2‐Bromo‐2‐chloro‐3‐arylpropanenitriles as C‐3 synthons for the synthesis of functionalized 3‐aminothiophenes

Batsyts, Sviatoslav; Shehedyn, Maksym; Goreshnik, Evgeny A.; Obushak, Mykola D.; Schmidt, Andreas GND; Ostapiuk, Yurii V.

2-Bromo-2-chloro-3-arylpropanenitriles can be prepared by Meerwein reaction from 2-chloroacrylonitrile and various aryldiazonium salts under copper(II) bromide catalysis. They proved to be stable compounds which form 2-chlorocinnnamonitriles upon treatment with bases. Reaction of the title compounds with substituted thioglycolates gave substituted 3-aminothiophenes which have not yet been accessible by other routes. Three-component reactions with the title compound, sodium sulfide and bromonitromethane, chloroacetonitrile, or ethyl 4-chloroacetoacetate gave 2-nitro- and 2-cyano-substituted 3-aminothiophenes, and thienopyridinediones in high yields and in one single step, respectively.

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Batsyts, Sviatoslav / Shehedyn, Maksym / Goreshnik, Evgeny / et al: 2‐Bromo‐2‐chloro‐3‐arylpropanenitriles as C‐3 synthons for the synthesis of functionalized 3‐aminothiophenes. 2019.

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