57303-20-5Relevant academic research and scientific papers
One-pot synthesis of amides from carboxylic acids activated using thionyl chloride
Leggio,Belsito,De Luca,Di Gioia,Leotta,Romio,Siciliano,Liguori
, p. 34468 - 34475 (2016/06/13)
A one-pot synthesis of secondary and tertiary amides from carboxylic acids and amines by using SOCl2 has been developed. Also when sterically hindered amines were used as the starting materials, excellent yields of the corresponding amides were obtained. The amidation of N-protected α-amino acids with secondary amines proceeds effectively with good yields. The process works well also in the presence of acid sensitive groups and occurs with almost complete retention of stereochemical integrity of chiral substrates. This protocol could be extended to industrial large-scale production processes.
Regioselective hydrocarbamoylation of 1-alkenes
Miyazaki, Yosuke,Yamada, Yuuya,Nakao, Yoshiaki,Hiyama, Tamejiro
supporting information; experimental part, p. 298 - 300 (2012/05/20)
Nickel/Lewis acid cooperative catalysis derived from [Ni(cod)2], AlEt3, and N-heterocyclic carbene (NHC) effects highly regioselective hydrocarbamoylation of 1-alkenes. Variously substituted formamides and 1-alkenes can be employed to give a range of linear alkanamides regioselectively.
Nickel-catalyzed cross-coupling of unactivated alkyl halides and tosylate carrying a functional group with alkyl and phenyl Grignard reagents
Singh, Surya Prakash,Terao, Jun,Kambe, Nobuaki
scheme or table, p. 5644 - 5646 (2011/02/25)
By the use of catalytic amounts of a nickel salt and a 1,3-butadiene, primary and secondary alkyl Grignard reagents undergo cross-coupling with alkyl bromides, iodide, and tosylate carrying a functional group such as amide, ester, and ketone at 0 °C in THF. The present procedure provides a simple, convenient, and practical method for construction of carbon chains in the presence of various functional groups. PhMgBr also gave the corresponding coupling product in a moderate yield.
Design, synthesis, antibacterial, and QSAR studies of myristic acid derivatives
Narasimhan, Balasubramanian,Mourya, Vishnukant,Dhake, Avinash
, p. 3023 - 3029 (2008/09/20)
A series of esters and amides of myristic acid was synthesized and tested in vitro for antibacterial activity against Gram-positive and Gram-negative bacteria. All the compounds showed activity comparable to that of the standard drug, ciprofloxacin. The structural characteristics governing antibacterial activity of myristic acid derivatives was studied using QSAR methodology. The results showed that the antibacterial activity could be modeled using the topological descriptor, valence molecular connectivity index. The predictive ability of the models was cross-validated by construction of a test set. The low residual activity and high cross-validated r2 values ( rcv2 ) observed indicated the predictive ability of the developed QSAR models.
A convenient method for the synthesis and one-pot reaction of acyl chlorides using a scavenging resin
Girard,Tranchant,Niore,Herscovici
, p. 1577 - 1580 (2007/10/03)
A simple, efficient and fast method for the preparation of acyl halides from fatty carboxylic acids using a solid phase scavenging approach is presented herein. The title compounds can then be isolated, used as a solution or react in one-pot to form esters and amides with good to excellent yields.
Nematocidal activity of long alkyl chain amides, amines and their derivatives on dog roundworm larvae
Kiuchi,Nishizawa,Kawanishi,Kinoshita,Ohsima,Uchitani,Sekino,Ishida,Kondo,Tsuda
, p. 3234 - 3244 (2007/10/02)
The nematocidal activity of amides and amines having a long alkyl chain against the second-stage larva of dog roundworm, Toxocara canis, was examined. Long chain acyl amides with smaller substituents on the nitrogen showed stronger activity and the activity of cyclic amine amides was stronger than that of acyclic ones. In a series of homologous amides, the activity was dependent on the alkyl chain length: it reached a maximum at an optimal chain length and decreased in both shorter and longer homologues. The relationship between the activity and hydrophobicity of the homologues was analysed by the use of the bilinear model. The hydrophobicity of a compound, which gives a maximal activity, was similar for all neutral amides, but amides which have an additional amine group in the molecule had different values. Tertiary amines and their salts having a long alkyl chain also showed nematocidal activities comparable to those of the corresponding amides. The salts killed the larva at concentrations lower than their critical micell concentration, suggesting that they behave as a single molecule for the nematocidal action.
