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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 20
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Articles

Study of 1,3-dipolar cycloaddition of amino-acid azomethines and Juglone

Vadym Syngaevskya Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Lviv, Ukraine
,
Andrew Karkhuta Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Lviv, UkraineORCID Iconhttps://orcid.org/0000-0003-2386-1973
ORCID Icon,
Sviatoslav Polovkovycha Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Lviv, UkraineORCID Iconhttps://orcid.org/0000-0002-7143-6931
ORCID Icon,
Andrzej Gzellab Department of Organic Chemistry, Poznan University of Medical Sciences, Poznan, Poland
,
Roman Lesykc Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Lviv, Ukraine;d Department of Public Health, Dietetics and Lifestyle Disorders, Faculty of Medicine, University of Information Technology and Management in Rzeszow, Rzeszow, PolandCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0002-3322-0080
ORCID Icon &
Volodymyr Novikova Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Lviv, Ukraine
Pages 3165-3173 | Received 09 May 2020, Published online: 24 Jul 2020
 
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Abstract

Novel 2,3,4,9-tetrahydro- and 4,9-dihydro-1H-benzo[f]isoindole derivatives were synthesized from Juglone and amino-acid azomethines in 74–85% yields via 1,3-dipolar cycloaddition. The stereo- and regioselectivity of cycloaddition was confirmed by NMR spectra and single-crystal X-ray diffraction analysis.

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Supplementary information

Supplementary data (spectral and analytical data for compounds 3a,b and 4) associated with this article can be found, in the online version, at http://dx.doi.org/10.1080/00397911.2020.1795880.

Acknowledgments

We would like to express the warmest appreciation to Erasmus + program aims to support actions in the fields of Education, Training, Youth and Sport for the period 2014–2020 and to Professor Arnaud Martel (Le Mans University, France) for support and assistance in conducting research.

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