Quinolone, 4-methoxy-l-methyl

The wood of this plant yielded, among other and neutral products, 4-methoxy-l-methyl-2-quinolone (mp 99-103°). The bark yielded nitidine, aricine, chelerythrine, isolated as derivatives, and oxynitidine (mp 283-285°). In addition l-( + )-armepavine metho salt was also found (171). 

Haplopine (1 R1 = H, R2 = OH, R3 = OMe) 4-Methoxy- l-methyl-2-quinolone Robustine Skimmianine... 

Non-hemiterpenoid Quinolines.—New sources of the simple quinolines 4-methoxy-l-methyl-2-quinolone and its 8-methoxy-derivative (folimine) have been reported the former was isolated from Myrtopsis sellingii9 and from Zanthoxylum cuspidatum,16 and folimine was shown to be a constituent of Haplophyllum perforatum.5 The latter species also contains foliosidine (9), previously isolated from H. foliosum. The micro-organism Pseudomonas aertiginosa has been shown to contain 2-(hept-l-enyl)-4-quinolone (12).10 The structure of the alkaloid was established by n.m.r. and mass spectroscopy and by its synthesis from aniline and the j3-keto-ester Me(CH2)4CH=CHC0CH2C02Me. 

The UV-spectrum of lunacridine, which is unchanged in acid or alkali, is consistent with the presence of a 2-quinolone system the batho-chromic shift of the maxima at 284 and 294 m/x, in comparison with those of 4-methoxy-l-methyl-2-quinolone (268 and 278 m/a), can be attributed... 

Methoxy-l-methyl-2-quinolone was isolated from the stem bark 132). 

Methoxy-l-methyl-2-quinolone (1) was isolated from Hesperethusa crenulata M. Roem. (12) and from the wood of Fagara boninensis (13). The alkaloid folimine from Haplophyllum foliosum Vved. (14) was identified as 4,8-dimethoxy-l-methyl-2-quinolone (2), which had been obtained earlier during the degradation of foliosine (Volume IX, p. 225). Folifidine from H. dubium Eug. Kor (15) and from H. foliosum (16) is the 8-hydroxy-2-quinolone 3. 

Another 4-methoxy-l-methyl-2-quinolone (10) was isolated from the roots of Spathelia sorbifolia L. (25). The constitution of the alkaloid was established by spectroscopy and confirmed by dimethylation of quinolone 9 with dimethyl sulfate in dimethylformamide. 

Methoxy-l-methyl-2-phenyl-4-quinolone (XXVIII) C17H15NO2 198-200 0 12... 

Edulinine from Casimiroa edulis may be formed from (+)-N-methylplatydesminium salt during isolation. (+)-Edulinine from Pelea barbigera is certainly an artifact, and was obtained only when base was employed during isolation the precursor, presumably (—)-JV-methyl-platydesminium salt, could not be detected (43). ( )-Edulinine is conveniently prepared by reaction of 4-methoxy-l-methyl-3-(3-methylbut-2-enyl)-2-quinolone with m-chloroperbenzoic acid and then with aqueous base, without isolating intermediates (2). 

The water insoluble bases, together with those recovered from the mother liquors of the l-methyl-2-quinolone hydrochloride, are heated with 40 cc. of fuming hydrochloric add in a sealed tube at 175 for 2.5 hours, whweby the 4-methoxy-2-n-amyl-... 

A soln. of 4-hydroxy-8-methoxy-l-methyl-3-(3-methylbut-2-enyl)-2-quinolone in lerf-butanol containing coned. H2SO4 treated with excess peroxylauric acid and stored 3 days at 18° ( ) -balfourodine. Y 95%. E. A. Clarke and M. F. Grundon,... 

The scope of this approach was widened by the observation of excellent enantioselectivities in inter-molecular [2-i2]-photocycloaddition reactions with various alkenes. 4-Methoxy-2-quinolone 27 was converted with high chemo- and regioselectivity to cyclobutanes 29 and 30 in the presence of an excess of alkene. With 4-penten-l-ol 28a, allyl acetate 28b, methyl acrylate 28c, and vinyl acetate 28d, the exo-diastereomers 29a-d were formed with high simple diastereoselectivity and high yields (80 to 89%). Under optimized irradiation conditions (2.4 eq. of host 21 or enr-21,-60"C), high enantiomeric excesses were achieved in all instances, as depicted in Scheme 11 these enantiomeric excesses are unprecedented for an intermolecular photochemical reaction. As in the intermolecular case, host 21 induced Re-attack at carbon C3, and host e r-21 induced a St-attack. 

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