Synthesen stickstoffhaltiger Heterocyclen, XXXI. Über 1.2.4‐Triazine, V. Desaminierung von 4‐Amino‐1.2.4‐triazinen

Dornow, Alfred; Pietsch, Hanns; Marx, Paul

doi:10.1002/cber.19640970932

Cited by 21 publications

(1 citation statement)

References 6 publications

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“…For example, 4-amino-3-methylthio-l,3,4-triazines CXCIV reacted with hydroxylamine [155], dicarbodiimides [127,156], malonodinitrile [155], carbon disulfide [72,157] or underwent cyclodimerization [155]. The reaction of the aminothiones CXCV with hydrazine hydrate is an example of nucleophilic displacement of an unsubstituted mercapto group [158].…”

Section: Ph Phmentioning

confidence: 99%

Synthesis and properties of N-aminoazolinethiones and N-aminoazinethiones 2. Reactions

Dyablo¹,

Пожарский²

1997

Chem Heterocycl Compd

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Literature data on the reactivity of ct-mercapto derivatives of N-aminoazoles and N-aminoazines are reviewed.Data on the methods of synthesis of N-aminoazolinethiones and N-aminoazinethiones were systematically discussed in the first part of this review [1]. The sequel contains information on the chemical properties of these compounds, particularly pertaining to all types of heterocyclization involving the amino and mercapto groups. ELIMINATION OF N-AMINO AND MERCAPTO GROUPSThe basic method for the elimination of N-amino groups in heterocyclic aminothiones is treatment with nitrous acid. It is suggested that during these reactions, which usually occur with good yield, an unstable N-nitrosoamine of type I is formed, which decomposes with the evolution of nitrous oxide [2]. For example, the 1-aminoimidazoline-2-thiones II were converted into imidazolinethiones III In a number of cases oxidation of the mercapto group accompanied elimination of the amino group on treatment with nitrous acid. For example, 4-amino-l,2,4-triazoline-3,5-dithione (IV) was converted to the disulfide V in 95% yield [9]. The formation of similar disulfides was also observed for 3-aminothiazoline-2-thiones [10-12], 4-amino-5-anilino-l,2,4-triazoline-3-thiones [13] Rostov State University, Rostov-on-Don 344090.

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