Trityl isothiocyanate support for solid-phase synthesis.
Trityl isothiocyanate resin [1], prepared from commercially available trityl chloride resin, is a useful precursor of the trityl thiosemicarbazide resin [2]. This resin can be employed in the solid-phase synthesis of a variety of supported isatin beta-thiosemicarbazones [4] and their Mannich derivatives [6]. A variety of thioureas [7] can be easily prepared by the reaction of [1] with amines. The supported thioureas are directly and efficiently converted to 2-aminothiazole-5-carboxylates [8] by reaction with methyl 2-chloroacetoacetate.
Pirrung
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Department of Chemistry, Levine Science Research Center, Duke University, Durham, North Carolina 27708-0317, USA.
Pansare
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D020650:Combinatorial Chemistry Techniques; D007510:Isatin / Q000737:chemistry*; D017879:Isothiocyanates; D009682:Magnetic Resonance Spectroscopy; D008352:Mannich Bases / Q000138:chemical synthesis*; D012116:Resins, Plant; D013844:Thiazoles / Q000138:chemical synthesis*; D013882:Thiosemicarbazones / Q000737:chemistry; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D017879:Isothiocyanates; D008352:Mannich Bases; D012116:Resins, Plant; D013844:Thiazoles; D013882:Thiosemicarbazones; D007510:Isatin; D013890:Thiourea