Rearrangements of Some Benzoylvinylisothiourea and of Metathiazine Derivatives

Cavallito, Chester J.; Martini, Catherine M.; Nachod, Frederick C.

doi:10.1021/ja01150a038

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Rsc(=nh)nh2 • Hc1 [Rsc(=nh)nh8]+c1-[rsc(=nh2)nh2]+cr1

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1955

1994

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Cited by 14 publications

(2 citation statements)

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“…CHsSH + (C2H6)2XCX -j^r^( C2H6)2XC(SCH3)=XH It has also been observed that the sulfur of a 1,3-disubstituted thiourea will add to an acetylenic bond to give a pseudothiourea salt in acid medium (40).…”

Section: Rsc(=nh)nh2 • Hc1 [Rsc(=nh)nh8]+c1-[rsc(=nh2)nh2]+crmentioning

confidence: 99%

Thioureas

Schroeder¹

1955

Chem. Rev.

196

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Section: Rsc(=nh)nh2 • Hc1 [Rsc(=nh)nh8]+c1-[rsc(=nh2)nh2]+crmentioning

confidence: 99%

Thioureas

Schroeder¹

1955

Chem. Rev.

196

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“…Die laut Lit. [14] leicht eintretende Umlagerung von 2-Amino-4-phenyl-l,3-thiazinium-chlorid (11, X=C1) zu 4-Phenyl-p:yrimidin-2-thion (18) ist indes schwerlich zu reproduzieren. Soweit von uns konstatiert, wird sie, zumal bei X = ClO,, in Triethylamin/Acetonitril und in KaliumcarbonatIEthanol, im erheblichen Mafle von Nebenreaktionen zu einer Serie vorerst nicht definierter Produkte begleitet.…”

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Zur Existenzfähigkeit von 2‐Imino‐2H‐1,3‐thiazinen

et al. 1990

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On the Existence of 2‐Imino‐2H‐1,3‐thiazines The title compounds 2 are readily liberated from the 2‐amino‐1,3‐thiazinium salts 1 by treatment with bases. Their stability depends sensitively on the substituents at the imino‐N. The imino‐N substituted 2a–i are isolable as well‐defined coloured substances. Reaction of the 2 as well 1 with nucleophilic agents affords pyrimidine‐2‐thiones (4, 9–11, 16–18). In these ring transformations a nucleophilic addition at ring position 6 as primary reaction step is preferred. The imino‐N unsubstituted representatives display a more complicated behaviour; the highly enhanced reactivity prevents or handicaps, respectively, any isolation. As exemplified in the base‐induced ring‐transformation of 1 m to the pyrimidine derivative 19, these 2 are able to react as nucleophiles too, and versatile intermolecular self‐reactions are increasingly favoured.

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1962

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Rearrangements of Some Benzoylvinylisothiourea and of Metathiazine Derivatives

Cited by 14 publications

References 0 publications

Thioureas

Thioureas

Zur Existenzfähigkeit von 2‐Imino‐2H‐1,3‐thiazinen

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