Effect of Metal Ions in Organic Synthesis; Part XXIV. Facile One-Flask Synthesis of 1-Alkoxycarbonylamino-3-aminocarbonylpyrroles by Reaction of Alkoxycarbonylazoalkenes with 3-Oxoalkanamides under Copper(II) Chloride Catalysis

Attanasi, Orazio A.; Fïlippone, Paolino; Mei, Amedeo; Santeusanio, Stefania

doi:10.1055/s-1984-31005

Cited by 64 publications

(24 citation statements)

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“…1,2-Diaza-1,3-dienes 1a-l were synthesized as a mixture of E/Z isomers as previously reported. [27] Solvents were purchased and used without further purification with the exception of THF which was distilled over sodium hydroxide. Melting points were determined on open capillary tubes.…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

“…solution of the 4-aminocarbonyl DDs 1a-e or 4-alkoxycarbonyl DDs 1g-l as a mixture of E/Z isomers [27] (1.0 mmol) in tetrahydrofuran (10 mL), the cyclohexylamine 2a, the benzylamine 2b, the p-toluidine 2c, the p-anisidine 2d, or the n-butylamine 2g, (1.0 mmol) was added. The reaction was allowed to proceed under magnetic stirring at room temperature for 2-4 h in the case of 1a-c, e, g-l or under reflux for 4 h in the case of 1d, until the disappearance of the reagents (monitored by TLC).…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

“…The products 3a-i, o-ab were purified by silica gel chromatography (elution mixture: ethyl acetate/cyclohexane) and they were crystallized from ethyl acetate (see Supporting Information). With regard to the synthesis of the bis-a-aminocarbonyl-a-aminohydrazones 3j-n, to a solution of the 4-aminocarbonyl DDs 1b, e, f as a mixture of E/Z isomers [27] (2.0 mmol) in tetrahydrofuran (15 mL), the 1,4-diaminopropane 2e, or 1,6-diaminohexane 2f (1.0 mmol) was added dropwise. The reaction was allowed to proceed under magnetic stirring at room temperature for 2-4 h, until the disappearance of the reagents (monitored by TLC).…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

“…To a solution of 4-alkoxycarbonyl DDs 1g-l as a mixture of E/Z isomers [27] (1.0 mmol) in chloroform (10 mL), the benzylamine 2b (1.0 mmol) or the n-butylamine 2g was added. The reaction was allowed to proceed under magnetic stirring at room temperature for 2-4 h, until the disappearance of the reagents (monitored by TLC).…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

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Zinc(II) Triflate‐Catalyzed Divergent Synthesis of Polyfunctionalized Pyrroles

et al. 2011

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Abstract:The zinc(II) triflate-catalyzed synthesis of highly functionalized pyrroles is described. The sequence involves the preliminary preparation of aaminohydrazones by Michael addition of primary amines to 1,2-diaza-1,3-dienes. The treatment of these intermediates with dialkyl acetylenedicarboxylates produces a-(N-enamino)-hydrazones that are converted into the corresponding pyrroles. The substituents on the carbon in position four of 1,2-diaza-1,3-dienes drive the regioselectivity of the ring closure process. Starting from 4-aminocarbonyl-1,2-diaza-1,3-dienes only dialkyl 1-substituted 5-aminocarbonyl-1H-pyrrole-2,3-dicarboxylates are achieved by Lewis acid-catalyzed ring closure. A screening of several Lewis/Brønsted acid catalysts is performed. Zinc(II) triflate is the most efficient catalyst. Under similar reaction conditions, employing 4-alkoxycarbonyl-1,2-diaza-1,3-dienes, only 4-hydroxy-1H-pyrrole-2,3-dicarboxylates are synthesized. These latter reactions can be accomplished regioselectively also in one pot. Using 4-aminocarbonyl-1,2-diaza-1,3-dienes, diamines and dialkyl acetylenedicarboxylates the sequence provides the corresponding a,w-di(Npyrrolyl)alkanes.

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Section: Experimental Section General Remarksmentioning

confidence: 99%

Section: Experimental Section General Remarksmentioning

confidence: 99%

Section: Experimental Section General Remarksmentioning

confidence: 99%

Section: Experimental Section General Remarksmentioning

confidence: 99%

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Zinc(II) Triflate‐Catalyzed Divergent Synthesis of Polyfunctionalized Pyrroles

et al. 2011

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“…2-Hydroxy-1-aminopyrrolines, 14, and 1-aminopyrroles, 15, were synthesized by reaction of DBD, 1, with β-diketones, β-keto esters, 15,17,18,22,[29][30][31][32][33][34][35][36][37][38][39]42,43,67,90 β-keto amides, [8][9][10]18,22,28,38,[46][47][48][49]67 β-keto lactones, 37 β-keto phosphoranes, 55 β-nitro ketones, 61,67 β-keto sulfones, [50][51][52]67 β-cyano ketones, 58,59,67 remotely activated ketones, 60 β-keto phosphonates, 62 α,α-dichloroacetophenone, 13, 68 …”

Section: Heterocyclesmentioning

confidence: 99%

1,2-Diaza-1,3-butadienes: just a nice class of compounds, or powerful tools in organic chemistry? Reviewing an experience

Attanasi¹,

Crescentini²,

Fïlippone³

et al. 2003

Arkivoc

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A New Convenient Liquid- and Solid-Phase Synthesis of Quinoxalines from (E)-3-Diazenylbut-2-enes

Attanasi

Crescentini

Fïlippone

et al. 2001

HCA

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3-{[(tert-Butoxy)carbonyl]diazenyl}but-2-enoates react in tetrahydrofuran at room temperature with aromatic 1,2-diamines to give 3-methylquinoxaline-2-carboxylates. These products were also obtained in solidphase synthesis, by using polymer-bound 3-diazenylbut-2-enes.Introduction. ± In recent years, quinoxalines have received much attention owing to their biological activities [1]. The often diffused methods reported for their synthesis, in general, involve the condensation of aromatic 1,2-diamines with a-diketones [2]. Based on our previous experience on the chemistry of 3-diazenylbut-2-enes [3 ± 5], we considered a retrosynthetic route to readily obtain quinoxalines from these starting materials in one pot and under very mild conditions. In fact, we previously reported the easy nucleophilic attack of amino groups at the terminal C-atom of the heterodiene system to give the corresponding a-aminohydrazones by 1,4-addition [5]. In the case of further internal attack of a second amino group at the CNÀ hydrazone C-atom, followed by loss of the hydrazino residue, quinoxalines could be obtained.Our initial hypothesis was successfully verified, thus, we now report a new and convenient access to quinoxalines, not easily accessible by the classical methods, by reaction of 3-diazenylbut-2-enes with aromatic 1,2-diamines both via liquid-and solidphase procedure.

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Effect of Metal Ions in Organic Synthesis; Part XXIV. Facile One-Flask Synthesis of 1-Alkoxycarbonylamino-3-aminocarbonylpyrroles by Reaction of Alkoxycarbonylazoalkenes with 3-Oxoalkanamides under Copper(II) Chloride Catalysis

Cited by 64 publications

References 0 publications

Zinc(II) Triflate‐Catalyzed Divergent Synthesis of Polyfunctionalized Pyrroles

Zinc(II) Triflate‐Catalyzed Divergent Synthesis of Polyfunctionalized Pyrroles

1,2-Diaza-1,3-butadienes: just a nice class of compounds, or powerful tools in organic chemistry? Reviewing an experience

A New Convenient Liquid- and Solid-Phase Synthesis of Quinoxalines from (E)-3-Diazenylbut-2-enes

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