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Synthesis 2025; 57(04): 855-875
DOI: 10.1055/a-2493-3436
DOI: 10.1055/a-2493-3436
paper
Consecutive Sonogashira–Suzuki–Michael Cyclization: Three-Component Synthesis of Phenanthridines and Benzo[c]chromenes
Authors
The authors gratefully acknowledge financial support by the Fonds der Chemischen Industrie.
Dedicated to Prof. Dr. Hans-Ulrich Reissig on the occasion of his 75th birthday
Abstract
The equistoichiometric three-component reaction of an acid chloride, an alkyne, and an ortho-amino- or ortho-hydroxyphenylboronic ester proceeds smoothly to give phenanthridines or benzo[c]chromenes, respectively, with good to quantitative yields in the sense of a Sonogashira–Suzuki–Michael cyclization sequence. In the coupling of ortho-amidophenylboronates, interestingly, after ring closure a subsequent an acyl migration occurs to give 6-(2-(acyloxy)vinyl)phenanthridines.
Key word
alkynylation - catalysis - multicomponent reaction - Michael addition - phenanthridines - benzo[c]chromenes - rearrangement - palladiumSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2493-3436.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 18. Oktober 2024
Angenommen nach Revision: 29. November 2024
Accepted Manuscript online:
29. November 2024
Artikel online veröffentlicht:
02. Januar 2025
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