Construction of novel penta cyclic indolo-furo[3,2-c]quinoline and dihydrochromeno-furo[2,3-b]indol via sequential annulation strategy

[Display omitted] An efficient, rapid and green synthesis of indolo-furo-quinoline and chromeno-furo-indoles has been developed by one-pot reaction of 2,4-quinolinediol or 4-hydroxycoumarin, phenylglyoxal and aromatic amine in the presence of acetic acid as an reaction medium cum promoter at room te...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2022-10, Vol.109, p.154158, Article 154158
Main Authors: Yadav, Maruti B., Jeong, Yeon Tae
Format: Article
Language:English
Subjects:
Diastereoselective
Dihydrochromeno-furo[2,3-b]indol
Indolo-furo[3,2-c]quinoline
Multicomponent reactions (MCRs)
Stereogenic
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:[Display omitted] An efficient, rapid and green synthesis of indolo-furo-quinoline and chromeno-furo-indoles has been developed by one-pot reaction of 2,4-quinolinediol or 4-hydroxycoumarin, phenylglyoxal and aromatic amine in the presence of acetic acid as an reaction medium cum promoter at room temperature. This scalable tandem reaction affords a series of novel dihydro-indolo-furo-quinoline and dihydro-chromeno-furo-indole derivatives with two adjacent stereogenic centers in good to excellent yields and with high regioselectivity and stereoselectivity. Moreover, this cascade reaction provides a distinct Knoevenagel, Michael and through intramolecular cyclization in sequential manner under mild reaction conditions to access the diversely decorated indolo-furo-quinoline and chromeno-furo-indoles of considerable importance to natural product synthesis and medicinal chemistry.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.154158