Parallel synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives on traceless solid support
2014
Lee, Suyoun | Lee, Doohyun | Song, Kyung-Sik | Liu, Kwang-Hyeon | Gong, Young-Dae | Lee, Taeho
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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