5840-59-5Relevant articles and documents
α-Alkylation of arylacetonitriles with primary alcohols catalyzed by backbone modified N-heterocyclic carbene iridium(i) complexes
Arslan, Burcu,Gülcemal, Süleyman
, p. 1788 - 1796 (2021/02/16)
A series of backbone-modified N-heterocyclic carbene (NHC) complexes of iridium(i) (1d-f) have been synthesized and characterized. The electronic properties of the NHC ligands have been assessed by comparison of the IR carbonyl stretching frequencies of thein situprepared [IrCl(CO)2(NHC)] complexes in CH2Cl2. These new complexes (1d-f), together with previously prepared1a-c, were applied as catalysts for the α-alkylation of arylacetonitriles with an equimolar amount of primary alcohols or 2-aminobenzyl alcohol. The catalytic activities of these complexes could be controlled by modifying the N-substituents and backbone of the NHC ligands. The NHC-IrIcomplex1fbearing 4-methoxybenzyl substituents on the N-atoms and 4-methoxyphenyl groups at the 4,5-positions of imidazole exhibited the highest catalytic activity in the α-alkylation of arylacetonitriles with primary alcohols. Various α-alkylated nitriles and aminoquinolines were obtained in high yields through a borrowing hydrogen pathway by using 0.1 mol%1fand a catalytic amount of KOH (5 mol%) under an air atmosphere within significantly short reaction times.
Synthesis of non-symmetrical 3,4-diaryl-substituted pyrroles: Implementation for the preparation of lamellarin R
Zavala-Gómez, Héctor,Ramírez-Rodríguez, Armando,Vázquez, Alfredo
, p. 677 - 683 (2018/01/08)
A straightforward method for synthesising symmetrical and non-symmetrical 3,4-diaryl-substituted pyrroles is proposed, consisting of (i) the condensation reaction between phenylacetonitriles and aldehydes to give acrylonitriles, (ii) the conjugate additio
A Paal-Knorr approach to 3,4-diaryl-substituted pyrroles: Facile synthesis of lamellarins O and Q
Ramirez-Rodriguez, Armando,Mendez, Jose M.,Jimenez, Cristina C.,Leon, Fernando,Vazquez, Alfredo
, p. 3321 - 3326,6 (2012/12/12)
A very simple, yet efficient synthetic methodology, to obtain 3,4-diaryl-substituted pyrroles is described. The approach is based on the Knoevenagel condensation between arylacetonitriles and substituted aromatic aldehydes, followed by conjugate addition of cyanide to afford succinonitriles in excellent yields. The products thus obtained were subjected to DIBAL-H reduction, followed by cyclization under acidic conditions to produce the corresponding pyrroles in good overall yields. The utility of this protocol is exemplified by the synthesis of the marine alkaloids lamellarins O and Q.