293744-60-2Relevant academic research and scientific papers
Palladium(II)-catalyzed cyclizative cross-coupling of ortho-alkynylanilines with ortho-alkynylbenzamides under aerobic conditions
Yao, Bo,Wang, Qian,Zhu, Jieping
, p. 12992 - 12996 (2014/01/06)
Born to couple: The Pd(OAc)2-catalyzed reaction of o-alkynylanilines (1) with o-alkynylbenzamides (2) affords the cyclizative cross-coupling products 3 in good to excellent yields. Three bonds are created in the formation of two heterocycles tethered by a tetrasubstituted double bond. Mechanistic studies indicate that the reaction is initiated by aminopalladation with subsequent oxypalladation, N-demethylation, and reductive elimination. Copyright
Product selectivity control in the heteroannulation of o-(1-Alkynyl)benzamides
Bianchi, Gabriele,Chiarini, Marco,Marinelli, Fabio,Rossi, Leucio,Arcadi, Antonio
scheme or table, p. 136 - 142 (2010/06/20)
The selective synthesis of (Z)- or (E)-3-aryl/vinyl/alkylidene-isoindolones, and 2-benzopyran derivatives from o-(1-alkynyl)benzamides by means of a suitable choice of bases or silver catalysis is described.
Palladium-catalysed heteroannulation with terminal alkynes: A highly regio- and stereoselective synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1- ones
Kundu, Nitya G.,Khan, M. Wahab
, p. 4777 - 4792 (2007/10/03)
A highly regio- and stereoselective method for the synthesis of (Z)-3- aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)2PdCl2, CuI, and Et3N in DMF mostly at 80°C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd.
A highly regio and stereoselective synthesis of (Z)-3- aryl(alkyl)idene isoindolin-1-ones via palladium catalyzed annulation of terminal alkynes
Khan, M. Wahab,Kundu, Nitya G.
, p. 1435 - 1437 (2007/10/03)
o-Iodobenzamide or its N-substituted derivatives 4-10 and terminal alkynes 11-17 reacted in DMF in the presence of bis(triphenylphosphine)palladium(II)chloride, cuprous iodide and triethylamine leading to (Z)-3- arylidene isoindolin-1-ones (22, 24, 27 and 28) or o-alkynyl N-substituted benzamides (I). The latter could be cyclised with sodium in ethanol in a completely regio and stereoselective manner to (Z)-3-aryl(alkyl)idene isoindolin-1-ones 18-35.
