Consecutive Sonogashira–Suzuki–Michael Cyclization: Three-Component Synthesis of Phenanthridines and Benzo[c]chromenes

Dedicated to Prof. Dr. Hans-Ulrich Reissig on the occasion of his 75^th 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 - palladium

Publication History

Received: 18 October 2024

Accepted after revision: 29 November 2024

Accepted Manuscript online:
29 November 2024

Article published online:
02 January 2025

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