Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins-Reference-Cited by-同舟云学术

Pd-Catalyzed N–H or C–H Functionalization/Oxidative Cyclization for the Efficient Synthesis of N-Aryl-Substituted [3,4]-Fused Pyrrolocoumarins

Published:2022-03-09 Issue:12 Volume:54 Page:2894-2806
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Litinas Konstantinos E.¹^ORCID,Balalas Thomas D.¹,Kanelli Maria G.¹,Gabriel Catherine²,Pontiki Eleni³,Hadjipavlou-Litina Dimitra J.³

Affiliation:

1. Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki

2. Center for Research of the Structure of Matter, Magnetic Resonance Laboratory, Department of Chemical Engineering, Aristotle University of Thessaloniki

3. Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki

Abstract

Abstract1-Aryl-2-methyl- or 3-methylchromeno[4,3-b]pyrrol-4(1H)-ones have been synthesized in excellent yields by the Pd-catalyzed intramolecular aza-Wacker-type cyclization of 3-allyl-4-arylaminocoumarins or C–H insertion/oxidative cyclization of N-allyl-N-aryl-4-aminocoumarins, respectively, in the presence of Cu(OAc)2 in acetic acid under heating. The starting allylcoumarins have been prepared by the allylation of 4-arylaminocoumarins with allyl bromide in CH3CN in the presence of Cs2CO3 at room temperature. Preliminary biological tests indicated interesting antioxidant activity and significant levels of inhibition of soybean lipoxygenase.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1610793.pdf

Reference10 articles.

1. In-silico fragment-based identification of novel angiogenesis inhibitors

2. One-pot synthesis of a natural product inspired pyrrolocoumarine compound collection by means of an intramolecular 1,3-dipolar cycloaddition as key step

3. A new method for the synthesis of plurisubstituted pyrroles

4. Phosphine-Catalyzed [3 + 2] Cycloaddition of Sulfamate-Derived Cyclic Imines with Allenoate: Synthesis of Sulfamate-Fused Dihydropyrroles

5. Condensed benzopyrans III.3H,4H[1] benzopyrano [3,4-b] pyrrol-4-ones

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