Manipulating a Multicomponent Reaction: A Straightforward Approach to Chromenopyrazole Hybrid Scaffolds

Paraskevi M. Kasapidou; Tryfon Zarganes-Tzitzikas; Constantinos A. Tsoleridis; Julia Stephanidou-Stephanatou; Constantinos G. Neochoritis

doi:10.1055/s-0036-1589013

Synthesis, Table of Contents

Synthesis 2017; 49(16): 3619-3632
DOI: 10.1055/s-0036-1589013

paper

Manipulating a Multicomponent Reaction: A Straightforward Approach to Chromenopyrazole Hybrid Scaffolds

Authors

Paraskevi M. Kasapidou

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece

^bMedway School of Pharmacy, Universities of Greenwich and Kent at Medway, Chatham Maritime, Kent, ME4 4TB, UK
Tryfon Zarganes-Tzitzikas

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece

^cDepartment of Pharmacy, University of Groningen, Deusinglaan 1, 9700 AD Groningen, The Netherlands Email: k.neochoritis@rug.nl
Constantinos A. Tsoleridis

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece
Julia Stephanidou-Stephanatou

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece
Constantinos G. Neochoritis*

^aLaboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece

^cDepartment of Pharmacy, University of Groningen, Deusinglaan 1, 9700 AD Groningen, The Netherlands Email: k.neochoritis@rug.nl

Abstract

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Dedicated to Prof. C. A. Tsoleridis on the occasion of his 67^th birthday

Abstract

An easy access to hybrid bioactive molecules, such as the chromenopyrazoles, is described based on the three-component reactions of 3-formylchromones, arylhydrazines, and acetylenedicarboxylates. By manipulating the reaction, four different scaffolds can be derived in an easy, versatile, and robust fashion. To underscore the potential, generality, and diversity that can be generated, representative libraries of each scaffold were synthesized. Moreover, a comprehensive NMR analysis with full assignment of all ¹H and ¹³C NMR chemical shifts has been performed.

Key words

3-formylchromones - multicomponent reactions - chromenopyrazoles - microwave irradiation - hybrid molecules - zwitterions

Full Text

References

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