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Metal‐Free Synthesis of Pyrimidine and Naphthoquinone‐Fused Pyrroles from Arylglyoxal‐Based Domino Reactions by Anoop Kumar Panday; Danish Ali; Tasneem Parvin; Lokman H. Choudhury is a Chemistry article available to read on EtoBox.

What is Metal‐Free Synthesis of Pyrimidine and Naphthoquinone‐Fused Pyrroles from Arylglyoxal‐Based Domino Reactions about?

Herein we report acid mediated two and three-component domino reactions of cyclic enamines such as 2-amino-1,4naphthoquinone, and 6-amino-1,3-dimethyluracil with arylglyoxals for the synthesis of diverse fused pyrroles. The twocomponent reaction of arylglyoxal and 2-amino-1,4-naphthoquinone in the acetic acid medium provided substituted naphthoquinone-fused pyrroles tethered with hydroxyl and aryl substituents. On the other hand, under similar reaction conditions, the reaction of phenylglyoxal with 6-amino-1,3dimethyluracil provided an unusual bipyrrolopyrimidine with a quaternary carbon center following a domino reaction involving the formation of five new sigma bonds in one-pot. Interestingly, the reaction of arylglyoxals with 6-amino-1,3dimethyluracil in ethanol medium in the presence of 10-mol% PTSA provided a three-component product having pyrimidine fused pyrrole linked with 6-aminouracil moiety. We have also developed a three-component reaction of 2-amino-1,4-naphthoquinone, arylglyoxals, and 4-hydroxy-1-methylquinolin-2(1H)-one for the synthesis of naphthoquinone-fused pyrroles linked with hydroxyquinoline derivatives.

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Author

Anoop Kumar Panday; Danish Ali; Tasneem Parvin; Lokman H. Choudhury

Publisher

Wiley

Published

2023

Language

EN

Field

Chemistry (Physical Sciences)