Radical Cyclization Cascade Involving Ynamides: An Original Access to Nitrogen-Containing Heterocycles
- 22 November 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (26) , 5095-5097
- https://doi.org/10.1021/ol036177q
Abstract
A radical cascade involving a 5-exo-dig cyclization followed by a 6-endo-trig radical trapping transforms ynamides into heterogeneous polycyclic compounds in good yields. This leads interestingly to the formation of isoindols, isoindolinones, and pyridoisoindolones.Keywords
This publication has 18 references indexed in Scilit:
- Highly Stereoselective Saucy−Marbet Rearrangement Using Chiral Ynamides. Synthesis of Highly Substituted Chiral Homoallenyl AlcoholsOrganic Letters, 2003
- Highly Stereoselective Synthesis of Novel α-Haloenamides via a Mild and Efficient Hydrohalogenation of YnamidesOrganic Letters, 2003
- A Highly Efficient and Flexible Synthesis of Substituted Carbazoles by Rhodium-Catalyzed Inter- and Intramolecular Alkyne CyclotrimerizationsAngewandte Chemie International Edition in English, 2002
- The First Stereoselective Ficini−Claisen Rearrangement Using Chiral YnamidesOrganic Letters, 2002
- Rhodium(I)-Catalyzed [2+2+2] Cycloadditions with N-Functionalized 1-Alkynylamides: A Conceptually New Strategy for the Regiospecific Synthesis of Substituted IndolinesAngewandte Chemie International Edition in English, 1999
- N-Functionalized 1-Alkynylamides: New Building Blocks for Transition Metal Mediated Inter- and Intramolecular [2+2+1] CycloadditionsAngewandte Chemie International Edition in English, 1998
- Preparation of ortho‐aryl‐benzaldehyde derivatives via free‐radical ipso‐substitution of an amidomethyl groupHelvetica Chimica Acta, 1997
- Organosilanes as radical-based reducing agents in synthesisAccounts of Chemical Research, 1992
- Et3B-induced radical addition of R3SnH to acetylenes and its application to cyclization reactionJournal of the American Chemical Society, 1987
- Palladium-catalyzed substitutions of triflates derived from tyrosine-containing peptides and simpler hydroxyarenes forming 4-(diethoxyphosphinyl)phenylalanines and diethyl arylphosphonatesJournal of the American Chemical Society, 1987