Simple construction of fused and spiro nitrogen/sulfur containing heterocycles by addition of thioamides or thioureas on cycloalkenyl-diazenes: examples of click chemistry |
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Authors: | Orazio A Attanasi Gianfranco Favi Gianluca Giorgi Francesca R Perrulli |
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Institution: | a Istituto di Chimica Organica, Università degli Studi di Urbino ‘Carlo Bo’, Via I Maggetti 24, 61029 Urbino, Italy b Dipartimento di Chimica, Università degli Studi di Siena, Via Aldo Moro, 53100 Siena, Italy c Dipartimento di Chimica Organica ‘A. Mangini’, Università di Bologna, Via San Giacomo 11, 40126 Bologna, Italy |
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Abstract: | New 1-cycloalkenyl-1-diazenes have been obtained in good yields from cyclic β-ketoesters and hydrazine derivatives. They furnished new cycloalkyld]1,3]thiazolines with thioamides or new spirocycloalkyl-thiazolinones with thioureas. Moreover they gave, with imidazolidine-2-thione and tetrahydropyrimidine-2-thione, new and interesting spirocycloalkyl-1,2′-imidazo2,1-b]1,3]thiazole] or spirocycloalkyl-1,2′-1,3]thiazolo3,2-a]pyrimidine] derivatives, respectively. Cycloalkyld]1,3]thiazolines were useful for the further preparation of unknown thia-triaza-tricyclo derivatives. Novel hexahydro-1,3-benzothiazoles have been achieved by reaction of N,N′-dialkylthioureas on N-1-phenyl-2-(1-cyclohexenyl)-1-diazene-1-carboxyamide. The acidic hydrolysis of spirocycloalkyl-thiazolinones produced 2-imino-5-(ω-carboxyalkyl)-4-thiazolidinones. |
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