Fine tuning the outcome of 1,3-dipolar cycloaddition reactions of benzimidazolium ylides to activated alkynes

Georgescu Emilian I.; Nicolescu Alina Florica; Georgescu Florentina; Teodorescu Florina Ruxandra; Shova Sergiu; Marinoiu Adriana; Dumitrascu Florea; Deleanu Călin

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GEORGESCU, Emilian I., NICOLESCU, Alina Florica, GEORGESCU, Florentina, TEODORESCU, Florina Ruxandra, SHOVA, Sergiu, MARINOIU, Adriana, DUMITRASCU, Florea, DELEANU, Călin. Fine tuning the outcome of 1,3-dipolar cycloaddition reactions of benzimidazolium ylides to activated alkynes. In: Tetrahedron, 2016, nr. 19(72), pp. 2507-2520. ISSN 0040-4020. DOI: https://doi.org/10.1016/j.tet.2016.03.086

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Tetrahedron

Numărul 19(72) / 2016 / ISSN 0040-4020 /ISSNe 1464-5416

Fine tuning the outcome of 1,3-dipolar cycloaddition reactions of benzimidazolium ylides to activated alkynes

DOI:https://doi.org/10.1016/j.tet.2016.03.086

Pag. 2507-2520

Georgescu Emilian I.¹, Nicolescu Alina Florica², Georgescu Florentina³, Teodorescu Florina Ruxandra², Shova Sergiu⁴⁵, Marinoiu Adriana⁶, Dumitrascu Florea², Deleanu Călin²⁴

¹ Centrul de Cercetare Oltchim, Ramnicu Valcea,
² "C.D. Nenitzescu" Centre of Organic Chemistry, Romanian Academy,
³ Teso Spec SRL,
⁴ “Petru Poni” Institute of Macromolecular Chemistry,
⁵ Institute of Chemistry of the Academy of Sciences of Moldova,
⁶ National Research and Development Institute for Cryogenics and Isotopic Technologies

Disponibil în IBN: 15 august 2022

Rezumat

1,3-Dipolar cycloaddition reactions of benzimidazolium ylides, generated from 3-phenacylbenzimidazolium bromides, to non-symmetrical activated dipolarophiles in various reaction conditions led to complex mixtures of pyrrolo[1,2-a]benzimidazole and pyrrolo[1,2-a]quinoxaline derivatives. In order to explain all experimental results, the influence of reaction conditions on the reaction products was investigated. For the first time, 4-hydroxy-4,5-dihydropyrrolo[1,2-a]quinoxaline derivatives 6, pyrrolo[1,2-a]quinoxalinium quaternary salts 8, as well as 4-methoxy-4,5-dihydropyrrolo[1,2-a]quinoxalines 9, were separated, fully characterized and their interconversions are presented, together with a proposed reaction mechanism.

Cuvinte-cheie
cycloaddition, Nitrogen heterocycles, Pyrrolo[1,2-a]benzimidazole, Pyrrolo[1,2-a]quinoxaline, Ylides

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<title xml:lang='en'>Fine tuning the outcome of 1,3-dipolar cycloaddition reactions of benzimidazolium ylides to activated alkynes</title>
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