A facile and efficient
protocol has been
developed for mild construction of fused pyrimidines via
l
-proline-catalyzed reaction of 4-hydroxy coumarins, aldehydes, and
2-aminobenzothiazoles/urea. The reaction has been carried out rapidly
and efficiently in water under mild and metal-free conditions. Current
etiquette has efficiently synthesized the heterocycles and avoids
the use of hazardous solvents over conventional organic solvents.
A plausible reaction mechanism has been established in this study.
This study represents the first case in which
l
-proline as
a homogeneous catalyst has been explored in the synthesis of fused
pyrimidines in water in view of simple procedure and acceptable efficiency.
This method gives the target product in excellent yield with ease
of workup.
A conceptually new intramolecular Pauson-Khand reaction (IPKR) based general strategy has been demonstrated for the formal syntheses of isoboonein, iridomyrmecin and isoiridomyr-mecin from very cheap, commercially available starting material.
Fused pyrimidines composed of alternating heteroatoms and a pyrimidine moiety were synthesized efficiently using readily available starting material 4-hydroxycoumarin, aromatic aldehydes, and urea/thiourea at room temperature.
An elegant Diels–Alder based approach has been demonstrated for the first racemic total synthesis of gramineusquinone B, iso-merrilliaquinone, iso-magnoshinin and 2-epi-3,4-dihydro magnoshinin.
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