A facile synthesis of chromeno[3,4-c]spiropyrrolidine indenoquinoxalines via 1,3-dipolar cycloadditions

Shahnaz Rahimi; Mehdi Ghandi; Maryam Fallahnezhad; Alireza Abbasi

doi:10.1007/s11030-023-10629-3

A facile synthesis of chromeno[3,4-c]spiropyrrolidine indenoquinoxalines via 1,3-dipolar cycloadditions

Mol Divers. 2024 Feb;28(1):133-142. doi: 10.1007/s11030-023-10629-3. Epub 2023 Mar 21.

Authors

Shahnaz Rahimi¹, Mehdi Ghandi², Maryam Fallahnezhad³, Alireza Abbasi³

Affiliations

¹ School of Chemistry, College of Science, University of Tehran, P.O. Box 14155 6455, Tehran, Iran. sh.rh1989@gmail.com.
² School of Chemistry, College of Science, University of Tehran, P.O. Box 14155 6455, Tehran, Iran. ghandi@khayam.ut.ac.ir.
³ School of Chemistry, College of Science, University of Tehran, P.O. Box 14155 6455, Tehran, Iran.

PMID: 36943611
DOI: 10.1007/s11030-023-10629-3

Abstract

A one-pot, four-component reaction for the synthesis of novel chromeno[3,4-c]spiropyrrolidine-indenoquinoxalines is described via a 1,3-dipolar cycloaddition of 3-acetyl-coumarins with the azomethine ylides followed by deacetylation and protonation (deuteration). The products were obtained in moderate to high yields, and their structures were confirmed by ¹H NMR, ¹³C NMR, FT-IR, and MS spectroscopy.

Keywords: 1,3-dipolar cycloaddition reaction; 3-acetyl-coumarins; azomethine ylides; one-pot reaction; spiropyrrolidine-indenoquinoxalines.

MeSH terms

Cycloaddition Reaction*
Magnetic Resonance Spectroscopy
Spectroscopy, Fourier Transform Infrared