1955
DOI: 10.1002/cber.19550880125
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Die Oxydation von Alkylpyridinen mit Selendioxyd

Abstract: Die Oxydation von Alkylpyridinen durch Selendioxyd ohne Zusatz fremder Lösungs- bzw. Verdünnungsmittel gestattet die Gewinnung von Pyridincarbonsäuren. Das Verfahren eignet sich auch zur Darstellung von Pyridincarbonsäuren, die leicht Kohlendioxyd abspalten. Die selektive Eigenschaft des Selendioxyds, mit Alkylgruppen in 3-Stellung des Pyridinkernes nicht zu reagieren, bleibt dabei voll erhalten. Pyridin und Methylpyridin sowie Chinolin und Isochinolin bilden unter Wasserauschluß mit Selendioxyd kristallisiert… Show more

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Cited by 36 publications
(14 citation statements)
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“…The pure glyoxylic acids 2a – j (76%–54%) were obtained by column chromatography using ethyl acetate: n‐hexane (90:10) and characterized by melting points and FTIR similar to reported compounds. (Hatanaka & Ishimaru, 1973; Jerchel, Bauer, & Hippchen, 1955; Wadhwa et al., 2008).…”
Section: Methodsmentioning
confidence: 99%
“…The pure glyoxylic acids 2a – j (76%–54%) were obtained by column chromatography using ethyl acetate: n‐hexane (90:10) and characterized by melting points and FTIR similar to reported compounds. (Hatanaka & Ishimaru, 1973; Jerchel, Bauer, & Hippchen, 1955; Wadhwa et al., 2008).…”
Section: Methodsmentioning
confidence: 99%
“…They are commonly synthesized by the oxidation of 2-methylpyrazine, 3-picoline, 4-picoline, and 2-picoline, respectively. Different oxidizing agents such as air, nitric acid, , and selenium dioxide can be used for this type of oxidation. In air-oxidation the use of costly catalysts and highly corrosive promoters such as bromide salts in acetic acid solvent at elevated temperature makes the process somewhat complicated from both cost and design points of view.…”
Section: Introductionmentioning
confidence: 99%
“…On the basis of literature precedent for the lateral oxygenation of picolines, ix treatment of 9 with SeO 2 (2.5 equiv, 1,4-dioxane, 150 °C, 3 h) led to the formation of 11 (dubbed Boc- iso -complanadine B) as the major product. The observed selectivity for oxygenation likely arises because of the higher accessibility of the nitrogen in the 2,3,5-substituted pyridine ring as well as the potential stabilization of reactive intermediates x by both pyridine rings (see 10 ).…”
mentioning
confidence: 99%