New 2-functionalized 2H-3,4-dihydro-1,4-benzothiazin-3-ones and their application in the synthesis of spiro heterocycles |
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Authors: | K.G. Nazarenko M.O. Lozinskii |
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Affiliation: | a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv, 02094, Ukraine b Research and Development Center for Chemistry and Biology, National Taras Shevchenko University, 62 Volodymyrska st., Kyiv, 01033, Ukraine |
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Abstract: | The reaction of 2-chloro-3,4-dihydro-2H-1,4-benzothiazin-3-ones 1 with enamines is an efficient synthetic method to produce 2-substituted derivatives. The resulting bifunctional compounds such as 6a,b, 7c,d and 8b react with hydrazines to furnish the spiro derivatives of N-aminopyrrole or 3-pyridazinone depending on the direction of the primary nucleophilic attack and the nature of the nucleophile. Under the reaction conditions, spiro pyridazinones 13 are converted into the 3-pyridazinone-4-carboxylic acid derivatives 9 via the 1,4-thiazine ring opening. |
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Keywords: | Chloro derivatives Enamines Electrophilic substitution Cyclization Spiro heterocycles |
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