1094615-29-8Relevant academic research and scientific papers
Parallel synthesis of a desketoraloxifene analogue library via iodocyclization/palladium-catalyzed coupling
Cho, Chul-Hee,Jung, Dai-Il,Neuenswander, Benjamin,Larock, Richard C.
, p. 501 - 510 (2011/10/31)
For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen-bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions to give multimethoxy-substituted desketoraloxifene analogues 6. Various hydroxyl-substituted desketoraloxifene analogues 7 were subsequently generated by demethylation with BBr3.
Competition studies in alkyne electrophilic cyclization reactions
Mehta, Saurabh,Waldo, Jesse P.,Larock, Richard C.
supporting information; experimental part, p. 1141 - 1147 (2009/07/11)
The relative reactivity of various functional groups toward alkyne electrophilic cyclization reactions has been studied. The required diarylalkynes have been prepared by consecutive Sonogashira reactions of appropriately substituted aryl halides and competitive cyclizations have been performed using I2, ICl, NBS and PhSeCl as electrophiles. The results indicate that the nucleophilicity of the competing functional groups, polarization of the alkyne triple bond, and the cationic nature of the intermediate are the most important factors in determining the outcome of these reactions.
