Novel Approaches for the Synthesis of a Library of Fluorescent Chromenopyrimidine Derivatives

Abstract

A library of some new fluorescent chromenopyrimidine derivatives has been synthesized by new approaches. Water-promoted and one-pot reaction can produce new dialkylylamino)-5H-chromeno[2,3-d]pyrimidin-2-yl) phenols. These compounds can also be produced using domino reaction. Two parallel methods are compared. Novel N-alkyl-N-phenyl-5H-chromeno[2,3-d]-pyrimidin-4-amines and 4-alkoxy-5H-chromeno[2, 3-d]pyrimidines are synthesized by Lewis-acid catalyzed reactions. The fluorescence emission intensity of the four compounds from each of libraries after excitation in 290 nm is measured. Compound 2-(4,5-bis(N-methyl-N-phenylamino)-5H-chromeno[2,3-d]pyrimidin-2-yl)phenol was isolated as a byproduct. The details of an interesting exchangeable intramolecular H- bonding of two of the new compounds are reported by X-ray analysis data.

Steroidal[17,16-d]pyrimidines derived from dehydroepiandrosterone: A convenient synthesis, antiproliferation activity, structure-activity relationships, and role of heterocyclic moiety

“…It is well known that pyrimidine core has wide occurrence in nature4, and which has also represent a typical class of heterocyclic scaffold in various compounds applied in the field of medicinal chemistry56789101112131415, agrochemicals161718192021222324, and materials2526272829. Up to now, many pyrimidines analogues have been demonstrated to exhibit wide pharmacological activities mainly including anticancer, antiviral, antibacterial, antimalarial, antituberculosis activities.…”

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

“…Recently, the one-pot three-component water-promoted synthesis of chromenopyrimidine 373 has been devised by Zonouzi et al [218] by heating aldehydes 370, The process is highly environmental benign, which proceeds in water in the absence of catalyst (Scheme 106). Amine derivatives 370 can be replaced by alcohol derivatives or malononitrile giving rise to the formation of respective pyrimidine derivatives.…”

Synthesis of Fluorescent 2,6‐Dicyano‐3,5‐Disubstituted Anilines Using Cellulose Sulfuric Acid in Aqueous Media

“…It seems that designing a highly efficient environmentally benign procedure for the preparation of fluorescent‐substituted cyanobenzene derivatives is of great interest. Following our interest in the synthesis of fluorescent compounds , here we wish to report the synthesis of fluorescent 2,6‐dicyano‐3,5‐dialkyl anilines using environmentally benign cellulose sulfuric acid as the catalyst in aqueous media ( Scheme ).…”