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Synthesis of Tetrasubstituted Thieno[3,2‐ b ]pyridin‐5(4 H )‐one Derivatives as a Heterocyclic Scaffold for Multisite‐specific Fluorous Fluorescent Tagging and Fluorous Solid‐Phase Extraction
Author(s) -
Jeon MoonKook,
Yi SuJin,
Son Seung Uk
Publication year - 2016
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.10840
Subject(s) - chemistry , fluorescence , combinatorial chemistry , alkoxy group , solid phase extraction , solid phase synthesis , extraction (chemistry) , scaffold , organic chemistry , peptide , biochemistry , medicine , physics , quantum mechanics , biomedical engineering , alkyl
Tetrasubstituted thieno[3,2‐ b ]pyridin‐5(4 H )‐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(4 H )‐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.