Parallel synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives on traceless solid support |
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Authors: | Suyoun Lee Doohyun Lee Kyung-Sik Song Kwang-Hyeon Liu Young-Dae Gong Taeho Lee |
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Institution: | 1. College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, Republic of Korea;2. Center for Innovative Drug Library Research, Department of Chemistry, College of Natural Science, Dongguk University-Seoul, 26 Pildong 3-ga, Jung-gu, Seoul 100-715, Republic of Korea |
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Abstract: | A parallel solid-phase synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives was developed. The polymer-supported synthetic route progressed using the sulfide linker via a traceless strategy. The initial synthesis utilized the Thorpe–Ziegler type cyclization of α-haloketone and polymer-supported 2,2-dicyanoethene-1,1-bis(thiolate), which was derived from the Merrifield resin. The resulting thiophene resin was introduced to one substitution by N-arylation. After oxidation of sulfides to sulfones in the thiophene resins for subsequent cleavage, nucleophilic desulfonative substitution with amines and thiols afforded the desired thiophene-3-carbonitrile derivatives in good overall yields. |
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Keywords: | Thiophene-3-carbonitrile Solid-phase synthesis Combinatorial chemistry Heterocycles |
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