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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 125 (1994), S. 1129-1143 
    ISSN: 1434-4475
    Keywords: Pyrimidine-5-thioles ; Thiazolidine-2,4-diones ; Thiazoline-2-ones ; Thiazoline-2-thiones ; Thiazolo[4,5-e]isothiazoles ; Thiazolo[4,5-d]pyrimidines
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary 6-Amino-thiazolo[4,5-c]isothiazole derivatives4 are obtained by addition of hydrogen sulfide to the 4-Amino-thiazoline-5-carbonitrile2 followed by cyclooxidation of the intermediate thioamides3. In the presence of sodium sulfite the hydrolysis of the4-amino-2-methylthio-thiazolium salts5 derived from the title compounds1 yields the4-amino-thiazolin-2-ones6. By their further hydrolysis the 2,4-dioxo-thiazolidin-5-carboxamides8 are formed. The 2-oxo-and 2-thioxo-thiazolo [4,5-d]pyrimidin-7-ones and -thiones available from1 undergo ring opening by hydrolysis to give the substituted 4-amino-6-oxo- and 4-amino-6-thioxo-pyrimidine-5-thiols15a–h and13i–e. They have been isolated as their disulfides14 or 5-alkyl derivativesi.e. the substituted 4-amino-5-alkylthiopyrimidin-6-ones and -thiones16. In analogy, the intermediate 6-amino-7-oxo-thiazolo[4,5-d] pyrimidin-2-thione18 and the 7-amino-thiazolo[4,5-d]-pyrimidin-2-thione24 derived from1 react by ring cleveage to yield the 1,4-and 4,6-diamino-pyrimidin-5-thiole derivatives22 and27, respectively, isolated as their disulfides or alkylthio-derivatives. From the pyrimidine16b the pyrimido[5,4-b]1,4-thiazine derivative18 can be obtained.
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  • 2
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 334 (1992), S. 89-91 
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Simple Synthesis of 2,3-Diamino-quinoline-3-carbonitriles
    Additional Material: 2 Tab.
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  • 3
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 334 (1992), S. 491-496 
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On the Synthesis of 3-Amino-pyrroles by Thorpe-Ziegler-CyclizationN-Aryl and alkylaminomethylene cyanacetic acid derivatives 1 react with α-halogencarbonyl compounds 2 in the presence of potassium carbonate/sodium ethoxide to yield the substituted 3-amino-pyrroles 6. Using the same principle of cyclization pyrrole derivatives 6 can also be obtained by reaction of β-chloro- and β-alkoxymethylenemalononitriles 4 with β-aminocarbonyl compounds 5. From the malononitrile derivatives 1 containing the methylthio group in the β-position, and α-halogen ketones 7, the 2-dicyanomethylene oxazolines 8 arise which undergo alkoholysis by treatment with sodium alkoxide to form the 3-amino-5-alkoxy-pyrrole derivatives 9.
    Additional Material: 3 Tab.
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  • 4
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 322 (1980), S. 1021-1031 
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Substituted 4-Amino-thieno[2,3-c]isothiazoles and 4-Amino-thieno[3,2-d]isothiazolesThe alkylation of disodium-(4-cyanisothiazole-3,5)-dithiolate 1 with α-chloro carbonyl compounds followed by THORPE-ZIEGLER-cyclization yields the substituted 4-amino-thieno[3,2-d]isothiazoles 3, which can be converted into the thieno-isothiazolo-1,4-thiazepine derivatives 4, 5. The successive alkylation of 1 with dimethylsulfate and α-chloro carbonyl compounds yields the 5-methylthio-isothiazole-4-carbonitriles 11 which are cyclized to form the substituted 4-amino-3-methylthio-thieno[3,2-d]isothiazoles 13. The inverse alkylation procedure leads to the isomeric 4-amino-3-methylthio-thieno[2,3-c]isothiazoles 20. Successive alkylation of the 3-hydroxy-5-mercapto-4-cyanoisothiazoles 14 with α-chloro carbonyl compounds and diazomethane followed by cyclization yields the 4-amino-3-methoxy-thieno[3,2-d]isothiazoles 17. From 13 and 20 the isothiazole-thieno-pyrimidines 21, 22 and the isothiazolo-thieno-oxazinone 25 are synthesized.
