Pyrylium Perchlorate Research Articles

Synthesis and absorption spectra of some 2,6‐disubstituted‐4‐(4‐dimethylaminophenyl)pyrylium perchlorates

Journal of Heterocyclic ChemistryVolume 11, Issue 3 p. 405-406 Note Synthesis and absorption spectra of some 2,6-disubstituted-4-(4-dimethylaminophenyl)pyrylium perchlorates G. A. Reynolds, G. A. Reynolds Research Laboratories, Eastman Kodak Company, Rochester, New York 14650Search for more papers by this authorJ. A. Van Allan, J. A. Van Allan Research Laboratories, Eastman Kodak Company, Rochester, New York 14650Search for more papers by this author G. A. Reynolds, G. A. Reynolds Research Laboratories, Eastman Kodak Company, Rochester, New York 14650Search for more papers by this authorJ. A. Van Allan, J. A. Van Allan Research Laboratories, Eastman Kodak Company, Rochester, New York 14650Search for more papers by this author First published: June 1974 https://doi.org/10.1002/jhet.5570110325Citations: 9AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article.Citing Literature Volume11, Issue3June 1974Pages 405-406 RelatedInformation

Synthesis of pyrylium and pyridine derivatives of benzofuran

Acylation of benzo[b]-2-furyl acetone was used to synthesize 2,9-disubstituted benzofuro[3,2c] pyrylium perchlorates, which were converted in high yields to the corresponding benzofuro-[3,2-c]pyridines. The molecular diagram of the pyrylium cation is examined. The IR, UV, and NMR spectra of the synthesized compounds are discussed.

The spectroscopy of pyrylium salts

The spectra of pyrylium perchlorate, various alkyl and aromatic derivatives, and cyanine-like dyes derived from pyrylium salts are discussed. These molecules are closely related to molecules which belong to the C 2v point group, and the existence of the symmetry permits a more detailed discussion of the spectra than has been attempted heretofore.

Synthesis of 2-aryl-3,4,5,6-bis(trimethylene) pyrylium salts and the corresponding pyridine bases

2-Aryl-3,4,5,6-bis(trimethylene)pyrylium perchlorates were obtained by acylation of cyclopentylidenecyclopentanone with aromatic acid chlorides in the presence of anhydrous aluminum chloride with subsequent treatment with 70% perchloric acid. The synthesized salts were converted to the corresponding pyridine bases.

Formation of benzanilides from pyrylium salts and 2-phenyl-Δ2-oxazolin-5-one

The base-catalysed reaction of 2-phenyloxazolin-5-one with five tri- or tetra-substituted pyrylium perchlorates yielded derivatives of benzanilide; intermediate unsaturated azlactones were isolated in two cases. 2,6-Di-phenylpyrylium perchlorate gave a 4-pyranylideneoxazolinone.

A novel synthesis of 6-phenyl- and 6-o-tolyl-dibenzo[b,d]pyrylium perchlorates

9-Phenyl- and 9-o-tolyl-fluorene are converted into 6-phenyl- and 6-o-tolyl-dibenzo[b,d]pyrylium perchlorates, respectively, by acid-catalysed rearrangement of the 9-hydroperoxides.

Synthesis of β-carbolinyl sugars

Decomposition of penta- O-acetyl-l-deoxy-l-diazo- keto- D- gluco-heptulose, in the presence of N-methylindole and copper powder as catalyst, results in the formation of penta- O-acetyl-l-deoxy-l-( N-methylindol-3-yl)- keto- D- gluco-heptulose ( 1). Compound 1 is acylated by carboxylic anhydrides at C-2 of the N-methylindole moiety, and cyclisation of the intermediate diketone, in the presence of 70% perchloric acid, gives indolo-[2,3- c]-pyrylium perchlorates. With aqueous ammonia, these perchlorates are easily transformed into β-carbolinyl sugars that are close structural analogues of the indole alkaloids harmane, harmine, and melinonine.

Ultraviolet absorption spectrum of pyrylium perchlorate

The bathocromic shift observed in the ultraviolet spectra of sym-trimethyl derivatives of benzene, pyridine, pyridinium, and pyrylium is caused in equal measure by the heterocycle and by the substituents.