Synthesis o? spiro[piperidine-4,3?-pyrrolo[3,4-c]quinolines via 1,3-dipolar cycloaddition o? azomethine ylides and 3-Nitro-2(1H)-quinolones

Molnár, M., Gáti, T., Bényei, A., Nyerges, M.: Synthesis o? spiro[piperidine-4,3?-pyrrolo[3,4-c]quinolines via 1,3-dipolar cycloaddition o? azomethine ylides and 3-Nitro-2(1H)-quinolones.
Tetrahedron Lett. 139, 1-6, (article identifier: 155001), 2024.

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Q3 Biochemistry

Q3 Drug Discovery

Q3 Organic Chemistry

title:

Synthesis o? spiro[piperidine-4,3?-pyrrolo[3,4-c]quinolines via 1,3-dipolar cycloaddition o? azomethine ylides and 3-Nitro-2(1H)-quinolones

authors:

Molnár Márk
Gáti Tamás
Bényei Attila
Nyerges Miklós

corresponding author:

Nyerges Miklós

published:

2024

type:

article

genre:

research article/review article

journal:

Tetrahedron Letters (ISSN: 0040-4039)

language:

English

HAC:

Natural Sciences, Chemical Sciences

subjects:

Azomethine ylide, 1,3-Dipolar Cycloaddition, Quinoline, Piperidine, X-ray diffraction

abstract:

The 1,3-dipolar cycloaddition of 3-nitro-2(1H)-quinolones and <U+00be>-nitro-styrenes with azomethine ylides derived from sarcosine and benzyl 4-oxopiperidine-1-carboxylate have been investigated. The structure of the formed cycloadducts were studied in detail by X-ray diffraction and NMR spectroscopy methods. This process is a solid and versatile strategy for rapidly assembling quinoline fused pyrrolines scaffold with a spiropiperidine part containing orthogonal diversification points for further substitutions.