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Iodide‐Catalyzed Phosphorothiolation of Heteroarenes Using P(O)H Compounds and Elemental Sulfur
Author(s) -
Shi Shanshan,
Chen Jun,
Zhuo Shaohua,
Wu Zi'ang,
Fang Meijuan,
Tang Guo,
Zhao Yufen
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900291
Subject(s) - chemistry , pyridine , catalysis , sulfur , indole test , iodide , combinatorial chemistry , medicinal chemistry , organic chemistry
Abstract Organothiophosphates have found widespread application as biologically active compounds and synthetic intermediates in medicinal chemistry. The first transition‐metal‐free one‐pot direct synthesis of heterocyclic phosphorothioates involving indole or imidazo[1,2‐a]pyridine derivatives, elemental sulfur, and P(O)H compounds is presented. The use of NaI or KI as a catalyst, tert ‐butyl hydroperoxide as an oxidant, various indole and imidazo[1,2‐a]pyridine derivatives are tolerant in this transformation, affording the corresponding products in good to excellent yields. Moreover, this method can be easily adapted to large‐scale preparation. O,O ‐Diethyl S ‐(1‐phenyl‐1H‐indol‐3‐yl) phosphorothioate presents potent anti‐inflammatory activity in lipopolysaccharide (LPS)‐stimulated RAW264.7 cells in a dose‐dependent manner.