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  • 1985-1989  (8)
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  • 1
    Electronic Resource
    Electronic Resource
    1,4-Dithiafulvene aus der Umsetzung von 4,4-disubstituierten 1,3-Thiazol-5(4H)-thionen mit AcetylenderivatenVorläufige Mitteilung s. [1]. (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 419-429 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,4-Dithiafulvenes, Products of the Reaction of 4,4-Disubstituted 1,3-Thiazol-5(4H)-thiones and Acetylenic CompoundsOn heating in toluene, 4,4-disubstituted 1,3-thiazol-5(4H)-thiones 1 and acetylenecarboxylates or acetylenecarbonitriles 2 undergo a cyclosubstitution reaction to yield 2-methylidene-1,3-dithiol derivatives 3 (1,4-dithiafulvenes) and a nitrile. Further heating of 3a and 3b in the presence of excess 2a leads to the isomeric 2,3-dihydrothiophene-2-thiones 4a and 4b, respectively. The benzodithiafulvene 14 has been formed in a similar reaction from 1a and in situ generate benzyne.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690223
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  • 2
    Electronic Resource
    Electronic Resource
    Carbophile Additionen von Organocupraten mit 1,3-Thiazol-5(4H)-thionen (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 1837-1843 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Carbophilic Additions of Organocuprates and 1,3-Thiazole-5(4H)-thionesOrganocuprates and 1,3-thiazole-5(4H)-thiones 1 react in THF at 0° via carbophilic addition onto the C—S bond to give 4,5-dihydro-1,3-thiazole-5-thiols 3 (Scheme 3). This observation is in marked contrast to the previously described reaction of organolithium compounds and 1, which undergo a thiophilic addition onto the exocyclic S-atom. As an exception, treatment of the 1,3-thiazole-5(4H)-thione 1a with tert-butyl cuprate leads to 7a (Scheme 3).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690809
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  • 3
    Electronic Resource
    Electronic Resource
    Bildung von 5,6-Dihydro-1,3(4H)-thiazin-4-carbonsäure-estern aus 4-Allyl-1,3-thiazol-5(4H)-onen (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 1639-1646 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Formation of Methyl 5,6-Dihydro-l, 3(4H)-thiazine-4-carboxyiates from 4-Allyl-l, 3-thiazol-5(4H)-ones.The reaction of N-[1-(N, N-dimethylthiocarbamoyl)-1-methyl-3-butenyl]benzamid (1) with HCl or TsOH in MeCN or toluene yields a mixture of 4-allyl-4-methyl-2-phenyl-1,3-thiazol-5(4H)-one (5a) and allyl 4-methyl-2-phenyl-1,3-thiazol-2-yl sulfide (11; Scheme 3). Most probably, the corresponding 1,3-oxazol-5(4H)-thiones B are intermediates in this reaction. With HCl in MeOH, 1 is transformed into methyl 5,6-dihydro-4,6-dimethyl-2-phenyl-1,3(4H)-thiazine-4-carboxylate (12a). The same product 12a is formed on treatment of the 1,3-thiazol-5(4H)-one 5a with HCl in MeOH (Scheme 4). It is shown that the latter reaction type is common for 4-allyl-substituted 1,3-thiazol-5(4H)-ones.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720724
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  • 4
    Electronic Resource
    Electronic Resource
    2,4-Bis(4-methylpheylthio)-1,3,2λ5,4λ5-dithiadiphosphetan-2,4-dithion: Ein neues Reagens zur Schwefelung von N,N-disubstituierten Amiden (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 1001-1011 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,4-Bis(4-methylphenylthio)-1,3,2λ5,4λ5-dithiadiphosphetane-2,4-dithione: A New Reagent for Thiation of N,N-Disubstituted AmidesAs a new reagent for the thiation of amides, the easily accessible 2,4-bis(4-methylphenylthio)-1,3,2λ5,4λ5-dithiadiphosphetane-2,4-dithione (9) shows a remarkable selectivity. This selectivity - the preferred thiation of N,N-disubstituted amides - is complementary to the one of the well known Lawesson reagent. Thiation of diamides of type 2 with 9 leads via cyclization of the corresponding dithiodiamides to 1,3-thiazole-5(4H)-thiones 1 (Scheme 3).
