A novel synthesis of 1,4-dihydrobenzo[c]-1,5-naphthyridin-2(3H)-ones from pyrrolo[1,2-b]isoquinolines

Martin, Lawrence L.; Scott, Susan J.; Agnew, Marc N.; Setescak, L. L.

doi:10.1021/jo00369a026

Cited by 27 publications

(7 citation statements)

References 3 publications

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“…The reaction is rationalized by involving either the protonated ketone 8 which rearranges itself to the more stable iminium salt 9b by a hydrogen shift or the protonated enol 9a stabilized as the iminium salt 9b (Scheme 3). An aromatization of 9b gives the acylpyridinium intermediate 10 similar to that postulated with an amino group in place of hydroxyl group 16 . Rearrangement of 10, with the loss of a proton, provides the lactones 7.…”

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confidence: 71%

New fused lactones from indolizinediones via N-acyliminium ions

1998

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N-Arylmethylphthalimidine-3-carboxylates 3 are good precursors for the synthesis of ketones 5a,b or enols 6c-e which upon acidic treatment led to lactones 7 via an Nacyliminium ion. Gilvocarcin 1 and related compounds are metabolites of certain Streptomyces species and constitute a novel class of aryl C-glycoside antibiotics 2. These compounds share a common tetracyclic aromatic nucleus, 6H-benzo[d]naphto[l,2-b]pyran-6-one to which sugars are attached at the C 4 position. Recently, isosteres of defucogilvocarcin have been described 3 , in which the vinylbenzene moiety is replaced by a benzofuran moiety. We wish to report herein our results concerning the introduction of a heterocyclic system in place of the naphthalenic system in related compounds of type A. Furthermore that latter species is also closely related to alkaloids possessing a benzopyranisoquinoline skeleton. Literature 4-7 shows a variety of examples of these types of compounds, which in many cases exhibit a remarkable physiological activity (antiinflammatory, dopaminergic, antidepressive). Finally, the synthesis of [1]benzopyran[4,3-c]isoquinoline derivatives have been reported 8 very recently by employing isoflavone as the starting material.

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confidence: 71%

New fused lactones from indolizinediones via N-acyliminium ions

1998

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“…With ketone 148 e, the oxime configuration was inverted and only the 1,4-diazepine isomer 154 e was obtained (thiophene migration). [56] With thienoindolizidinones 150 b-e as starting materials, the result of the reaction is quite different. [53] As observed with the previous series, the Beckmann rearrangement of the antipiperidinyl oxime led to the 1,3-diazepine isomer, whereas the other oxime isomer did not lead to the corresponding 1,4diazepine but to naphthyridine 153, thanks to a Semmler-Wolff aromatization followed by a rearrangement of the oxopyrrolidine ring (Scheme 37A).…”

Section: Conflict Of Interestmentioning

confidence: 99%

“…Thus, in the case of ketones 148 b – d , only the corresponding anti ‐piperidinyl oximes were formed, allowing the formation of the corresponding 1,3‐diazepine as the exclusive product (alkyl migration). With ketone 148 e , the oxime configuration was inverted and only the 1,4‐diazepine isomer 154 e was obtained (thiophene migration) [56] …”

Section: 3‐diazepine Synthesis By Ring Transformationmentioning

confidence: 99%

1,3‐Diazepine Derivatives: Strategies for Synthesis

2021

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“…We recently described the synthesis of 1,2,3,5,10,10a-hexahydrobenz[]]indolizin-3,10-dione (1) (Rigo & Kolocouris, 1984). Martin, Scott, Agnew & Setescak (1986) found that the treatment of the oxime of this ketone under Beckman conditions (PPA, 373 K) gave 1,4-dihydrobenzo[c]-l,5-naphthyridin-2(3H)-one (2). In an attempt to obtain the oxygenated analogue (3) of the lactam (2), the ketone (1) was subjected to the same treatment.…”

Section: C(6)---c(5a)--c(9a) 1196 (3)mentioning

confidence: 99%

Structure of 3,5-dihydrobenz[f]indolizin-3-one

Lamiot¹,

Baert²,

Abdelhalim³

et al. 1991

Acta Crystallogr C

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Abstract. C12H9NO, Mr = 183.2, triclinic, P1, a = 8.837 (6), b = 7-910 (6), c = 6.903 (5) A, a = 108.2 (1), /3 = 77.7 (1), y= 101"4 (1) °, V= 443"4 A 3, Z = 2, Dx = 1"372 g cm -3, Mo Kce, A = 0.71069 ,£,,/z = 0-5 cm-1, F(000) = 192, T= 293 (2) K, R = 0.054 for 1626 reflections with I___3tr(/). Elemental analysis and the mass spectrum of the compound, and one-and two-dimensionally correlated NMR spectra are in good agreement with the results of the structure analysis, in which the molecule is found to be roughly planar.Experimental. As described in the literature (Rigo & Kolocouris, 1984), fine powder of (1) (lg, 4.97 mmol) was quickly added to hot (413 K), stirred polyphosphoric acid (20 g). The mixture was vigorously stirred for 1 h. The hot mixture was decanted over crushed ice (150 ml) and the aqueous solution was extracted with dichloromethane. The organic phase was washed with water, dried over K2CO3, * To whom correspondence should be addressed.0108-2701/91/040888-03503.00 filtered and concentrated to give 70% yield of a red powder, which was then treated overnight in dichloromethane at room temperature, with activated carbon, filtered and concentrated in part; pure yellow crystals of (4), which turned red in air, were obtained by slow evaporation of the solvent at 437 K.

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A novel synthesis of 1,4-dihydrobenzo[c]-1,5-naphthyridin-2(3H)-ones from pyrrolo[1,2-b]isoquinolines

Cited by 27 publications

References 3 publications

New fused lactones from indolizinediones via N-acyliminium ions

New fused lactones from indolizinediones via N-acyliminium ions

1,3‐Diazepine Derivatives: Strategies for Synthesis

Structure of 3,5-dihydrobenz[f]indolizin-3-one

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