Multicomponent Synthesis of Fluorescent Thiazole-Indole Hybrids and Thiazole-Based Novel Polymers

Herein, we report an efficient multicomponent reaction for the synthesis of trisubstituted thiazoles involving a one-pot C-C, C-N, and C-S bond-forming process from the readily available starting materials. The reaction of arylglyoxal, indole, and aryl thioamides in the acetic acid medium under sealed heating conditions provided 3-(2,4-diarylthiazol-5-yl)-1H-indoles (4) in good to excellent yields. Using a similar reaction strategy, the reaction of arylglyoxal, aryl thioamide, and 2,5-dihydroxy-1,4-benzoquinone provided structurally interesting bis-thiazoles having dihydroxy-1,4-benzoquinone linker (9). All of the products were fully characterized by spectroscopic techniques. We also recorded single-crystal X-ray diffraction (XRD) of compounds 4b and 9a for unambiguous structure determination. Indole-linked trisubstituted thiazoles (4) exhibit prominent fluorescence properties. The relative fluorescence quantum yields of all of the thiazole-linked indoles were measured in the dimethyl sulfoxide (DMSO) medium with respect to quinine sulfate in 0.1 M H2SO4 as reference. The scope of this reaction was further explored by preparing novel polymers 11a and 11b using naphthalene/benzene-1,4-bis(carbothioamide) in multicomponent polymerization.

Automated summary

Here, we present an efficient multicomponent reaction for the synthesis of trisubstituted thiazoles from readily available starting materials. The reaction yields good to excellent results and can also be used to synthesize structurally interesting bis-thiazoles. The structures of the products were confirmed through spectroscopic analysis and single-crystal X-ray diffraction. The indole-linked thiazole compounds produced by this method exhibit significant fluorescence properties. Furthermore, the scope of this reaction can be expanded to prepare novel polymers.