78394-11-3Relevant articles and documents
Organocatalyzed synthesis and biological activity evaluation of hybrid compounds 4H-pyrano[2,3-b]pyridine derivatives
Pham, Hoai-Thu,Martin, James P.,Le, Truong-Giang
supporting information, p. 1845 - 1853 (2020/06/01)
1,4-Dihydropyridines and 4H-pyran derivatives are common and important structures in various pharmaceutical compounds. Dihydropyridines are well-known moieties in compounds that have analgesic, fungicidal, and antibacterial activities and 4H-pyran structu
Organocatalyzed regioselective and enantioselective synthesis of 1,4- and 1,2-dihydropyridines
Le, Truong-Giang,Pham, Hoai-Thu,Martin, James P.,Chataigner, Isabelle,Renaud, Jean-Luc
supporting information, p. 2673 - 2684 (2020/08/07)
Herein, we introduce one of the first examples of asymmetric organocatalyzed synthesis of 1,2-dihydropyridines, affording enantioselective access to and partially solving regioselectivity challenges in the synthesis of dihydropyridines. We demonstrate that through modification of organocatalysts both 1,2- and 1,4-dihydropyridines (1,2- and 1,4-DHPs) can be obtained with high regioselectivity (ratio of 1,2-DHP/1,4-DHP from 95/5 to 0/100) and enantioselectivity (33% ee for 1,2-DHPs and up to 98% ee for 1,4-DHPs) in good yields (up to 87%).
Microwave-assisted palladium-catalyzed allylation of β-enaminones
Erray, Imen,Rezgui, Farhat,Oble, Julie,Poli, Giovanni
supporting information, p. 2196 - 2200 (2014/11/12)
A new palladium-catalyzed approach for the C-allylation of β-enaminones under microwave irradiation is reported. This methodology provides an easy access to a variety of α-allylated enaminones. The reaction takes place with the preservation of the enamine function, which is poised for further transformations towards nitrogen-containing heterocycles. Georg Thieme Verlag Stuttgart New York.
Development of small-molecule P-gp inhibitors of the N-benzyl 1,4-dihydropyridine type: Novel aspects in SAR and bioanalytical evaluation of multidrug resistance (MDR) reversal properties
Baumert, Christiane,Günthel, Marianne,Krawczyk, S?ren,Hemmer, Marc,Wersig, Tom,Langner, Andreas,Molnár, Joséf,Lage, Hermann,Hilgeroth, Andreas
, p. 166 - 177 (2013/02/23)
Novel series of N-benzyl 1,4-dihydropyridines have been prepared by facile syntheses. All relevant substituents of the molecular scaffold have been varied. The resulting compounds were biologically evaluated as P-glycoprotein (P-gp) inhibitors. Substitutions of the N-benzyl residue favour biological activity beside respective 3-ester functions. Most active compounds were further evaluated as multidrug resistance (MDR) modulators to restore the cytotoxic properties of varying daunorubicin applications.
Multi-component reaction of amines, alkyl propiolates, and ninhydrin: An efficient protocol for the synthesis of tetrahydro-dihydroxy-oxoindeno[1,2-b] pyrrole derivatives
Azizian, Javad,Hatamjafari, Farhad,Karimi, Ali Reza,Shaabanzadeh, Masoud
, p. 765 - 767 (2007/10/03)
A new protocol for the synthesis of a series of tetrahydrodihydroxy- oxoindeno[1,2-b]pyrrole from simple primary amines, alkyl propiolates, and ninhydrin was developed. The key step in the synthesis is an efficient three-component reaction of an amine wit
PHOTOLYSIS OF A 2-TETRAZENE FROM AN ENEHYDRAZINE
Luebbe, Fritz,Grosz, Klaus-Peter,Hillebrand, Wigbert,Sucrow, Wolfgang
, p. 227 - 228 (2007/10/02)
Photolysis of the 2-tetrazene 1 gives the triazole 2 by homolysis of one single N,N-bond.The formation of the other products 4 - 13 can be rationalized by regarding the aza-allyl radical 3 as a common precursor.