69261-54-7Relevant articles and documents
One-Pot Double-Annulation Strategy for the Synthesis of Unusual Fused Bis-Heterocycles
Abdul-Rashed, Shukree,Alachouzos, Georgios,Brennessel, William W.,Frontier, Alison J.
supporting information, p. 4350 - 4354 (2020/06/04)
A novel metal-free double-annulation cascade for the construction of unusual fused heterocyclic systems is described. This simple protocol enables the sequential assembly of two rings in one pot from two simple precursors. Acidic conditions promote the condensation and the intramolecular alkynyl Prins reaction of an enyne or arenyne alcohol with a cyclic hemiaminal to form a five-, six-, or seven-membered oxacycle followed by a seven-or eight-membered azacycle. In this transformation, chemical complexity is rapidly generated with the formation of three new bonds (one C-O, one C-C, and one C-N) in one synthetic operation. The strategy is modular and relatively general, providing access to a series of unique fused bicyclic scaffolds.
Decarboxylative alkynylation and cyanation of carboxylic acids using photoredox catalysis and hypervalent iodine reagents
Le Vaillant, Franck,Waser, Jér?me
, p. 226 - 230 (2017/06/27)
Alkynes and nitriles are important functional groups that serve as versatile building blocks in organic synthesis and find applications in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild conditions is, therefore, highly desirable. Herein, we disclose the decarb-oxylative alkynylation and cyanation of broadly available carboxylic acids using photoredox catalysis and hyper-valent iodine reagents. Choices of both catalysts and reagents were crucial. Computational and experimental studies revealed two different possible mechanisms that are dictated by the oxidation potential of the reagents: radical for alkynylation, ionic for cyanation.
A dual arylboronic acid-aminothiourea catalytic system for the asymmetric intramolecular hetero-michael reaction of α,β-unsaturated carboxylic acids
Azuma, Takumi,Murata, Akihiro,Kobayashi, Yusuke,Inokuma, Tsubasa,Takemoto, Yoshiji
supporting information, p. 4256 - 4259 (2014/10/15)
A bifunctional aminoboronic acid has been used to facilitate for the first time the intramolecular aza- and oxa-Michael reactions of α,β- unsaturated carboxylic acids. The combination of an arylboronic acid with a chiral aminothiourea allowed for these re
