An unexpected ring transformation of (Z )-3-benzyl-2-(nitromethylene)thiazolidine

Szabadkai, István; Harsányi, Kálmán; Bihari, M.; Rényei, M.; Rácz, György

doi:10.1039/a803823f

Cited by 3 publications

(1 citation statement)

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“…For example, the reaction of compound 118 with an excess of sodium nitrite in aqueous acetic acid gives the dioxime 119 as the only product [110] Under the condition of nitrosation (NaNO 2 /AcOH/pyridine/H 2 O) 1,5-benzothiazepine-2,4-dione 123 is converted into 2-hydroxyimino-1,4-benzothiazin-3(4H)-one 124 (yield 17%) and 2H-1,4-benzothiazine-3,4-dihydro-3-oxo-2-carboxylic acid 125 (45%) [112]. The synthesis of 1,4-thiazine oximes was realized by the cyclization of derivatives of 2-aminoethanethiols or 2-aminothiophenol with ethyl 2-chloro-2-(hydroxyimino)acetate [113][114][115], ethyl nitroacetate [116], or nitroacetone [117]. Thus, 2-aminoethanethiol 126 and ethyl chloro(hydroxyimino) acetate in an alkaline medium give 2-hydroxyiminotetrahydro-1,4-thiazin-3-ones 127 with yields of up to 83%.…”

Section: -Thiazine Aldoximes Ketoximes and Amidoximesmentioning

confidence: 99%

Oximes of six-membered heterocyclic compounds with two or three hetero-atoms: I. Synthesis and structure (review)

Абеле

Lukevics

2009

Chem Heterocycl Comp

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Data on methods for the production of and on the structure of pyridazine, pyrimidine, pyrazine, triazine, oxazine, thiazine, oxadiazine, and thiadiazine aldoximes, ketoximes, and amidoximes, and their derivatives are reviewed.The oximes of heterocyclic compounds with two or three heteroatoms are widely used as intermediates in fine organic synthesis. In this review the basic methods for the synthesis of pyridazine, pyrimidine, pyrazine, triazine, oxazine, thiazine, oxadiazine, and thiadiazine aldoximes, ketoximes, and amidoximes and their derivatives are summarized. The basic methods for investigation of the structure of the oximes of six-membered heterocyclic compounds with two or three heteroatoms are discussed in relation to isomerism. The reactions and biological activity of the oximes of heterocyclic compounds with two or three heteroatoms will be examined in the second part of the review.

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Section: -Thiazine Aldoximes Ketoximes and Amidoximesmentioning

confidence: 99%