs in the range of 0.2 to 0.6 p~ compared with an ICso of about 0.8 PM for isocryptolepine. The antimalarial activity of cryptolepine was confirmed in vivo on the rodent malarial parasites Plasmodium vinckei petleri and Plasmodium berghei ANKA.

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Analgesics. Some Substituted 2,3-Dihydro-4-quinolones¹

Cited by 23 publications

References 0 publications

1‐Alkyl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem Michael‐S_NAr annulation reaction

1‐Alkyl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem Michael‐S_NAr annulation reaction

Chelating Group Enabled Palladium‐Catalyzed Regiodivergent Carbonylative Synthesis of 2,3‐Dihydroquinolin‐4(1H)‐ones

Antimalarial Activity of Cryptolepine and Isocryptolepine, Alkaloids Isolated from Cryptolepis sanguinolenta

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Analgesics. Some Substituted 2,3-Dihydro-4-quinolones1

Cited by 23 publications

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1‐Alkyl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem Michael‐SNAr annulation reaction

1‐Alkyl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem Michael‐SNAr annulation reaction

Chelating Group Enabled Palladium‐Catalyzed Regiodivergent Carbonylative Synthesis of 2,3‐Dihydroquinolin‐4(1H)‐ones

Antimalarial Activity of Cryptolepine and Isocryptolepine, Alkaloids Isolated from Cryptolepis sanguinolenta

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Analgesics. Some Substituted 2,3-Dihydro-4-quinolones¹

1‐Alkyl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem Michael‐S_NAr annulation reaction

1‐Alkyl‐2,3‐dihydro‐4(1H)‐quinolinones by a tandem Michael‐S_NAr annulation reaction