Reactions of Carbonyl Ylides

Lown, J. William; Matsumoto, Kazuo

doi:10.1139/v71-577

Cited by 35 publications

(16 citation statements)

References 36 publications

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“…Conversion of a 5-azaindolizinol into the corresponding chloride has been achieved by refluxing the azaindolizinol with phosphorus oxychloride (POCl 3 ). [5,13] When the indolizinol 3 was subjected to refluxing POCl 3 , the chloroindolizine 8 was indeed formed, but only in low yield (attempts to make the chloride 8 by treatment of the indolizinol with triphenylphosphane dichloride were unsuccessful, however). Hence, we transformed the indolizinol 3 into the more reactive bromide 9 with triphenylphosphane dibromide [6] in dry acetonitrile.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1-Substituted 7-Cyano-2,3-diphenylindolizines and Evaluation of Antioxidant Properties

et al. 2000

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Protocols for the synthesis of novel 1‐substituted 7‐cyano‐2,3‐diphenylindolizines from the corresponding indolizinol have been developed, and the compounds’ abilities to act as antioxidants, i.e. to inhibit lipid peroxidation in vitro, have been examined. 1‐Bromo‐7‐cyano‐2,3‐diphenylindolizine 9 readily participates in Pd‐catalysed coupling reactions with organotin, organozinc, and organoboron reagents. Similar treatment of the corresponding indolizinyl triflate 6, on the other hand, resulted only in partial cleavage of the triflate back to the indolizinol, except in reaction with 1‐ethoxyethenyl(tributyl)tin. Here, the unexpected acetal (1‐ethoxyethoxy)indolizine 10 was formed. The structure of 10 was determined by single‐crystal X‐ray diffraction methods at 150 K. An alternative strategy for the introduction of substituents at C‐1 is by lithiation of the bromide 9 followed by reaction with electrophiles. The ability of the indolizine derivatives to inhibit lipid peroxidation in vitro was examined. Lipid peroxidation of boiled rat liver microsomes was induced by ascorbic acid/FeSO4 and peroxidation was determined by measuring the material reactive to thiobarbituric acid. In particular, the indolizinyl acetate 4 and the triflate 6 appear to be highly active antioxidants, with IC50 values below 1 μm in the bioassay.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 1-Substituted 7-Cyano-2,3-diphenylindolizines and Evaluation of Antioxidant Properties

et al. 2000

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“…A carbonyl addition product 73 (40% yield) had been identified in the reaction of diphenylcyclopropenone (8a) with pyridine 53 (equation 2). Interest in the chemical behavior of 8a made it desirable to explore the possibility of participation of a "conjugate addition" mode in the reacton of pyridine with appropriately substituting the nucleus with a second functional group capable of intercepting a reactive (ketene) intermediate.…”

Section: Reaction Of Cyclopropenones With Aminoaromaticsmentioning

confidence: 99%

The chemistry of enaminones, diazocarbonyls and small rings: our contribution

Kascheres¹

2003

J. Braz. Chem. Soc.

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“…[1,2] On irradiation or on thermal activation aziridines undergo ring opening to the corresponding azomethine ylides which can be trapped in [3+2] cycloadditions with various dipolarophiles, to form nitrogen containing five membered heterocycles. [3][4][5] Under photoinduced electron transfer (PET) conditions the aziridine is oxidized to the corresponding radical cation, which can react in a similar manner. [6][7][8][9][10] In the course of our investigations aimed at the applications of aziridines in organic synthesis [10,11] we became interested in the reactive intermediates of the [3+2] cycloadditions, i.e.…”

Section: Introductionmentioning

confidence: 99%