Aryne-Mediated Synthesis of Oxygen Heterocycles and Application to Cysteine-Selective Trapping
- 1 January 2021
- journal article
- research article
- Published by The Japan Institute of Heterocyclic Chemistry in HETEROCYCLES
- Vol. 102 (1), 3-33
- https://doi.org/10.3987/rev-20-934
Abstract
The use of arynes as the highly reactive intermediates in organic synthesis has attracted substantial attention. Particularly, the introduction of ortho-(trimethylsilyl)aryl triflates as easily activatable aryne precursors led to growing activity in this field. Most reactions using these aryne precursors proceed through the addition of nucleophiles to arynes and the subsequent trapping with electrophiles to give the multisubstituted arenes with structural diversity and complexity. Based on our studies, this review highlights the insertion of arynes, generated from ortho-(trimethylsilyl)aryl triflates, into C=O pi-bond of formamides. Initially, the representative examples for formal [2+2] cycloaddition of arynes with the carbon-heteroatom double bond or the heteroatom-heteroatom double bond are shown. Next, the studies on the insertion of arynes into the N-C and C=O bonds of amide group including our three-component coupling reaction leading to oxygen heterocycles are summarized. The S(N)2' reaction of tricyclic oxygen heterocycles, obtained by three-component coupling reaction, was studied by using carbon and sulfur nucleophiles. The S(N)2' reaction was expanded to four-component coupling reaction. Finally, the application of tricyclic oxygen heterocycles to cysteine-selective trapping is described.Keywords
This publication has 143 references indexed in Scilit:
- Three-Component Coupling Reactions of Arynes for the Synthesis of Benzofurans and CoumarinsMolecules, 2014
- Addition of Cyclic Ureas and 1-Methyl-2-oxazolidone to Pyridynes: A New Approach to Pyridodiazepines, Pyridodiazocines, and PyridooxazepinesOrganic Letters, 2013
- N,N‐Dimethylformamide: A Multipurpose Building BlockAngewandte Chemie, 2012
- Total Syntheses of Chelidonine and Norchelidonine via an Enamide–Benzyne–[2 + 2] Cycloaddition CascadeOrganic Letters, 2012
- Intermolecular C−O Addition of Carboxylic Acids to ArynesOrganic Letters, 2010
- Synthesis of 2H-Indazoles by the [3 + 2] Cycloaddition of Arynes and SydnonesOrganic Letters, 2010
- Enamide-Benzyne-[2 + 2] Cycloaddition: Stereoselective Tandem [2 + 2]−Pericyclic Ring-Opening−IntramolecularN-Tethered [4 + 2] CycloadditionsOrganic Letters, 2009
- Site-Selective Glycosylation of Hemoglobin on Cys β93Bioconjugate Chemistry, 2008
- A Convergent and Enantioselective Synthesis of (+)-Amurensinine via Selective C−H and C−C Bond Insertion ReactionsJournal of the American Chemical Society, 2006
- REARRANGEMENT IN THE REACTION OF CHLOROBENZENE-1-C14 WITH POTASSIUM AMIDE1Journal of the American Chemical Society, 1953