Abstract
A three-component reaction of 4-hydroxycoumarin, aldehydes and aromatic amines in the presence of catalytic amounts of Bi(OTf)3 is reported. Photophysical studies of these molecules showed that coumarin-fused dihydroquinolines exhibit significant quantum yields.
Highlights
Multicomponent reactions (MCRs) have become a very popular and powerful strategy in modern organic synthesis for facile access to complex organic molecules, especially heterocyclic molecules, in a single-step reaction.[1]
In the absence of any catalyst and with water as the reaction medium, we did not observe any of the desired three-component product, even after 24 h of stirring at room temperature
We investigated the scope and general applicability of this methodology by synthesising coumarin-fused dihydroquinoline (CFDQ), a tetracyclic heterocyclic molecule, using different aldehydes and aromatic amines (Table 2)
Summary
Multicomponent reactions (MCRs) have become a very popular and powerful strategy in modern organic synthesis for facile access to complex organic molecules, especially heterocyclic molecules, in a single-step reaction.[1] Fused polycyclic heterocyclic molecules are an important class of organic molecule because of their widespread applications as pharmaceutical candidates, optical materials and sensors.[2] The coumarin moiety is abundant in various natural and synthetic products and has applications in both medicinal chemistry and optoelectronics.[3] Coumarin-fused polycyclic heterocyclic molecules have very interesting properties and the development of new methods for facile access to these molecules has received much attention. Yang et al.[4] recently reported the synthesis of coumarin-/pyrrolefused heterocyclic molecules and their photochemical and redoxswitching properties. Coumarin-/phenanthridine-fused heterocyclic molecules show interesting photochemical and thermochromic properties.[5] Red fluorescent dyes based on
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