Iminocoumarins are a group of chemicals consisting of a

coumarin Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered h ...

with an attached

imine In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bon ...

group. Many derivatives of 2-iminocoumarin are applied as luminescence indicators, laser dyes, also they are known as biologically active compounds. Furthermore, structural features of 2-iminopyrane cycle cause unusual reactivity of these compounds. Most of the reported transformations affect directly the iminopyrane cycle, and the iminogroup is the main target for nucleophilic and electrophilic attacks in many cases. However furthermore the iminogroup these compounds can contain other functional groups, which can participate in such interactions. Thus, vicinal arrangement of the imino and amide nucleophilic groups in 2-iminocoumarin-3-(thio)carboxoamides 4, 5 produces great opportunity to utilize these compounds as building blocks to construct different heterocyclic systems. Iminocoumarins can be formed by a variation of the

Knoevenagel condensation In organic chemistry, the Knoevenagel condensation () reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation. A Knoevenagel condensation is a nucleophilic addition o ...

by reaction of

salicylaldehyde Salicylic aldehyde (2-hydroxybenzaldehyde) is the organic compound with the formula (C7 H6 O2) C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily ...

with substituted acetonitriles.

References

{{reflist Coumarins Fluorescent dyes Imines