Synthesis of Tetrasubstituted Thieno[3,2-b]pyridin-5(4H)-one Derivatives as a Heterocyclic Scaffold for Multisite-specific Fluorous Fluorescent Tagging and Fluorous Solid-Phase Extraction

• Published in: Bulletin of the Korean Chemical Society Vol. 37; no. 8; pp. 1204 - 1210
• Main Authors: Jeon, Moon-Kook, Yi, Su-Jin, Son, Seung Uk
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley-VCH Verlag GmbH & Co. KGaA 01.08.2016; Wiley‐VCH Verlag GmbH & Co. KGaA; 대한화학회
• Subjects: Fluorescence; Fluorous; Small molecule microarray; Solid-phase extraction; Tag; Thienopyridinone; 화학
• ISSN: 1229-5949; 0253-2964; 1229-5949
• DOI: 10.1002/bkcs.10840

Tetrasubstituted thieno[3,2‐b]pyridin‐5(4H)‐one derivatives were selected as a highly functionalized heterocyclic scaffold for a multisite‐specific tagging process utilizing a previously devised fluorous fluorescent tag system. A suitable synthetic method was established for the 7‐alkoxy‐2,4,6‐trisubstituted‐thieno[3,2‐b]pyridin‐5(4H)‐one derivatives, and incorporating t‐butoxycarbonyl‐functionalized building blocks into the reaction sequence produced precursors that could be used in the tagging process. Fluorous solid‐phase extraction facilitated the purification of the tagged target compounds after a series of reactions, including t‐Bu deprotection/N‐hydroxysuccinimidyl ester formation/amidation.