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19870700412
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  • 5
    Electronic Resource
    Electronic Resource
    Umsetzungen von 1,3-Thiazol-5(4H)-thionen mit Grignard- und Organolithium-Verbindungen: Carbophile und Thiophile Additionen (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 773-785 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of 1,3-Thiazole-5(4H)-thiones with Grignard- and Organolithium Compounds: Carbophilic and Thiophilic AdditionsOrganolithium compounds and 1,3-thiazole-5(4H)-thiones 9 reacted via thiophilic addition on the exocyclic S-atom. The intermediate anion E has been trapped by protonation to give 12 and by alkylation to yield 16, respectively (Schemes 5 and 6). In competition with protonation of E, a fragmentation to benzonitrile and a dithioester 14 was observed (Scheme 5). In some cases, the alkylation of E led to the formation of dithioacetals 17 instead of 16 (Scheme 6). Methyl, ethyl, and isopropyl Grignard reagents and 9 in THF underwent again a thiophilic addition yielding 4,5-dihydro-1,3-thiazoles of type 12 (Scheme 3). In contrast to this result, MeMgI reacted with 9a in Et2O via carbophilic addition to 11. Again a carbophilic attack at C(5) of 9 was observed with allylmagnesium and 2-propynylmagnesium bromide, respectively, in Et2O.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690404
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  • 6
    Electronic Resource
    Electronic Resource
    Additionsreaktion von 1,3-Thiazol-5(4H)-thionen und inaminen; Bildung von Thioamiden und ThioketonenAuszugsweise präsentiert am ‘Eleventh Symposium on the Organic Chemistry of Sulfur’ in Lindau/BRD, September 1984. (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 174-183 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Addition Reaction of 1,3-Thiazole-5(4H)-thiones and Ynamines; Formation of Thioamides and ThioketonesYnamines and 1,3-thiazole-5(4H)-thiones of type 1 undergo an addition reaction on heating in toluene yielding mainly α,β-unsaturated 2-(4,5-dihydro-1,3-thiazol-5-yliden)thioamides of type 7 (Scheme 2 and Table). In some cases, 1-diethylamino-1-(4,5-dihydro-1,3-thiazol-5-yliden)-2-alkanethiones 8 have been isolated as minor products. In analogy to other reactions of ynamines with C=O and C=S bonds, a [2 + 2] cycloaddition to thiete intermediates, followed by an electrocyclic ring opening is suggested as reaction mechanism.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690121
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  • 7
    Electronic Resource
    Electronic Resource
    Synthese von (Methylthio)penam-Derivaten durch Keten-Addition an 4,5-Dihydro-5-(methylthio)-1,3-thiazole (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 1424-1434 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of (Methylthio)penam Derivatives via Keten Addition onto 4,5-Dihydro-5-(methylthio)-1,3-thiazolesThe 4,5-dihydro-5-(methylthio)-2-phenyl-1,3-thiazoles 3a and 3b, easily prepared from the corresponding 1,3-thiazol-5(4H)-thiones and MeLi, react with dichloroacetyl chloride (5a) and acidoacetyl chloride (5b) in the presence of Et3N to give (methylthio)penam derivatives 6 (Table 1). The reaction mechanism is either a [2 + 2] cycloaddition of in situ generated ketene or a two-step reaction (Scheme 2). The structure of 6f has been confirmed by X-ray crystallography (Fig. 2). The relative configuration of 6a-e follow from comparison of their 1H-NMR spectra with those of 6f (Fig. 1). The 6-azidopenams 6d and 6f have been reduced to aminopenams 8a and 8b, respectively. Acylation of 8a with phenacetyl chloride yields 9 (Scheme 4).
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690615
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  • 8
    Electronic Resource
    Electronic Resource
    Radikalische Cyclisierungen von Alkenyl-substituierten 4,5-Dihydro-1,3-thiazol-5-thiolenVorgetragen (H. H.) am ‘11th International Congress of Heterocyclic Chemistry’, Heidelberg, 16-21. August 1987. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 838-846 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Radical Cyclizations of Alkenyl-Substituted 4,5-Dihydro-1,3-thiazole-5-thiolsHeating of 5-alkenyl- or 5-alkinyl-4,5-dihydro-1,3-thiazole-5-thiols of type 5 in the presence of a radical initiator gave dithiaspirobicycles in fair-to-excellent yield (Scheme 3). Under analogous conditions, the 4,5-dihydro-4-vinyl-1,3-thiazole-5-thiol 5d underwent a cyclization to give the annellated dithiabicycle 7 (Scheme 4). In this reaction, a minor product 8 was formed by an unknown reaction mechanism. The structure of 8 was established by X-ray crystallography. The starting 1,3-thiazole-5-thiols 5 have been synthesized by carbophilic alkylation of me C=S group of 1,3-thiazole-5(4H)-thiones with Grignard-reagents or alkylcuprates. The thiazolethiones were obtained by the reaction of 3-amino-2H-azirines with thiobenzoic acid followed by sulfurization and cyclization. The 4-benzyl derivative 1b was thermally rearranged via 1,3-benzyl migration to yield the benzyl (1,3-thiazol-5-yl) sulfide 11 (Scheme 5).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720425
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