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Giustiniano M, Meneghetti F, Mercalli V, et al. Synthesis of aminocarbonyl N-acylhydrazones by a three-component reaction of isocyanides, hydrazonoyl chlorides, and carboxylic acids. Org Lett. 2014;16(20):5332-5doi: 10.1021/ol502515b.
Giustiniano, M., Meneghetti, F., Mercalli, V., Varese, M., Giustiniano, F., Novellino, E., & Tron, G. C. (2014). Synthesis of aminocarbonyl N-acylhydrazones by a three-component reaction of isocyanides, hydrazonoyl chlorides, and carboxylic acids. Organic letters, 16(20), 5332-5. https://doi.org/10.1021/ol502515b
Giustiniano, Mariateresa, et al. "Synthesis of aminocarbonyl N-acylhydrazones by a three-component reaction of isocyanides, hydrazonoyl chlorides, and carboxylic acids." Organic letters vol. 16,20 (2014): 5332-5. doi: https://doi.org/10.1021/ol502515b
Giustiniano M, Meneghetti F, Mercalli V, Varese M, Giustiniano F, Novellino E, Tron GC. Synthesis of aminocarbonyl N-acylhydrazones by a three-component reaction of isocyanides, hydrazonoyl chlorides, and carboxylic acids. Org Lett. 2014 Oct 17;16(20):5332-5. doi: 10.1021/ol502515b. Epub 2014 Sep 26. PMID: 25259417.
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Org Lett. 2014 Oct 17;16(20):5332-5. doi: 10.1021/ol502515b. Epub 2014 Sep 26.

Synthesis of aminocarbonyl N-acylhydrazones by a three-component reaction of isocyanides, hydrazonoyl chlorides, and carboxylic acids.

Organic letters

Mariateresa Giustiniano, Fiorella Meneghetti, Valentina Mercalli, Monica Varese, Francesco Giustiniano, Ettore Novellino, Gian Cesare Tron

Affiliations

  1. Dipartimento di Farmacia, Università di Napoli "Federico II" , via D. Montesano 49, 80131 Napoli, Italy.

PMID: 25259417 DOI: 10.1021/ol502515b

Abstract

A novel one-pot multicomponent synthesis of α-aminocarbonyl N-acylhydrazones starting from readily available hydrazonoyl chlorides, isocyanides, and carboxylic acids is reported. The strategy exploits the ability of the carboxylic acid as a third component to suppress all competing reactions between nitrile imines and isocyanides, channeling the course of the reaction toward the formation of this novel class of compounds.

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