A One-Pot Synthesis of Fluoro α-Acylamino Amide-Xanthates via an IMCR-Post Transformation Strategy

Manuel A Rentería-Gómez,Tannya R Ibarra-Rivera,Rocío Gámez-Montaño

doi:10.3390/ecsoc-24-08421

Manuel A Rentería-Gómez, Tannya R Ibarra-Rivera + Show 1 more

Open Access

https://doi.org/10.3390/ecsoc-24-08421

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Abstract

A series of six novel amide-xanthate products containing several fluorine atoms were prepared in moderate to good yields (40–92%) via an isocyanide-based multicomponent reaction (IMCR) of 5-CR by Ugi-4CR followed by an SN2 sequence in a one-pot manner. The design of molecules with fluorine atoms is of interest in medicinal chemistry and a research line of our interest. The role of fluorine atoms in biological properties is well documented, improving bioavailability, lipophilicity, and metabolic resistance in bioactive molecules.

Highlights

Multicomponent reactions (MCRs) are defined as reactions in which three or more starting materials react to form a product where basically all or most of the atoms contribute to the newly formed product
Ugi-4CR products can exemplify a wide variety of substitution patterns and are precursors to the synthesis of peptidomimetics that have potential pharmaceutical applications [2]
In order to develop conditions for the synthesis of α-acylamino amide-xanthates, we started the optimization for the synthesis of the α-acylamino amide analogue 8d by reacting 4-methoxybenzylamine (4), 4-azido-2,3,5,6-tetrafluorobenzaldehyde (5), chloroacetic acid (6), and tert-butyl isocyanide (7) in methanol anhydrous

Summary

Introduction

Multicomponent reactions (MCRs) are defined as reactions in which three or more starting materials react to form a product where basically all or most of the atoms contribute to the newly formed product.

Results

Conclusion