Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2019 Apr 11;4(4):6637-6646.
doi: 10.1021/acsomega.9b00407. eCollection 2019 Apr 30.

Cascade Reaction of 1,1-Enediamines with 2-Benzylidene-1 H-indene-1,3(2 H)-diones: Selective Synthesis of Indenodihydropyridine and Indenopyridine Compounds

Qin Luo  1 , Rong Huang  1 , Qiang Xiao  1 , Ling-Bin Kong  1 , Jun Lin  1 , Sheng-Jiao Yan  1
Affiliations

Cascade Reaction of 1,1-Enediamines with 2-Benzylidene-1 H-indene-1,3(2 H)-diones: Selective Synthesis of Indenodihydropyridine and Indenopyridine Compounds

Qin Luo et al. ACS Omega. .

Abstract

A concise and environmentally friendly route for the synthesis of diverse indenodihydropyridines (3) via a cascade reaction of 1,1-eneamines (1) with benzylidene-1H-indene-1,3(2H)-diones (BIDs) (2) in ethanol media was developed. The targeted compounds were efficiently obtained by only filtration without any further post-treatment. In the one-step cascade reaction, C-C and C-N bonds were constructed. In addition, when 1,4-dioxane was used as a solvent and the mixture of 1,1-eneamines (1) was refluxed with benzylidene-1H-indene-1,3(2H)-diones (BIDs) (2) for about 12 h, indenopyridine compounds (4) were produced. Two kinds of indenopyridine derivatives 3-4 resulted from alternative solvents and temperatures. The reaction had the following features: mild temperature, atom economy, high yields, and potential biological activity of the product.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Biological activity of dihydropyridines.
Figure 2
Figure 2
Biological activity of indenopyridine derivatives and the targeted compounds 3–4.
Scheme 1
Scheme 1. Methods for the Construction of Indenopyridine Derivatives
Scheme 2
Scheme 2. Mechanism for the Synthesis of Target Compounds 3–4
See this image and copyright information in PMC

References

    1. An G.; Seifert C.; Li G. N-Phosphonyl/phosphinyl imines and group-assisted purification (GAP) chemistry/technology. Org. Biomol. Chem. 2015, 13, 1600–1617. 10.1039/c4ob02254h. - DOI - PubMed
    1. Yu F.-C.; Chen Z.-Q.; Hao X.-P.; Yan S.-J.; Huang R.; Lin J. Regioselective synthesis of 9,10-dihydro-6H-chromeno[4,3-d]imidazo-[1,2-a]pyridin-6-one derivatives. RSC Adv. 2014, 4, 6110–6115. 10.1039/c3ra46428h. - DOI
    1. Jiang Y.; Xu K.; Zeng C. Use of Electrochemistry in the Synthesis of Heterocyclic Structures. Chem. Rev. 2018, 118, 4485–4540. 10.1021/acs.chemrev.7b00271. - DOI - PubMed
    1. Song Q.-W.; Zhou Z.-H.; He L.-N. Efficient, selective and sustainable catalysis of carbon dioxide. Green Chem. 2017, 19, 3707–3728. 10.1039/C7GC00199A. - DOI
    1. Biemolt J.; Ruijter E. Advances in Palladium-Catalyzed Cascade Cyclizations. Adv. Synth. Catal. 2018, 360, 3821–3871. 10.1002/adsc.201800526. - DOI