Literature DB >> 30905029

DBU-mediated annulation of 2-aryl-3-nitro-2H-chromenes with 1,3-cyclohexanediones for the synthesis of benzofuro[2,3-c]chromenone derivatives.

Chenlu Dai1, Zengyang Xie2, Xushun Qing1, Naili Luo1, Cunde Wang3.   

Abstract

The DBU-mediated annulations of 2-aryl-3-nitro-2H-chromenes with 1,3-cyclohexanediones have been developed. This reaction involves a highly efficient domino sequence consisting of regioselective intermolecular Michael addition, intramolecular nucleophilic addition and aromatization as key unit steps. The reaction appears to be general for a variety of 2-aryl-3-nitro-2H-chromenes and tolerates the presence of aromatic moieties with electron-withdrawing and electron-donating substituents. This transformation provides a straightforward synthetic protocol for constructing benzofuro[2,3-c]chromenone derivatives.

Entities:  

Keywords:  1,3-cyclohexanediones; 2-Aryl-3-nitro-2H-chromene; Annulation; Benzofuro[2,3-c]chromenone; DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)

Year:  2019        PMID： 30905029     DOI： 10.1007/s11030-019-09939-2

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  19 in total

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