- Umpolung Strategy for Arene C?H Etherification Leading to Functionalized Chromanes Enabled by I(III) N-Ligated Hypervalent Iodine Reagents
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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.).
- Mikhael, Myriam,Guo, Wentao,Tantillo, Dean J.,Wengryniuk, Sarah E.
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supporting information
p. 4867 - 4875
(2021/09/14)
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- AZAINDOLE COMPOUNDS AND METHODS FOR TREATING HIV
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Provided are compounds and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the retrovirus family of viruses such as the Human Immunodeficiency Virus (HIV).
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- An efficient preparation of chroman derivatives from 3-aryl-1-propanols and related compounds with 1,3-diiodo-5,5-dimethylhydantoin under irradiation conditions
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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.
- Furuyama, Shusuke,Togo, Hideo
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scheme or table
p. 2325 - 2329
(2010/11/16)
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- INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
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Compounds of formula I : wherein c, R2, R3, R4, R5, R6, R7 and R8 are defined herein, are useful as inhibitors of HIV replication.
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- INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
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Compounds of formula (I): wherein R4, R6 and R7 are defined herein, are useful as inhibitors of HIV replication.
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Page/Page column 66-67
(2009/06/27)
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- INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
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Compounds of formula (I): wherein c, X, Y, R2, R4 and R5 are defined herein, are useful as inhibitors of HIV replication.
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Page/Page column 76
(2009/06/27)
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- INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
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The present invention relates to compounds of formula (I) wherein c, X, Y, R2, R3, R4 and R6 are as defined herein, compositions and uses thereof for treating human immunodeficiency virus (HIV) infection. In particular, the present invention provides novel inhibitors of HIV integrase, pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HIV infection
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Page/Page column 72-73
(2009/06/27)
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- Formation and synthetic use of oxygen-centred radicals with (diacetoxyiodo)arenes
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o-Alkyl- or o-aryl-benzenecarboxylic acids and alcohols containing an aromatic ring are treated with a (diacetoxyiodo)arene-iodine system to give the corresponding cyclized products such as phthalide, benzocoumarin and chromane derivatives in moderate to good yields via the corresponding oxygen-centred radicals. For the carboxylic acids, [bis(trifluoroacetoxy)iodo]benzene functions effectively, while (diacetoxyiodo)benzene is effective for the alcohols. Chromane and its derivatives are obtained as iodinated compounds by hypoiodite species derived from (diacetoxyiodo)benzene and iodine. Copyright 1997 by the Royal Society of Chemistry.
- Togo, Hideo,Muraki, Takahito,Hoshina, Yoichiro,Yamaguchi, Kentaro,Yokoyama, Masataka
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p. 787 - 793
(2007/10/03)
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- Remote functionalization: Cyclic alkoxylation onto aromatic ring via radical pathway
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Oxidative cyclization of alcohols containing an aromatic ring with (diacetoxyiodo)benzene and iodine gave the corresponding cyclic ethers via alkoxy radicals in good yields. The present method is very useful for the direct preparation of flavonoid and vitamin E analogues from the alcohols.
- Muraki,Togo,Yokoyama
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p. 2441 - 2444
(2007/10/03)
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