Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-a]isoquinoline Derivatives via a 1,2-Rearrangement Step

Obydennik, Arina Y.; Titov, Alexander A.; Listratova, Anna V.; Borisova, Tatiana N.; Rybakov, Victor B.; Voskressensky, Leonid G.; Varlamov, Alexey V.

doi:10.3390/ijms25021085

Open AccessCommunication

Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-a]isoquinoline Derivatives via a 1,2-Rearrangement Step

by

Arina Y. Obydennik

¹,

Alexander A. Titov

¹

,

Anna V. Listratova

¹,

Tatiana N. Borisova

¹,

Victor B. Rybakov

²,

Leonid G. Voskressensky

^1,* and

Alexey V. Varlamov

¹

Organic Chemistry Department, Science Faculty, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow 117198, Russia

²

Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow 119991, Russia

^*

Author to whom correspondence should be addressed.

Int. J. Mol. Sci. 2024, 25(2), 1085; https://doi.org/10.3390/ijms25021085

Submission received: 28 December 2023 / Revised: 10 January 2024 / Accepted: 11 January 2024 / Published: 16 January 2024

(This article belongs to the Special Issue Small Molecules with Spiro-Conjugated Cycles: Advances in Synthesis and Applications, 2nd Edition)

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Abstract

Here, An efficient approach to obtaining previously unknown furo[2′,3′:2,3]pyrrolo[2,1-a]isoquinoline derivatives from readily available 1-R-1-ethynyl-2-vinylisoquinolines is described. The reaction features a simple procedure, occurs in hexaflouroisopropanol and does not require elevated temperatures. It has been found that the addition of glacial acetic acid significantly increases the yields of the target spirolactone products. Using trifluoroethanol instead of hexaflouroisopropanol results in the formation of pyrido[2,1-a]isoquinolines.

Keywords: hexaflouroisopropanol; lactonic pyrrolo[2,1-a]isoquinolines; pyrido[2,1-a]isoquinolines; [1,2]-sigmatropic rearrangement; trifluoroethanol

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MDPI and ACS Style

Obydennik, A.Y.; Titov, A.A.; Listratova, A.V.; Borisova, T.N.; Rybakov, V.B.; Voskressensky, L.G.; Varlamov, A.V. Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-a]isoquinoline Derivatives via a 1,2-Rearrangement Step. Int. J. Mol. Sci. 2024, 25, 1085. https://doi.org/10.3390/ijms25021085

AMA Style

Obydennik AY, Titov AA, Listratova AV, Borisova TN, Rybakov VB, Voskressensky LG, Varlamov AV. Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-a]isoquinoline Derivatives via a 1,2-Rearrangement Step. International Journal of Molecular Sciences. 2024; 25(2):1085. https://doi.org/10.3390/ijms25021085

Chicago/Turabian Style

Obydennik, Arina Y., Alexander A. Titov, Anna V. Listratova, Tatiana N. Borisova, Victor B. Rybakov, Leonid G. Voskressensky, and Alexey V. Varlamov. 2024. "Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-a]isoquinoline Derivatives via a 1,2-Rearrangement Step" International Journal of Molecular Sciences 25, no. 2: 1085. https://doi.org/10.3390/ijms25021085

APA Style

Obydennik, A. Y., Titov, A. A., Listratova, A. V., Borisova, T. N., Rybakov, V. B., Voskressensky, L. G., & Varlamov, A. V. (2024). Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-a]isoquinoline Derivatives via a 1,2-Rearrangement Step. International Journal of Molecular Sciences, 25(2), 1085. https://doi.org/10.3390/ijms25021085

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Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-a]isoquinoline Derivatives via a 1,2-Rearrangement Step

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