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Issue 3, 2019
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Multicomponent synthesis of pyroglutamic acid derivatives via Knoevenagel–Michael-hydrolysis-lactamization-decarboxylation (KMHL-D) sequence

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Abstract

A novel and practical method for the synthesis of 3-substituted pyroglutamic acid derivatives is described. One pot multicomponent reaction of Meldrum's acid, aldehyde and Schiff's base followed an unprecedented chemoselective Knoevenagel–Michael-hydrolysis-lactamization domino sequence to afford 4-carboxy 3-substituted pyroglutamic acid derivatives under mild conditions. A carboxy intermediate formed appears to accelerate its own formation. The generality of the synthesis is exemplified by the use of a wide variety of aldehydes including enolizable aliphatic aldehydes, while substrates are stable under reaction conditions.

Graphical abstract: Multicomponent synthesis of pyroglutamic acid derivatives via Knoevenagel–Michael-hydrolysis-lactamization-decarboxylation (KMHL-D) sequence

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Publication details

The article was received on 04 Oct 2018, accepted on 18 Dec 2018 and first published on 18 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02473A
Citation: Org. Biomol. Chem., 2019,17, 561-566
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    Multicomponent synthesis of pyroglutamic acid derivatives via Knoevenagel–Michael-hydrolysis-lactamization-decarboxylation (KMHL-D) sequence

    T. M. Khopade, P. K. Warghude, A. D. Sonawane and R. G. Bhat, Org. Biomol. Chem., 2019, 17, 561
    DOI: 10.1039/C8OB02473A

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