- Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN
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A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.
- Qiao, Kai,Wan, Li,Sun, Xiaoning,Zhang, Kai,Zhu, Ning,Li, Xin,Guo, Kai
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p. 1606 - 1611
(2016/04/05)
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- Development of a facile and inexpensive route for the preparation of α-halobenzopyridines from α-unsubstituted benzopyridines
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A facile and inexpensive route for the preparation of α-halobenzopyridines from α-unsubstituted benzopyridines via N-methylbenzopyridin-α-ones was developed. α-Unsubstituted benzopyridines were converted easily into the corresponding N-methylbenzopyridin-α-ones, which were halogenated using PPh3-TCICA or PPh3-DBICA without using solvent to give α-halobenzopyridines.
- Sugimoto, Osamu,Iwasaki, Hyuma,Tanji, Ken-Ichi
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p. 1445 - 1454
(2015/07/15)
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- Fragment-Based Discovery of Low-Micromolar ATAD2 Bromodomain Inhibitors
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Overexpression of ATAD2 (ATPase family, AAA domain containing 2) has been linked to disease severity and progression in a wide range of cancers, and is implicated in the regulation of several drivers of cancer growth. Little is known of the dependence of
- Demont, Emmanuel H.,Chung, Chun-Wa,Furze, Rebecca C.,Grandi, Paola,Michon, Anne-Marie,Wellaway, Chris,Barrett, Nathalie,Bridges, Angela M.,Craggs, Peter D.,Diallo, Hawa,Dixon, David P.,Douault, Clement,Emmons, Amanda J.,Jones, Emma J.,Karamshi, Bhumika V.,Locke, Kelly,Mitchell, Darren J.,Mouzon, Bernadette H.,Prinjha, Rab K.,Roberts, Andy D.,Sheppard, Robert J.,Watson, Robert J.,Bamborough, Paul
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p. 5649 - 5673
(2015/08/03)
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- HETEROCYCLES FOR USE AS INHIBITORS OF LEUKOTRIENES
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The invention concerns a heterocycle of the formula I wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms; A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene; X is oxy, thio, sulphinyl, sulphonyl or imino; Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms; R 1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; and R 2 and R 3 together form a group of the formula --A 2 --X 2 --A 3 -- which, together with the carbon atom to which A 2 and A 3 are attached, defines a ring having 4 to 7 ring atoms, wherein A 2 and A 3, which may be the same or different, each is (1-4C)alkylene and X 2 is oxy, thio, sulphinyl, sulphonyl or imino; or a pharmaceutically-acceptable salt thereof. The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
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- REACTIONS OF 3-SUBSTITUTED QUINOLINE 1-OXIDES WITH ACYLATING AGENTS
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Reactions of 3-fluoro- (1a), 3-bromo- (1b), 3-methyl- (1c), 3-methoxy- (1d) and 3-acetamidoquinoline 1-oxides (1e) with acylating agents (POCl3, Ac2O, TsCl and PhCOCl) were examined (Table).While only 2-substituted quinolines were obtained from 1a and 1b, fair amounts of 4-substituted products were formed in reactions of 1d, the sole formation of the 4-acetoxyquinoline (6) with Ac2O being the most significant result. 2-Chloroquinolines, 4-chloroquinolines and 2-tosyloxyquinolines were formed (and sometimes predominate) in addition to 2-quinolinones in reactions with TsCl.
- Miura, Yutaka,Takaku, Sakae,Nawata, Yoshiharu,Hamana, Masatomo
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p. 1579 - 1586
(2007/10/02)
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- Synthesis and 5-Hydroxytryptamine Antagonist Activity of 2-thio>-3-phenylquinoline and Its Analogues
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A series of 2-quinolines substituted at the 3-position with alkyl, aryl, or heteroaryl groups has been prepared in the search for novel and selective 5-HT2 antagonists.The affinity of the compounds for 5-HT1 recep
- Blackburn, Thomas P.,Cox, Barry,Guildford, Allen J.,Count, David J. Le,Middlemiss, Derek N.,et al.
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p. 2252 - 2259
(2007/10/02)
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- A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 8. Conversion of Anilides into 3-Substituted Quinolines and into Quinoxalines
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Anilides (4) (ArNHCOCH2R) are readily converted into 2-chloro-3-R-quinolines (5) under Vilsmeier conditions and the 3-chloro-group may be removed with zinc and acetic acid yielding 3-substituted quinolines (7).When N-nitrosodialkylamines are used in place of dimethylformamide as the Vilsmeier agent, the anilides are converted into 2-chloroquinoxalines in low yields.Several by-products are formed and the mechanisms have been explored.Thus, the formation of ethyl N-arylcarbamate from the corresponding propionanilide is shown to involve an C->O alkyl migration related to a Wolff rearrangement, while N-arylformimidoyl dichloride (18), nitriles, and isocyanides are derived from C-C cleavage of the substituted side-chain.Variation of the acid chloride component of the Vilsmeier reagent or of the solvent was generally unproductive though use of phosphoryl bromide instead of the chloride caused conversion of anilides into bromoquinolines in low yields.
- Meth-Cohn, Otto,Rhouati, Salah,Tarnowski, Brian,Robinson, Andrew
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p. 1537 - 1543
(2007/10/02)
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