Iminophosphorane-mediated synthesis of 1-substituted-β-carbolines: investigative studies on the preparation of alkaloids lavendamycin and eudistomins framework.

Molina, Pedro; Fresneda, Pilar M.; Cánovas, Manuel Fernández

doi:10.1016/s0040-4039(00)78888-5

Cited by 24 publications

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References 19 publications

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“…This kind of conversion takes place through two pathways: (i) a Michael type addition followed by proton transfer to generate an intermediate iminophosphorane which then undergoes an intramolecular aza-Wittig reaction and (ii) aza-Wittig reaction leading to an intermediate azahexatriene which then undergoes a thermal 6π-electrocyclization . In this sense, (vinylimino)phosphoranes of type 1 reacted with aliphatic, aromatic, and heteroaromatic aldehydes to give the corresponding 2-azahexatriene, which underwent electrocyclic ring-closure followed by dehydrogenation to give pyridines or isoquinoline derivatives 2 . However, the reaction with α,β-unsaturated aldehydes provided 3-arylpyridines 3 in a completely regioselective fashion …”

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Unusual Reactivity of (Vinylimino)phosphoranes and Their Utility in the Preparation of Pyridine and Dihydropyridine Derivatives

1996

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New reactions of (vinylimino)phosphoranes with aldehydes involving an initial nucleophilic attack of the beta-carbon atom of the vinyl side chain on the carbonyl carbon atom are reported. Iminophosphorane 4 derived from ethyl beta-azidoacrylate reacts with substituted cinnamyl aldehydes to give a mixture of 2-arylpyridine and 4-styryldihydropyridine derivatives, whereas the reaction with substituted benzaldehydes provides 4-aryldihydropyridine derivatives. However, the iminophosphorane 16 derived from the diethyl azidofumarate reacts with cinnamyl aldehydes through the expected aza-Wittig fashion to give 4-arylpyridine derivatives after dehydrogenation of the resulting dihydropyridine.

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confidence: 99%

Unusual Reactivity of (Vinylimino)phosphoranes and Their Utility in the Preparation of Pyridine and Dihydropyridine Derivatives

1996

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Aza‐Wittig Reaction in Natural Product Syntheses

et al. 2009

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Ascidians (Tunicates)–2

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Metabolites of Polyclinidae Long‐Chain Sulfated Alkanes and Terpenes of Sidnyum turbinatum Terpenes and Meroterpenes Para‐ and Metacyclophanes: Longithorones and Related Derivatives Simple Aromatic Derivatives Nitrogenous and Non‐Nitrogenous Macrolides Long‐Chain Amines and Amino Alcohols, Sphingosines Piperidine Alkaloids: Pseudodistomins Indole and β‐Carboline Alkaloids Quinoline and Pyridoacridine Alkaloids Bis‐Steroidal Alkaloids of Ritterella tokioka : Ritterazines Purines and Nucleosides Miscellaneous Nitrogenous Derivatives Metabolites of Ascidiidae Vanadium, Intracellular Acidity of Blood Cells, and Peptide Ligands Metabolites of Cionidae Metabolites of Diazonidae Metabolites of Perophoridae Metabolites Isolated from Species of the Genus Perophora Tetrahydroisoquinoline Alkaloids: Ecteinascidins Metabolites of Molgulidae and Pyuridae Lipids and Non‐Nitrogenous Derivatives Nitrogenous Derivatives, Antimicrobial Peptides, and Proteins Metabolites of Styelidae Non‐Nitrogenous Derivatives Phenylethylamine Derivatives, Various Alkaloids Antibacterial Purines and Peptides

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Iminophosphorane-mediated synthesis of 1-substituted-β-carbolines: investigative studies on the preparation of alkaloids lavendamycin and eudistomins framework.

Cited by 24 publications

References 19 publications

Unusual Reactivity of (Vinylimino)phosphoranes and Their Utility in the Preparation of Pyridine and Dihydropyridine Derivatives

Unusual Reactivity of (Vinylimino)phosphoranes and Their Utility in the Preparation of Pyridine and Dihydropyridine Derivatives

Aza‐Wittig Reaction in Natural Product Syntheses

Ascidians (Tunicates)–2

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