A synthesis of fused acenaphthopyrrolizines via the 1,3-dipolar cycloaddition reaction of azomethine ylides with acetylenic esters.

Issa Yavari, Leila Baoosi, Mohammad R Halvagar

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Article in Molecular diversity, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

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2citing papers in PubMed

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2 citing papers in PubMed.

Catalyst-free synthesis of acenaphthoindolopyrimidine derivatives.Molecular diversity · 2023
Article
Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones.Molecules (Basel, Switzerland) · 2019
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3 authors.

Issa YavariDepartment of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran. yavarisa@modares.ac.ir.

Leila BaoosiDepartment of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran.

Mohammad R HalvagarDepartment of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

An efficient synthesis of tetraalkyl 6a-hydroxy-3-alkyl-3H,6aH-acenaphtho[1,2-g] pyrrolizine-1,2,5,6-tetracarboxylates via the 1,3-dipolar cycloaddition reaction of azomethine ylides (generated in situ from [Formula: see text]-amino acids and acenaphthylene-1,2-dione) with dialkyl acetylenedicarboxylates is described. When glycine was used instead of alanine, phenylalanine, valine, or isoleucine, dialkyl (E)-1[Formula: see text]-(1,4-dialkoxy-1,4-dioxobut-2-en-2-yl)-2-oxo-[Formula: see text],5[Formula: see text]-dihydro-2H-spiro [acenaphthylene-1,2[Formula: see text]-pyrrole]-3[Formula: see text],4[Formula: see text]-dicarboxylates were obtained. The steric effects of the [Formula: see text]-amino acids side chains may be responsible for their different behaviors.

Indexed as

AlkynesAzo CompoundsCycloaddition ReactionEstersModels, MolecularMolecular ConformationPyrrolesStereoisomerismThiosemicarbazonesAlkynesAzo CompoundsazomethineEstersPyrrolesThiosemicarbazones1, 3-Dipolar cycloaddition azomethine ylidesAcetylenic esterFused pyrrolizinesSpiro[acenaphthylenepyrrole]

Identifiers

PMID28084603

DOI10.1007/s11030-016-9721-8

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.