124
Views
5
CrossRef citations to date
0
Altmetric
Research Articles

The Chemical Behavior of (2E)-3-(4,9-Dimethoxy-5-Oxo-5H-Furo[3,2-g] Chromen-6-yl)Acrylonitrile Towards Some Carbon Nucleophiles

, , , &
Pages 1357-1368 | Received 18 Jun 2019, Accepted 04 Oct 2019, Published online: 18 Oct 2019
 

Abstract

Some novel substituted benzofurans and annulated furochromenes were obtained through the treatment of the novel (2E)-3-(4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromen-6-yl)acrylonitrile (Citation2) by some active carbon nucleophiles such as active methylene ketones and methylene nitriles. Thus, the reaction of acrylonitrile 2 with acetylacetone, ethyl acetoacetate, diethylmalonate, and acetoacetanilide in ethanol containing piperidine produced efficiently the corresponding polyfunctionalized benzonitrile derivatives 35 and furochromeno-pyridine 6, respectively. Also, treatment of acrylonitrile 2 with some methylene nitriles such as malononitrile, ethyl cyanoacetate, and malononitrile dimer afforded the annulated furochromene derivatives 79. Furthermore, the pyrido[1,2-a] benzimidazole system 10 was furnished via reaction of acrylonitrile 2 with 2-(1 H-benzimidazol-2-yl)acetonitrile. These reactions took place through Michael addition, retro-Michael, and γ-pyrone ring opening followed by different types of recyclization. The chemical structures of the novel products were established on the basis of their spectral data and elemental analysis.

Graphical Abstract

Correction Statement

This article has been republished with minor changes. These changes do not impact the academic content of the article.

Additional information

Funding

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through General Research Project under grant number (R.G.P1./22/40).

Log in via your institution

Log in to Taylor & Francis Online

PDF download + Online access

  • 48 hours access to article PDF & online version
  • Article PDF can be downloaded
  • Article PDF can be printed
USD 61.00 Add to cart

Issue Purchase

  • 30 days online access to complete issue
  • Article PDFs can be downloaded
  • Article PDFs can be printed
USD 1,492.00 Add to cart

* Local tax will be added as applicable

Related Research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.