Acid-mediated domino reaction of ortho-carbonylated alkynyl-substituted arylaldehydes with phenols: Rapid access to fused indeno[2, 1-c]chromen-7-one derivatives. Issue 24 (15th June 2017)

• Record Type: Journal Article
• Authors: Zhu, Hongbo; Cao, Ziping; Meng, Xin; Tian, Laijin; Chen, Guang; Sun, Xuejun; You, Jinmao
• Is Part Of: Tetrahedron. Volume 73:Issue 24(2017)
• Page Start: 3310
• Page End: 3315
• Publication Date: 2017-06-15
• Subjects: Alkynylbenzaldehyde -- Phenol -- Polycycle -- Indanone -- Acid catalysis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.04.041
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Acid-mediated domino reaction of ortho -carbonylated alkynyl-substituted arylaldehydes with phenols is described. The implement of this reaction can provide directly a variety of tetracyclic indeno[2, 1- c ]chromen-7-one products in good yields. The mechanism was proposed to be a domino indanone ring formation/ortho-alkylation of phenols/dehydrated cyclization for the formation of polycyclic skeleton. In addition, several interesting dimeric products containing a pentacyclic scaffold were also afforded stereoselectively albeit in moderate yields. The present transformations feature the use of simple acid catalyst, short reaction time and good substrate scope. Graphical abstract: