- Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis
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Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.
- Nicewicz, David A.,Pistritto, Vincent A.,Schutzbach-Horton, Megan E.
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supporting information
p. 17187 - 17194
(2020/11/02)
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- PHENYL AND PYRIDINYL HYDROXAMIC ACIDS
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The present invention relates to pyrimidine hydroxy amide compounds, the use of such compounds in the inhibition of HDAC6, and the use of such compounds in the treatment of various diseases, disorders, or conditions related to HDAC6.
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Paragraph 0133; 0134
(2018/05/24)
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- Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia
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A general and practical catalytic system for aryl amination of aryl chlorides with aqueous or gaseous ammonia has been developed, with CuI as the catalyst and bisaryl oxalic diamides as the ligands. The reaction proceeds at 105-120°C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.
- Fan, Mengyang,Zhou, Wei,Jiang, Yongwen,Ma, Dawei
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supporting information
p. 5934 - 5937
(2015/12/11)
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- Synthesis of the marine sponge derived β2-adrenoceptor agonist S1319
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(Chemical Equation Presented) The marine sponge derived β2-adrenoceptor agonist S1319 has been synthesized following a six-step linear sequence. Central to the approach employed is the formation of a 7-lithiated-2,4-dialkoxybenzothiazole interm
- Fairhurst, Robin A.,Janus, Diana,Lawrence, Annabel
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p. 4697 - 4700
(2007/10/03)
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- 2, 4- DI (PHENYLAMINO) PYRIMIDINES USEFUL IN THE TREATMENT OF NEOPLASTIC DISEASES, INFLAMMATORY AND IMMUNE SYSTEM DISORDERS
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Novel pyrimidine derivatives of formula (I), to processes for their production, their use as pharmaceuticals in the treatment of neoplastic diseases, inflammatory and immune system disorders and to pharmaceutical compositions comprising them.
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Page 138; 142
(2010/02/08)
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- 4,5,6,7-trisubstituted benzoxazolones
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Certain 6-aryl- or 6-heteroaryl- alkylaminobenzoxazolones, and their pharmaceutically-acceptable salts, are dual inhibitors of lipoxygenase and cyclooxygenase enzymes, and so are useful as antiallergy and antiinflammatory agents.
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- REGIOSPECIFIC SYNTHESIS OF CERTAIN 1,2,3,4-TETRASUBSTITUTED BENZENES IN ONE STEP VIA A BENZENE CYCLIZATION
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Tetrasubstituted benzenes of type 3 are obtained regiospecifically in a single step by the treatment of 1-fluoro-4-methoxy-5-carbo-tert-butoxy aniline with tert-butyllithium followed by reaction with an elecrophile.
- Fisher, Lawrence E.,Caroon, Joan M.
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p. 233 - 238
(2007/10/02)
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- ISOINDOLINYL-ALKYL-PIPERAZINES
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The invention is generally concerned with isoindolinyl-alkylpiperazine compounds generally characterized by the formula STR1 wherein X is halogen or trifluoromethyl; n is an integer ranging from 2 to 5; Y is STR2 in which R 1 is hydrogen, halogen, lower alkyl, lower alkoxy, trifluoromethyl, cyano; R 2 is hydrogen, halogen, lower alkyl, lower alkoxy; and R 3 is hydrogen, cyano. These compounds are useful as diuretic and/or antihypertensive agents.
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- Electrophilic Aromatic Substitution. Part 28. The Mechanism of Nitration of Some 4-Substituted Anisoles and Phenols, and of Rearrangement of the Intermediate 4-Nitro-4-substituted-cyclohexa-2,5-dienones
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The kinetics of nitration in sulphuric acid of 2-chloro-4-methyl-, 4-chloro-, 2,4-dichloro-, and 4-fluoroanisole and of the corresponding phenols have been determined.The reaction products from the anisoles and from 2-chloro-4-methyl- and 4-fluoro-phenol have been determined.Results for 4-methylanisole supplementary to earlier ones are also reported.Generally the anisoles give the 2-nitro-derivatives and the 2-nitrophenols, and from 2-chloro-4-methylanisole, 2-chloro-4-methyl-4-nitrocyclohexa-2,5-dienone was formed as an intermediate.The decomposition of this dienone in sulphuric acid, like those of others, changes from a non-acid-catalysed to an acid-catalysed form with increasing acidity.The first form is regarded as a decomposition into an aryloxyl radical and nitrogen dioxide which can recombine to give the 2-nitrophenol.The formation of a small amount of 2-(4-fluorophenoxy)-4-fluorophenol in the nitration of 4-fluorophenol is seen as support for this view.The acid-catalysed form is regarded as the decomposition of the protonated dienone into a phenol-nitronium ion encounter-pair which can give the nitrophenol.A consequence of the mechanism is that if the phenol were nitrated at less than the encounter rate, the phenol itself would in appropriate conditions be a product of the ipso-nitration of the original anisole. 4-Methyl-, 2-chloro-4-methyl-, and 4-chloro-phenol have been so identified.Quantitative analysis of the results allows evaluation of the partitioning of dienone decomposition between the two modes.The mechanism accounts for the formation from 2,4-dichloro-anisole of both 2,4-dichloro-6- and 2,4-dichloro-5-nitroanisole, but only 2,4-dichloro-6-nitrophenol.
- Bloomfield, Colin,Manglik, Ajay K.,Moodie, Roy B.,Schofield, Kenneth,Tobin, Geoffrey D.
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