Synthesis 2017; 49(16): 3619-3632
DOI: 10.1055/s-0036-1589013
paper
© Georg Thieme Verlag Stuttgart · New York

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

Paraskevi M. Kasapidou
a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece
b   Medway School of Pharmacy, Universities of Greenwich and Kent at Medway, Chatham Maritime, Kent, ME4 4TB, UK
,
Tryfon Zarganes-Tzitzikas
a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece
c   Department of Pharmacy, University of Groningen, Deusinglaan 1, 9700 AD Groningen, The Netherlands   Email: k.neochoritis@rug.nl
,
Constantinos A. Tsoleridis
a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece
,
Julia Stephanidou-Stephanatou
a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece
,
Constantinos G. Neochoritis*
a   Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece
c   Department of Pharmacy, University of Groningen, Deusinglaan 1, 9700 AD Groningen, The Netherlands   Email: k.neochoritis@rug.nl
› Author Affiliations
Further Information

Publication History

Received: 29 January 2017

Accepted after revision: 28 March 2017

Publication Date:
09 May 2017 (online)


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

Supporting Information