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Synthesis 2022; 54(07): 1857-1869
DOI: 10.1055/a-1638-5030
paper

I2/DMSO-Promoted Synthesis of Chromeno[4,3-b]quinolines through an Imine Formation/Aza-Diels–Alder/Aromatization Tandem Reaction under Metal-Catalyst- and Photosensitizer-Free Conditions

Angélica Peñaranda Gómez
a   Laboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia
,
Carlos E. Puerto Galvis 
a   Laboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia
,
Mario A. Macías
b   Crystallography and Chemistry of Materials, CrisQuimMat, Department of Chemistry, Universidad de los Andes, Carrera 1 No. 18A 10, Bogotá 111711, Colombia
,
Cristian Ochoa-Puentes
c   Laboratorio de Síntesis Orgánica Sostenible, Departamento de Química, Universidad Nacional de Colombia–Sede Bogotá, Carrera 45 No. 26-85, A.A. 5997, Bogotá, Colombia
,
Vladimir V. Kouznetsov  ∗
a   Laboratorio de Química Orgánica y Biomolecular, CMN, Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 Vía Refugio, Piedecuesta 681011, Colombia
› Author AffiliationsWe thank the Departamento Administrativo de Ciencia, Tecnología e Innovación (Colombian Institute for Science and Research, COLCIENCIAS) under the project No. 111574455595 contract 648-2017 for the financial support, and Universidad de Antioquia under contract 20730003-028-2018, as well as Fondo Nacional de Financiamiento para la Ciencia y la Tecnología y la Innovación 'Francisco José de Caldas­', Conv. 811, for fellowships.
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Abstract

A tandem approach was developed for the efficient synthesis of substituted chromeno[4,3-b]quinolines from arylamines and O-cinnamyl salicylaldehydes under metal-catalyst- and photosensitizer-free reaction conditions. Our protocol is based on an inexpensive I2/DMSO system in which molecular iodine first acts as a Lewis acid to promote the formation of the corresponding imine bearing the alkene moiety; then, this species fulfills a second role by catalyzing an intramolecular aza-Diels–Alder cycloaddition to generate the respective tetrahydrochromenoquinoline as an intermediate. Finally, the dual behavior of DMSO as an oxidant and as a solvent proved crucial at this stage, allowing the regeneration of I2 and promoting the aromatization of the tetrahydrochromenoquinoline intermediates to yield the desired 7-aryl-6H-chromeno[4,3-b]quinolines. This protocol is mild and easy to perform, features high step-economy (tandem process) and provides a new access to biologically important nitrogen- and oxygen-containing heterocyclic molecules.

Key words

chromeno[4,3-b]quinolines - imines - iodine - tandem reaction - aza-Diels–Alder reaction - oxidation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1638-5030.
  • Supporting Information

Primary Data

    Primary data for this article are available online at https://zenodo.org/record/5034221 and can be cited using the following DOI: 10.5281/zenodo.5034221.



Publication History

Received: 25 May 2021

Accepted after revision: 06 September 2021

Accepted Manuscript online:
06 September 2021

Article published online:
20 October 2021

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