New regio-selective method of combinatorial synthesis of substituted thiophenes,thieno[3,2-b]pyridines and other heterocycles via combination of ‘domino’-type reactions |
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Authors: | Andrey A Zubarev Anatoliy M Shestopalov Natalia A Larionova Lyudmila A Rodinovskaya Alexander A Shestopalov |
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Institution: | N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation |
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Abstract: | We present a novel combinatorial multicomponent regio-selective approach towards the synthesis of thieno3,2-b]pyridines and pyridine pyrans. The methodology is based on the ‘domino’-type reaction. The high regio-selectivity in this reaction is gained by the in situ generation of the mono-potassium salt of 2-cyano-1-mercaptoethenethiolate. We also demonstrate that the use of ethyl 2-cyanoacetate in this reaction as a CH-acid leads to the termination of the domino sequence at the Dieckmann condensation step and yields novel ethyl 3-(4-cyano-3-hydroxy-5-(alkylthio)thiophen-2-yl)-3-oxopropanoate. |
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Keywords: | Domino reactions Multicomponent reactions Thieno[3 2-b]pyridines Combination of reaction types 2-Amino-4H-pyrans |
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