Solvent-free synthesis of δ-carbolines/carbazoles from 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives using DPPE as a reducing agent

A green and efficient preparation of functionalized δ-carbolines/carbazoles via reductive ring closure by 1,2-bis(dipenylphosphino)ethane under solvent-free conditions is described. The starting materials 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives are readily prepared through Suzuki–Miyau...

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Veröffentlicht in:Tetrahedron 2011-08, Vol.67 (32), p.5725-5731
Hauptverfasser: Peng, Haixia, Chen, Xuxing, Chen, Yanhong, He, Qian, Xie, Yuyuan, Yang, Chunhao
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Sprache:eng
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Zusammenfassung:A green and efficient preparation of functionalized δ-carbolines/carbazoles via reductive ring closure by 1,2-bis(dipenylphosphino)ethane under solvent-free conditions is described. The starting materials 3-nitro-2-phenylpyridines/2-nitrobiphenyl derivatives are readily prepared through Suzuki–Miyaura cross-coupling reaction from commercially available compounds. And the polar by-product ethane-1,2-diylbis(diphenylphosphine oxide) is easily removed from the relatively polar reaction mixture. Various substituted δ-carbolines/carbazoles are obtained in acceptable yields. It is particularly worth mentioning that substrates with electron-withdrawing groups (EWG) also give the desired products in good yield. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.06.027