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Updated: May 30, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Efficient synthesis and reactions of 1,2-dipyrrolylethynes
Hillary K Tanui1, Erhong Hao, Moses I Ihachi
1Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
Abstract:
Various dipyrroles possess important motifs for construction of pyrrole-containing pigments. A series of 1,2-dipyrrolylethynes (4a-d) has been efficiently synthesized using an improved one-pot double Sonagashira coupling from trimethylsilylethyne and various 2-iodopyrroles. The resulting 1,2-dipyrrolylethynes were further transformed into novel indolyl-, ethenyl- and carboranyl-dipyrroles (5-7) using the Larock indole synthesis, stereoselective catalytic hydrogenation, or B(10)H(14). Indolyl-dipyrroles were found to selectively bind fluoride ions using one pyrrolic and the indolyl NHs, whereas the carboranyl- and ethenyl-dipyrroles are potentially valuable precursors for the synthesis of porphyrin isomers and expanded pigments.
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