    Additional Material: 7 Tab.
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  • 5
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 328 (1986), S. 459-464 
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Substituted 3,4-Diamino-thieno[2,3-b]pyrroles
    Additional Material: 2 Tab.
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  • 6
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 316 (1974), S. 299-303 
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bei der gemeinsamen Einwirkung von aromatischen Aldehyden und Schwefel auf α-Aminobenzylcyanid entstehen 5-Arylidenamino-2-aryl-4-phenylthiazole 1, aus denen durch hydrolytische Spaltung die freien 5-Amino-2-aryl-4-phenyl-thiazole 2 erhalten werden.
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  • 7
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 317 (1975), S. 329-334 
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: α-Arylhydrazono-thioamide 1  -  erhältlich aus Arylhydrazono-cyanessigsäurederivaten und Schwefelwasserstoff  -  werden mit Brom zu 5-Amino-2-aryl-1,2,3-thiadiazoliumsalzen 2 oxydiert. Die Verbindungen sind acylierbar und reagieren mit Acetessigester sowie methylenaktiven Nitrilen unter Spaltung der N-S-Bindung und erneuter Cyclisierung zu substituierten 4-Aminothiazolen 4,5. Dagegen führt die Behandlung mit anderen Basen zur Entschwefelung und Rückbildung des α-Arylhydrazono-nitrils.
    Additional Material: 3 Tab.
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  • 8
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 328 (1986), S. 741-749 
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On the Chemistry of 5-Amino-2-phenyl-1,2,3-thiadiazolium SaltsTreatment of the title compounds 1 with pyridine yield the phenylhydrazones of the 1,2,4-thiadiazol-3,5-diyl-glyoxylic acid derivatives 4. The amides 4a, b can also be obtained by reaction of the phenylhydrazono cyanacetoamides 3a, b with sulphur in the presence of pyridine. Nitriles react with 1 to form the phenylhydrazones of the 1,2,4-thiadiazol-5-yl-glyoxylic acid derivatives 6. Reduction of 6a yields the 1,2,4-thiadiazol-5-yl-glycine derivative 7. Depending on its condition the reaction of 1c with benzoyl acetonitrile yield either the 1,2,4-thiadiazole or the 4-amino-thiazole derivative (6i or 8). From 1a and ethyl acetoacetate the phenylhydrazone of the thiazol-2-yl-glyoxylic acid derivative 9 arises which can be reduced to yield the thiazol-2-yl-glycine derivative 10. The addition of 1 onto isothiocyanates in the presence of pyridine yields the substituted N-(1,2,3-thiadiazol-5-ylidene)-thioureas 12a, b. Carboxylic acids react with 1 in the presence of pyridine to form the 5-Acylimino-1,2,3-Δ3-thiadiazolines 13.
    Additional Material: 1 Tab.
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  • 9
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 330 (1988), S. 866-872 
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,3-Heterocondensed Thiophenes from Substituted 2-Aminothiophen-3-thioleEthyl 5-amino-4-mercapto-3-methyl-thiophen-2-carboxylate (2), obtainable from the appropriate thienylthiocyanate 1 by reduction, undergoes reactions in analogy to the 2-aminobenzenthiole. Thus, with formic acid or trimethylorthoacetat the thieno [2,3-d]thiazoles 4 and 5 are formed. Aromatic aldehydes yield the thieno[2,3-d]thiazolines (6) which can be dehydrogenated by sulphur to form 9. From carbon disulfide and 2 the thieno[2,3-d]thiazol-2-thione (7) is formed. With phenacylbromide or ethyl bromoacetate 2 can be converted into the thieno[3,2-b] thiazine derivatives 11 or 12. Diazotation of 2 yields the thieno[2,3-d]1,2,3-thiadiazole derivative (14).
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