- Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5-a]quinolines
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An efficient and rapid synthetic approach for the synthesis of tetrazolo[1,5-a]quinolines has been developed employing the reaction of o-alkynylisocyanobenzenes with sodium azide. The present strategy involved nucleophilic addition of azide to isocyanide followed by 6-endo cyclization. The reaction gives access to a collection of tetrazolo[1,5-a]quinolines with broad functional group in moderate to high yields under metal-, and base-free conditions.
- Khaikate, Onnicha,Soorukram, Darunee,Leowanawat, Pawaret,Pohmakotr, Manat,Reutrakul, Vichai,Kuhakarn, Chutima
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p. 7050 - 7057
(2019/11/11)
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- An elegant synthesis of indoloquinoline alkaloid cryptotackieine via Vilsmeier-Haack approach
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An exclusive approach towards the synthesis of indoloquinoline alkaloid cryptotackiene has been illustrated. Primary starting materials with an established procedure like Vilsmeier-Haack cyclization are used followed by nucleophilic azidation, intra-molecular cyclization and a selective methylation to achieve the target.
- Pitchai,Sathiyaseelan,Nepolraj,Gengan
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p. 1290 - 1292
(2015/11/25)
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- Synthesis of quinolinones with palladium-catalyzed oxidative annulation between acrylamides and arynes
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An unprecedented palladium-catalyzed oxidative annulation of acrylamides with benzyne precursors has been successfully developed. By using this mild "N-H activation/Heck reaction" method, a wide variety of quinolinones were conveniently prepared in one st
- Wang, Weiguo,Peng, Xianglong,Qin, Xiaoyu,Zhao, Xiangyun,Ma, Chen,Tung, Chen-Ho,Xu, Zhenghu
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p. 2835 - 2841
(2015/03/18)
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- Synthesis of 2-halogenated quinolines by halide-mediated intramolecular cyclization of o-alkynylaryl isocyanides
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When o-alkynylaryl isocyanides 1 are treated with triethylamine in chloroform, intramolecular chlorinating cyclization of the isocyanides takes place, affording the corresponding 2-chlorinated quinoline derivatives 2 in good to excellent yields, selective
- Mitamura, Takenori,Nomoto, Akihiro,Sonoda, Motohiro,Ogawa, Akiya
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supporting information; experimental part
p. 822 - 824
(2010/09/06)
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- Tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes: an efficient synthesis of 2-chloro-3-substituted quinolines
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A highly efficient one-pot synthesis of 2-chloro-3-substituted quinolines has been developed by tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes, which are generated in situ by dehydration of the corresponding N-(2-eth
- Liu, Lanying,Wang, Yong,Wang, Honggen,Peng, Changlan,Zhao, Jiaji,Zhu, Qiang
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body text
p. 6715 - 6719
(2010/01/18)
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- Synthesis of 4-Aryl-2-aminopyridine derivatives and related compounds
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A short, efficient, and high-yielding synthesis of 4-aryl-2-aminopyridine derivatives has been developed. The route employs two palladium-catalyzed processes, the Suzuki reaction and the Buchwald-Hartwig amination, as the key steps. The same approach has
- Pavlovic, Vladimir,Petkovic, Milos,Popovic, Stanimir,Savic, Vladimir
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experimental part
p. 4249 - 4263
(2010/01/15)
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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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- Carbostyril derivatives used as coccidiostats
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Carbostyril derivatives useful as coccidiostats are prepared by reacting an ortho-halo benzaldehyde with a 2-alkyl-2-oxazoline, then heating at above about 200° C thereby forming the carbostyril.
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