Synthesis of substituted thiazolo[4,5-b]pyridines and other annulated heterocycles via SN2→Thorpe-Ziegler→Thorpe-Guareschi domino reactions |
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Authors: | Anatoliy M Shestopalov Liudmila A Rodinovskaya Alexander A Shestopalov |
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Institution: | N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russian Federation |
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Abstract: | A new combinatorial method for the preparation of substituted thiazolo4,5-b]pyridines, which utilizes cyanoacetamide, heterocumulenes (isothiocyanates, carbon bisulfide), and ethyl-4-chloroacetoacetate in a new SN2→Thorpe-Ziegler→Thorpe-Guareschi domino reactions has been developed. The obtained thiazolo4,5-b]pyridines were then used together with aldehydes and malononitrile in another Knoevenagel reaction→Michael reaction→hetero-Thorpe-Ziegler domino reaction for the synthesis of substituted 4,6-dihydro-5H-pyrano2,3-d]thiazolo4,5-b]pyridines. |
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Keywords: | Domino reactions Ethyl-4-chloroacetoacetate Thiazolo[4 5-b]pyridines 5H-Pyrano[2 3-d]thiazolo[4 5-b]pyridines |
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