67856-45-5Relevant articles and documents
Umpolung Strategy for Arene C?H Etherification Leading to Functionalized Chromanes Enabled by I(III) N-Ligated Hypervalent Iodine Reagents
Mikhael, Myriam,Guo, Wentao,Tantillo, Dean J.,Wengryniuk, Sarah E.
, p. 4867 - 4875 (2021/09/14)
The direct formation of aryl C?O bonds via the intramolecular dehydrogenative coupling of a C?H bond and a pendant alcohol represents a powerful synthetic transformation. Herein, we report a method for intramolecular arene C?H etherification via an umpoled alcohol cyclization mediated by an I(III) N-HVI reagent. This approach provides access to functionalized chromane scaffolds from primary, secondary and tertiary alcohols via a cascade cyclization-iodonium salt formation, the latter providing a versatile functional handle for downstream derivatization. Computational studies support initial formation of an umpoled O-intermediate via I(III) ligand exchange, followed by competitive direct and spirocyclization/1,2-shift pathways. (Figure presented.).
An efficient preparation of chroman derivatives from 3-aryl-1-propanols and related compounds with 1,3-diiodo-5,5-dimethylhydantoin under irradiation conditions
Furuyama, Shusuke,Togo, Hideo
scheme or table, p. 2325 - 2329 (2010/11/16)
Treatment of various 3-aryl-1-propanols with 1,3-diiodo-5,5- dimethylhydantoin (DIH) in ethyl acetate or 1,2-dichloroethane under irradiation with a tungsten lamp gave the corresponding chroman derivatives in good to moderate yields. The present reaction proceeds via the initial formation of an alkoxyl radical and the radical cyclization onto the aromatic ring, followed by the oxidation of the formed radical intermediate with DIH to provide the chroman derivative. The same treatment of o-biphenyldimethylcarbinol, o-phenylbenzoic acid, and o-alkylbenzoic acids with DIH provided the corresponding chroman derivatives and lactone derivatives in good yields, respectively. Georg Thieme Verlag Stuttgart - New York.
INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
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Page/Page column 66-67, (2009/06/27)
Compounds of formula (I): wherein R4, R6 and R7 are defined herein, are useful as inhibitors of HIV replication.