Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines: One-Pot, Three-Component Synthesis of Furo[2,3-d]pyridazin-4(5H)-ones

Mariateresa Giustiniano; Valentina Mercalli; Jussara Amato; Ettore Novellino; Gian Cesare Tron

doi:10.1021/acs.orglett.5b01798

Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines: One-Pot, Three-Component Synthesis of Furo[2,3-d]pyridazin-4(5H)-ones

Org Lett. 2015 Aug 21;17(16):3964-7. doi: 10.1021/acs.orglett.5b01798. Epub 2015 Aug 5.

Authors

Mariateresa Giustiniano¹, Valentina Mercalli², Jussara Amato¹, Ettore Novellino¹, Gian Cesare Tron²

Affiliations

¹ †Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy.
² ‡Dipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale "A. Avogadro", Largo Donegani 2, 28100 Novara, Italy.

PMID: 26244260
DOI: 10.1021/acs.orglett.5b01798

Abstract

An expeditious multicomponent reaction to synthesize tetrasubstituted furo[2,3-d]pyridazin-4(5H)-ones is reported. In brief, hydrazonoyl chlorides react with isocyanoacetamides, in the presence of TEA, to give 1,3-oxazol-2-hydrazones which, without being isolated, can react with dimethylacetylene dicarboxylate to afford furo[2,3-d]pyridazin-4(5H)-ones with an unprecedented level of complexity in a triple domino Diels-Alder/retro-Diels-Alder/lactamization reaction sequence.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Cycloaddition Reaction
Heterocyclic Compounds, 2-Ring / chemical synthesis*
Heterocyclic Compounds, 2-Ring / chemistry
Hydrazones / chemical synthesis
Hydrazones / chemistry
Imines / chemistry*
Molecular Structure
Nitriles / chemistry*
Stereoisomerism

Substances

Alkynes
Heterocyclic Compounds, 2-Ring
Hydrazones
Imines
Nitriles
dimethylacetylene