1,5-Hydride-Shift-Triggered Cyclization for the Synthesis of Unsymmetric Julolidines-Reference-Cited by-同舟云学术

1,5-Hydride-Shift-Triggered Cyclization for the Synthesis of Unsymmetric Julolidines

Published:2021-07-27 Issue:24 Volume:53 Page:4689-4699
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Mikhaylov Andrey A.¹²^ORCID,Shirokova Vasilissa V.¹³,Ikonnikova Viktoria A.¹³,Solyev Pavel N.⁴,Lushpa Vladislav A.¹,Korlyukov Alexander A.⁵,Volodin Alexander D.⁵,Baleeva Nadezhda S.¹,Baranov Mikhail S.¹^ORCID

Affiliation:

1. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

2. National Research University Higher School of Economics

3. Higher Chemical College, D.I. Mendeleev University of Chemical Technology of Russia

4. Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

5. Nesmeyanov Institute of Organoelement Compounds

Abstract

AbstractDirectly accessible 8-substituted tetrahydroquinolines undergo 1,5-hydride-shift-triggered cyclization to provide difficult to access julolidine derivatives in yields of 21–98% under scandium(III) triflate catalysis. Additionally, the scope of the reaction, several follow-up transformations and a remarkable side process discovered during optimization of the conditions are highlighted.

Funder

Russian Science Foundation

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1559-2728.pdf

Reference34 articles.

1. Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

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3. Molecular hyperpolarizabilities of coumarin dyes