Iron-Promoted Intramolecular Cascade Cyclization for the Synthesis of Selenophene-Fused, Quinoline-Based Heteroacenes

• Published in: Journal of organic chemistry Vol. 84; no. 13; pp. 8602 - 8614
• Main Authors: Sonawane, Amol D, Kubota, Yasuhiro, Koketsu, Mamoru
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.07.2019; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; ELECTROPHILIC CYCLIZATION; DIORGANYL DISELENIDES SYNTHESIS; SOLAR-CELLS; IRON(III) CHLORIDE; HETEROCYCLES; OPTICAL-PROPERTIES; CHEMISTRY; ARYL; DICHALCOGENIDES; DERIVATIVES
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/acs.joc.9b01061

Herein, we report the Fe­(III)-promoted linear intramolecular cascade cyclization of 1,3-diyne and 1,3,5-triyne for the construction of selenophene-fused, quinoline-based heteroacene scaffolds. In one step, 1,3-diyne and 1,3,5-triyne were cyclized via diversified internal nucleophiles by using diorganyl diselenides. The diorganyl diselenide plays dual role, one as a cyclizing agent and second as insertion of one and/or two selenium atom and one R′-Se group in the final product. This is highly important in terms of atom economy. Diversified internal nucleophiles were used to afford quinoline- and acridine-based cores. The synthesized selenophene-fused derivatives showed λmax, F max, and Φf values in the range from 370–411 nm, 427–472 nm, and 0.003–0.059, respectively, in dichloromethane solvent.