7-Methyl-4-phenyl-8H-1,3,5,6-dithiadiazocin-2-on, ein achtgliedriger Heterocyclus mit chiraler Konformation

Ege, Günter

doi:10.1002/ange.19670791307

Cited by 7 publications

(1 citation statement)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cyclocondensation of 1-aminopyrimidine-2-thione with the WiUsmeier reagent (HCONMe2-POC13) gave the salts XLVII (R = H) [76]. Compounds XLIX, L, and XLVI can also be obtained by heating N-acylamino-~x-mercapto derivatives of imidazoles [3], thiazoles [77] and 1,2,4-triazoles [35,78,79] with POCI 3 or conc. The 1-aminopyridinium salt LIV reacts with acyl chlorides to give the acylation products LV which are converted into the oxazolo[3,2-a]pyridines LVI apparently by nucleophilic displacement of the SMe group by the carbonyl oxygen atom [81]:…”

Section: Reactions With Carboxylic Acids and Their Derivativesmentioning

confidence: 99%

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

Dyablo¹,

Пожарский²

1997

Chem Heterocycl Compd

View full text Add to dashboard Cite

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.

show abstract

Section: Reactions With Carboxylic Acids and Their Derivativesmentioning

confidence: 99%

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

Dyablo¹,

Пожарский²

1997

Chem Heterocycl Compd

View full text Add to dashboard Cite

show abstract

Ein optisch aktives Heteroocin

Ege

Planer

1969

Angewandte Chemie

View full text Add to dashboard Cite

Das IH-NMR-Spektrum von 7-Methyl-4-phenyl-8H-1,3,5,6dithiadiazocin-2-on (5a) zeigte fur die Methylenprotonen ein AB-Spektrum, woraus auf eine chirale Konforrnation geschlossen wurde "1. Das Ausbleiben einer Koaleszenz der Signale bis 150 OC liefl die Trennbarkeit in optische Antipoden vermuten. Die optische Spaltung gelang mit dem Carboxyderivat (56). Achttagiges Kochen von Terephthalsiluredimethylester und Hydrazinhydrat im Molverhiiltnis 2:l in Dioxan fuhrte zum

show abstract

An Optically Active Heteroocine

Ege

Planer

1969

Angew. Chem. Int. Ed. Engl.

View full text Add to dashboard Cite

7-Methyl-4-phenyl-8H-1,3,5,6-dithiadiazocin-2-on, ein achtgliedriger Heterocyclus mit chiraler Konformation

Abstract: Bei Behandlung rnit 2 N NaOH addiert die Verbindung (3a) ein Hydroxid-Anion an die Imonium-Doppelbindung. Die entstehende Hydroxyverbindung (4) wird jedoch sofort Reduktions-MittelAusb. (%)

Cited by 7 publications

References 3 publications

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

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

Ein optisch aktives Heteroocin

An Optically Active Heteroocine

Contact Info

Product

Resources

About