54879-64-0Relevant articles and documents
Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides
Smith, Philip J.,Jiang, Yubo,Tong, Zixuan,Pickford, Helena D.,Christensen, Kirsten E.,Nugent, Jeremy,Anderson, Edward A.
supporting information, p. 6547 - 6552 (2021/08/30)
Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core.
Boron-Catalyzed N-Alkylation of Arylamines and Arylamides with Benzylic Alcohols
Guru, Murali Mohan,Thorve, Pradip Ramdas,Maji, Biplab
, p. 806 - 819 (2020/01/02)
A sustainable boron-based catalytic approach for chemoselective N-alkylation of primary and secondary aromatic amines and amides with primary, secondary, and tertiary benzylic alcohols has been presented. The metal-free protocol operates at low catalyst loading, tolerates several functional groups, and generates H2O as the sole byproduct. Preliminary mechanistic studies were performed to demonstrate the crucial role of boron catalyst for the activation of the intermediate dibenzyl ether and to identify the rate-determining step.
Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex
Yudasaka, Masaharu,Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika
supporting information, p. 1098 - 1102 (2019/05/16)
The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.