ZnBr2 catalyzed domino Knoevenagel-hetero-Diels–Alder reaction: An efficient route to polycyclic thiopyranoindol annulated [3,4-c]quinolone derivatives

Various novel polycyclic thiopyranoindol annulated [3,4-c]quinolone derivatives were synthesized via domino Knoevenagel-hetero-Diels–Alder reactions of indoline-2-thions and novel N-acrylated anthranilaldehydes in refluxing ethanol as a solvent in the presence of 20 mol% ZnBr2 as a Lewis acid cataly...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 73; no. 21; pp. 3040 - 3047
Main Authors Kiamehr, Mostafa, Alipour, Batoul, Mohammadkhani, Leyla, Jafari, Behzad, Langer, Peter
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.05.2017
Elsevier
Subjects
3,4-Dihydroquinolone
Chemistry
Chemistry, Organic
Domino reaction
Indole
Indolin-2-thione
Knoevenagel-hetero-Diels–Alder
Physical Sciences
Science & Technology
ZnBr2 catalyzed
Indolin-2-thione
Knoevenagel-hetero-Diels–Alder
3,4-Dihydroquinolone
Indole
ZnBr2 catalyzed
Domino reaction
2-OXOQUINOLINE DERIVATIVES
DESIGN
NATURAL-PRODUCTS
ONE-POT
Knoevenagel-hetero-Diels-Alder
THIOPYRANOCOUMARIN DERIVATIVES
7-MEMBERED RING LACTAMS
FUSED INDOLES
RADICAL CYCLIZATION
SCAFFOLDS
PLATELET AGGREGATION INHIBITORS
Online AccessGet full text

Cover

More Information
Summary:Various novel polycyclic thiopyranoindol annulated [3,4-c]quinolone derivatives were synthesized via domino Knoevenagel-hetero-Diels–Alder reactions of indoline-2-thions and novel N-acrylated anthranilaldehydes in refluxing ethanol as a solvent in the presence of 20 mol% ZnBr2 as a Lewis acid catalyst. All reactions proceed with high yields with excellent regio- and stereoselectivity. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.04.017