Synthesis of C3-arylated-3-deazauridine derivatives with potent anti-HSV-1 activities

Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy

“…By comparision, our approach enabled a three‐step, one‐pot synthesis with overall 61 % yield via condensing 2‐pyrone ( 106 ) with benzylamine followed by Rh‐catalyzed α‐arylation with PhB(OH) 2 , highlighting the modularity and tunability of this strategy. Similarly, the synthesis of potent anti‐HSV‐1 agent 109 (Scheme 5b) required the intermediacy of 108 that was previously prepared in 4 steps with 30 % overall yield; [28] in contrast, our method enabled two‐step one‐pot access (85 % yield) without the use of protecting groups. The seemingly simple pontin ATPase inhibitor 7 (Scheme 5c) was previously synthesized through an elaborate eight‐step process involving excessive functional group manipulations and protecting group interchanges [2g] .…”

Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy

“…This CIY strategy allowed the introduction of a broad range of versatile synthetic handles, including ester (17), ketone (18), nitrile (19), phenol (25), aryl chloride (21 and 30), bromide (22 and 31), and even iodide (23) moieties. To our delight, a broad array of challenging ortho-substituted phenylboronic acids were competent coupling partners under our catalytic system and corresponding products (26)(27)(28)(29)(30)(31)(32)(33) were obtained in satisfying yields. Various heterocycles, such as quinoline (41), unprotected indole (42), and benzothiazole (43) could be conveniently coupled to 4-hydroxy 2-pyridone, indicating the potential of this strategy for rapid access to valuable biheteroaryls.…”

“…By comparision, our approach enabled a three-step, one-pot synthesis with overall 61 % yield via condensing 2-pyrone (106) with benzylamine followed by Rh-catalyzed α-arylation with PhB(OH) 2 , highlighting the modularity and tunability of this strategy. Similarly, the synthesis of potent anti-HSV-1 agent 109 (Scheme 5b) required the intermediacy of 108 that was previously prepared in 4 steps with 30 % overall yield; [28] in contrast, our method enabled two-step one-pot access (85 % yield) without the use of protecting groups. The seemingly simple pontin ATPase inhibitor 7 (Scheme 5c) was previously synthesized through an elaborate eight-step process involving excessive functional group manipulations and protecting group interchanges.…”