Multicomponent Synthesis of 2-(2,4-Diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonic Acids in DMSO.

Yuliya E Ryzhkova,Michail N Elinson,Oleg I Maslov,Artem N Fakhrutdinov

doi:10.3390/molecules26226839

Yuliya E Ryzhkova, Michail N Elinson + Show 2 more

Open Access

https://doi.org/10.3390/molecules26226839

Copy DOI

Abstract

Dimethyl sulfoxide is a widely used solvent in organic synthesis and in the pharmaceutical industry because of its low cost, stability, and low toxicity. Multicomponent reactions are an advanced approach that has become an efficient, economical, and eco-friendly substitute for the conventional sequential multi-step synthesis of various biologically active compounds. This approach was adopted for the synthesis of previously unknown 2-(2,4-diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)malonic acids via transformation of salicylaldehydes, malononitrile dimer, and malonic acid. It was shown that the use of DMSO at room temperature makes it possible to synthesize previously unavailable compounds. The investigation of the reaction mechanism using 1H-NMR monitoring made it possible to confirm the proposed mechanism of the transformation. The structure of synthesized 5H-chromeno[2,3-b]pyridines was confirmed by 2D-NMR spectroscopy.

Highlights

Multicomponent reactions (MCRs) are an important methodological arsenal in synthetic and medicinal chemistry [1]
MCRs exhibit a very high bond-forming index (BFI) as several non-hydrogen atom bonds are formed in one synthetic transformation [3]
MCRs are the best strategy for the synthesis of complex heterocyclic structures

Summary

Introduction

Multicomponent reactions (MCRs) are an important methodological arsenal in synthetic and medicinal chemistry [1]. Chromeno[2,3-b]pyridines are one of the important classes of condensed heterocyclic compounds from the point of view of medicinal chemistry. The synthesis of a new type of chromeno[2,3-b]pyridines is an important goal for researchers. We have already published multicomponent syntheses of different types of chromeno[2,3-b]pyridines [17,18,19,20,21,22]. In the synthesis of chromeno[2,3-b]pyridines, both multistep classical and multicomponent methods [16] are applied. We have already published multicomponent synth2esoef s9 of different types of chromeno[2,3-b]pyridines [17,18,19,20,21,22].

E3 ntry 4 51

General Information

Conclusions