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Synthesis 2022; 54(17): 3845-3857
DOI: 10.1055/a-1742-2005
DOI: 10.1055/a-1742-2005
special topic
Special Issue in memory of Prof. Ferenc Fülöp
Electrocyclization and Unexpected Reactions of Non-Stabilized α,β:γ,δ-Unsaturated Azomethine Ylides: Experimental and Theoretical Studies
This project was supported by National Research, Development and Innovation Fund of Hungary, financed under the (OTKA PD128612) funding scheme. The authors are grateful to the Bolyai Research Scholarship of the Hungarian Academy of Sciences (BO/799/21/7), the ÚNKP-21-5 new National Excellence Program, NVKP-16 (1-2016-0043), KFI-16 (1-2016-0177), KFI-18 (00097) and VKE-18 (00032) of the Ministry for Innovation and Technology from the Source of the National Research, Development and Innovation Fund for financial support.
Abstract
Versatile, two-step syntheses of dihydrodibenzo[c,e]azepines, carbazole derivatives, and other alkaloid-type drug-like scaffolds by in situ generated azomethine ylide-induced intramolecular electrocyclization reaction from commercially available materials are presented. The reaction mechanisms of transition-metal-free carbon–carbon bond formation and the role of the kinetic control, resulting in the good regioselectivity, were confirmed by theoretical calculations.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1742-2005.
- Supporting Information
Publication History
Received: 25 November 2021
Accepted after revision: 17 January 2022
Accepted Manuscript online:
17 January 2022
Article published online:
24 March 2022
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For reviews on 1,5- and 1,7-electrocyclizations of conjugated 1,3-dipoles, see: